Login Register Cart 0
Generic placeholder image

Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Mini-Review Article

A Mini-Review on Pyridazine Analogs: Chemical and Pharmacological Potentials

Author(s): Saad Alghamdi and Mohammad Asif*

Volume 20, Issue 2, 2023

Published on: 17 June, 2022

Page: [100 - 123] Pages: 24

DOI: 10.2174/1570193X19666220329155551

Price: $65

Open Access Journals Promotions 2
Abstract

The pyridazinone derivatives have diverse biological potential and are easily synthesized. Due to this, researchers and chemists have paid attention to the design and development of novel and effective bioactive compounds. The substituted pyridazines have shown a wide range of pharmacological activities, such as analgesic, anti-inflammatory, antibacterial, antifungal, anticonvulsant, antidepressant, antianxiety, antitubercular, anti-malarial, anticancer, anti-HIV, platelet inhibitory, hypotensive, cardiotonic, etc. In the current circumstances, it can be concluded that pyridazinone derivatives have great prospects, which remain to be revealed.

Keywords: Chemistry, pyridazine, antibacterial, antifungal, anticonvulsant, anti-malarial, anticancer, biological activities.

Next »
Graphical Abstract

[1]
Deker Barton, F.R.S.; David Ollis, F.R.S. Chairman and deputy chairman of the editorial board. Comprehensive organic chemistry. In: The Synthesis Reaction of the Organic Compound; Matyus, P.; Czako, K., Eds., 1993; 3, p. 249.
[2]
Tsubaki, K.; Taniguchi, K.; Tabuchi, S.; Okitsu, O.; Hattori, K.; Seki, J.; Sakane, K.; Tanaka, H. A novel pyridazinone derivative as a nonprostanoid PGI2 agonist. Bioorg. Med. Chem. Lett., 2000, 10(24), 2787-2790.
[http://dx.doi.org/10.1016/S0960-894X(00)00571-0] [PMID: 11133092]
[3]
Wang, T.; Dong, Y.; Wang, L.C.; Chen, Z. Synthesis and bioactivity of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives. Arzneimittelforschung, 2007, 57(10), 641-646.
[PMID: 18074757]
[4]
Asif, M.; Alam, M. Study of heterocyclic-fused pyridazinone analogues having phosphodiestrase-IV inhibitor activities as anti-inflammatory agents. J. Med. Chem. Sci., 2020, 3(2), 109-117.
[5]
Abdelbaset, M.S.; Abdel-Aziz, M.; Abuo-Rahma, G.E.A.; Ramadan, M.; Abdelrahman, M.H. Pyridazinones and pyrrolones as promising Scaffolds in Medicinal Chemistry. J. Adv. Biomed. Pharm. Sci., 2019, 2(1), 19-28.
[http://dx.doi.org/10.21608/jabps.2018.5283.1023]
[6]
Tauquir Alam, M.; Asif, M. A review on analgesic and anti-inflammatory activities of various piperazinyl containing pyridazine derivatives. Prog. Chem. Biochem. Res., 2020, 3(2), 81-92.
[7]
EL-HashashM.A.; Essawy, A.; Sobhy Fawzy, A. Synthesis and antimicrobial activity of some novel heterocyclic candidates via Michael addition involving 4-(4-acetamidophenyl)-4-oxobut-2-enoic acid. Adv. Chem., 2014, 2014, 1-10.
[8]
Lee, J.; Shin, A.Y.; Lee, H.S. Isolation and synthesis of luffariellolide derivatives and evaluation of antibacterial activities against gram-negative bacteria. Bull. Korean Chem. Soc., 2017, 38(7), 804-807.
[http://dx.doi.org/10.1002/bkcs.11156]
[9]
Imran, M.; Nayeem, N. Synthesis and antihypertensive activity of some novel pyridazinones. Orient. J. Chem., 2016, 32(1), 267-274.
[http://dx.doi.org/10.13005/ojc/320129]
[10]
Boukharsa, Y.Z.; Taoufik, J.; Ansar, M. Pyridazin-3(2H)-ones: Synthesis, reactivity, applications in pharmacology and agriculture. J. Chem. Pharm. Res., 2014, 6, 297-310.
[11]
Jones, R.A.; Whitmore, A. The tautomeric properties of 6-(2-pyrrolyl)pyridazin-3-one and 6-(2-pyrrolyl)pyridazin-3-thione. ARKIVOC, 2007, 11, 114-119.
[12]
Asif, M.; Singh, A. Exploring potential, synthetic methods and general chemistry of pyridazine and pyridazinone: A brief introduction. Int. J. Chemtech Res., 2010, 2(2), 1112-1128.
[13]
Tisler, M.; Stanovic, B. Advance in Heterocyclic Chemistry; Katritzky Alan, R.; boulton, A.J., Eds.; academic press, 1979, pp. 408.
[14]
Anwair, M.A.; Károlyházy, L.; Szabó, D.; Balogh, B.; Kövesdi, I.; Harmat, V.; Krenyácz, J.; Gellért, A.; Takács-Novák, K.; Mátyus, P. Lipophilicity of aminopyridazinone regioisomers. J. Agric. Food Chem., 2003, 51(18), 5262-5270.
[http://dx.doi.org/10.1021/jf0343938] [PMID: 12926868]
[15]
Asif, M.; Alshehri, M.M.; Kamal, M.; Acharya, M. In-silico activities, toxicity profiles and dug-like properties of some pyridazinyl)benzenesulfonamides as a COX-inhibitor and antineoplastic agent. Lat. Am. J. Pharm., 2021, 40(8), 1762-1769.
[16]
Károlyházy, L.; Horváth, G.; Mátyus, P. A novel pyridazino-fused ring system: Synthesis of pyridazino[3,4-b]diazepam. Acta Pharm. Hung., 2001, 71(2), 168-170.
[PMID: 11862664]
[17]
Katrusiak, A.; Baloniak, S. Reactivity of 6-chloro-4- and 5-hydrazino-2-phenyl- 3(2H)-pyridazinones with Vilsmeier reagent. Tetrahedron, 1994, 50(45), 12933-12940.
[http://dx.doi.org/10.1016/S0040-4020(01)81212-6]
[18]
Miguel, F.B.; Monica, C.M.L.G.; Elena, P.M.; Berta, L. Beatriz, de P.T.; Ana, R.; Nuria, A.; Francisco, L.; Dolores, M. M.; Olivier, L.; Laurent, M. Pyrazolo[3,4-c]pyridazines as novel and selective inhibitors of cyclin-dependent kinases. J. Med. Chem., 2005, 48(22), 6843-6854.
[http://dx.doi.org/10.1021/jm058013g]
[19]
Siddiqui, A.A.; Kushnoor, A.; Wani, S.M. Synthesis and hypotensive activity of some 6-(substituted aryl)-4-methyl-2,3-dihydropyridazin-3-ones. Indian. J. Chem. Biol., 2004, 43B, 1574-1579.
[20]
Siddiqui, A.A.; Syed, R.A.; Mohammed, S.M.; Syed, A.H.; Mohammed, R.; Ravindra, K. Synthesis and in-vitro antifungal activity of 6-substituted-phenyl-2-{[(4′-substitutedphenyl-5í-thioxo)-1,2,4-triazol-3-yl]-methyl}-2,3,4,5-tetrahydro pyridazin-3-one derivatives. Acta Pol. Pharm., 2008, 65(2), 223-228.
[PMID: 18666429]
[21]
Halasz, B.D.; Monsieurs, K.; Elias, O.; Karolyhazy, L.; Tapolcsanyi, P.; Maes, B.U.; Riedl, Z.; Hajos, G.; Dommisse, R.A.; Lemiere, G.L.; Kosmrlj, J.; Matyus, P. Synthesis of 5H-pyridazino[4,5-b]Indoles and their benzofurane analogues utilizing an intramolecular Heck-Type Reaction. Tetrahedron, 2004, 60(10), 2283-2291.
[http://dx.doi.org/10.1016/j.tet.2004.01.024]
[22]
Wing, L.K.; Behanna, H.A.; Van Eldik, L.J.; Watterson, D.M.; Ralay Ranaivo, H.; Hantamalala, R.R. De novo and molecular target-independent discovery of orally bioavailable lead compounds for neurological disorders. Curr. Alzheimer Res., 2006, 3(3), 205-214.
[http://dx.doi.org/10.2174/156720506777632844] [PMID: 16842097]
[23]
Mizzoni, R.H.; Spoerri, P.E. Synthesis in the pyridazine series. I. Pyridazine and 3,6-dichloropyridazine. J. Am. Chem. Soc., 1951, 73(4), 1873-1874.
[http://dx.doi.org/10.1021/ja01148a537]
[24]
Abubshait, S.A. An efficient synthesis and reactions of novel indolylpyridazinone derivatives with expected biological activity. Molecules, 2007, 12(1), 25-42.
[http://dx.doi.org/10.3390/12010025] [PMID: 17693951]
[25]
Dogruer, D.S.; Sahin, M.F.; Kupeli, E.; Yesilada, E. Synthesis and analgesic and anti-inflammatory activity of new pyridazinones. Turk. J. Chem., 2003, 27, 727-738.
[26]
Li, Q.; Lin, G.; Liu, L.; Yang, Z.; Zhang, L.H. Methyl carbonium ion migration during the reaction of 4-chloro-5-methoxyl-3(2H)-pyridazinone with trifluoroethylation agents. Molecules, 2009, 14(2), 777-784.
[http://dx.doi.org/10.3390/molecules14020777] [PMID: 19223826]
[27]
D’Auria, M. Electrophilic substitutions and HOMOs in azines and purines. Tetrahedron Lett., 2005, 46(6), 333-6336.
[http://dx.doi.org/10.1016/j.tetlet.2005.07.033]
[28]
Pattison, G.; Sandford, G.; Yufit, D.S.; Howard, J.A.; Christopher, J.A.; Miller, D.D. Polysubstituted pyridazinones from sequential nucleophilic substitution reactions of tetrafluoropyridazine. J. Org. Chem., 2009, 74(15), 5533-5540.
[http://dx.doi.org/10.1021/jo9006943] [PMID: 19518071]
[29]
Imran, M.; Asif, M. Biologically active pyridazines and pyridazinone derivatives: A scaffold for the highly functionalized compounds. Russ. J. Bioorganic Chem., 2020, 46(5), 726-744.
[http://dx.doi.org/10.1134/S1068162020050155]
[30]
Asif, M.; Imran, M. Antitubercular and anticonvulsant activities of phenyl-di-hydropyridazinone derivatives containing 2-substituted amin-1-yl-methyl and 2-(2-1h-amin-1-yl) ethyl moieties. Anal. Chem. Lett., 2020, 10(3), 414-427.
[http://dx.doi.org/10.1080/22297928.2020.1776633]
[31]
El-Shehry, M.F.; Abu-Zied, K.M.; Ewies, E.F.; Awad, S.M.; Mohram, M.E. Synthesis of some novel azaheterocycles utilizing 3-(4-nitrobenzylidene)5-phenylfuran-2(3H)-one with expected antimicrobial activity. Der Pharma Chem., 2013, 5(5), 318-326.
[32]
Bashir, R.; Yaseen, S.; Ovais, S.; Ahmad, S.; Hamid, H.; Alam, M.S.; Samim, M.; Javed, K. Synthesis and biological evaluation of some novel sulfamoylphenyl-pyridazinone as anti-inflammatory agents (Part-II *). J. Enzyme Inhib. Med. Chem., 2012, 27(1), 92-96.
[http://dx.doi.org/10.3109/14756366.2011.577036] [PMID: 21612377]
[33]
Bansal, R.; Kumar, D.; Sharma, D.; Calle, C.; Carron, R. Synthesis and pharmacological evaluation of 6-arylpyridazinones as potent vasorelaxants. Drug Dev. Res., 2013, 74(5), 296-305.
[http://dx.doi.org/10.1002/ddr.21079]
[34]
Tan, O.U.; Ozadali Sari, K. Azolo[d]pyridazinones in medicinal chemistry. Future Med. Chem., 2021, 13(3), 287-311.
[http://dx.doi.org/10.4155/fmc-2020-0234] [PMID: 33275029]
[35]
Barberot, C.; Moniot, A.; Allart-Simon, I.; Malleret, L.; Yegorova, T.; Laronze-Cochard, M.; Bentaher, A.; Médebielle, M.; Bouillon, J.P.; Hénon, E.; Sapi, J.; Velard, F.; Gérard, S. Synthesis and biological evaluation of pyridazinone derivatives as potential anti-inflammatory agents. Eur. J. Med. Chem., 2018, 146, 139-146.
[http://dx.doi.org/10.1016/j.ejmech.2018.01.035] [PMID: 29407945]
[36]
Selvakumar, P.; Thennarasu, S.; Mandal, A.B. Synthesis of novel pyridopyridazin-3 (2H)-one derivatives and evaluation of their cytotoxic activity against mcf-7 cells. ISRN Org. Chem., 2014, 2014, 1-7.
[37]
Liu, Y.; Jin, S.; Peng, X.; Lu, D.; Zeng, L.; Sun, Y.; Ai, J.; Geng, M.; Hu, Y. Pyridazinone derivatives displaying highly potent and selective inhibitory activities against c-Met tyrosine kinase. Eur. J. Med. Chem., 2016, 108, 322-333.
[http://dx.doi.org/10.1016/j.ejmech.2015.11.042] [PMID: 26698536]
[38]
Abbas, S.H.; Abuo-Rahma, G.D.; Abdel-Aziz, M.; Aly, O.M.; Beshr, E.A.; Gamal-Eldeen, A.M. Synthesis, cytotoxic activity, and tubulin polymerization inhibitory activity of new pyrrol-2(3H)-ones and pyridazin-3(2H)-ones. Bioorg. Chem., 2016, 66, 46-62.
[http://dx.doi.org/10.1016/j.bioorg.2016.03.007] [PMID: 27016713]
[39]
Kummari, B.; Ramesh, P.; Parsharamulu, R.; Allaka, T.R.; Anantaraju, H.; Yogeeswari, P.; Balasubramanian, S.; Guggilapu, S.D.; Babu, B.N.; Anireddy, J.S. Design and synthesis of new etodolac-pyridazinones as potent anticancer agents using PB (OAC) 4 to assist N-N bond formation. ChemistrySelect, 2018, 3(18), 5050-5054.
[http://dx.doi.org/10.1002/slct.201800459]
[40]
Asif, M.; Singh, A.; Lakshmayya, B. In-vivo anticonvulsant and in-vitro antimycobacterial activities of 6-aryl pyridazine-3(2H)-one derivatives. Am. J. Pharmacol. Sci., 2014, 2(1), 1-6.
[http://dx.doi.org/10.12691/ajps-2-1-1]
[41]
Refaat, H.M.; Khalil, O.M.; Kadry, H.H. Synthesis and anti-inflammatory activity of certain piperazinylthienylpyridazine derivatives. Arch. Pharm. Res., 2007, 30(7), 803-811.
[http://dx.doi.org/10.1007/BF02978828] [PMID: 17703729]
[42]
Onkol, T.; Sahin, M.F.; Yildirim, E.; Erol, K.; Ito, S. Synthesis and antinociceptive activity of (5-chloro-2(3H)-benzoxazolon-3-yl) propanamide derivatives. Arch. Pharm. Res., 2004, 27(11), 1086-1092.
[http://dx.doi.org/10.1007/BF02975109] [PMID: 15595407]
[43]
Giovannoni, M.P.; Vergelli, C.; Ghelardini, C.; Galeotti, N.; Bartolini, A.; Dal Piaz, V. [(3-Chlorophenyl)piperazinyl-propyl]pyridazinones and analogues as potent antinociceptive agents. J. Med. Chem., 2003, 46(6), 1055-1059.
[http://dx.doi.org/10.1021/jm021057u] [PMID: 12620082]
[44]
Rubat, C.; Coudert, P.; Albuisson, E.; Bastide, J.; Couquelet, J.; Tronche, P. Synthesis of Mannich bases of arylidenepyridazinones as analgesic agents. J. Pharm. Sci., 1992, 81(11), 1084-1087.
[http://dx.doi.org/10.1002/jps.2600811108] [PMID: 1447709]
[45]
Russo, F.; Guccione, S.; Romeo, G.; Barretta, G.U.; Pucci, S.; Caruso, A.; Roxas, M.A. Cutuli, Research on heterocyclic compounds XXXI. Synthesis and anti-inflammatory activity of 2-arylimidazo[1,2a]pyrazine-3-carboxylic acids. Eur. J. Med. Chem., 1993, 28, 363-376.
[http://dx.doi.org/10.1016/0223-5234(93)90123-V]
[46]
Sato, M.; Ishizuka, Y.; Yamaguchi, A. Pharmacological investigations of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone (M 73101), a new analgesic and anti-inflammatory drug. Arzneimittelforschung, 1981, 31(10), 1738-1745.
[PMID: 6172134]
[47]
Pinna, G.A.; Sardu, F.; Curzu, M.M.; Satta, M.; Peana, A.; Cignarella, G.; Barlocco, D. Synthesis and pharmacological activity of 4-carbamoyl-5-aryl-6-methyl-4,5-dihydropyridazin-3(2H)-ones. Farmaco, 1992, 47(4), 449-463.
[PMID: 1388593]
[48]
Flouzat, C.; Bresson, Y.; Mattio, A.; Bonnet, J.; Guillaumet, G. Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones. J. Med. Chem., 1993, 36(4), 497-503.
[http://dx.doi.org/10.1021/jm00056a010] [PMID: 8386248]
[49]
Piaz, V.D.; Giovannoni, M.P.; Ciciani, G.; Barlocco, D.; Giardina, G.; Petrone, G.; Clarke, G.D. 4,5-Functionalized 6-phenyl-3(2H)-pyridazinones: synthesis and evaluation of antinociceptive activity. Eur. J. Med. Chem., 1996, 31(1), 65-70.
[http://dx.doi.org/10.1016/S0223-5234(96)80008-0]
[50]
Pieretti, S.; Dal Piaz, V.; Matucci, R.; Giovannoni, M.P.; Galli, A. Antinociceptive activity of a 3(2H)-pyridazinone derivative in mice. Life Sci., 1999, 65(13), 1381-1394.
[http://dx.doi.org/10.1016/S0024-3205(99)00377-X] [PMID: 10503957]
[51]
Santagati, N.A.; Duro, F.; Caruso, A.; Trombadore, S.; Amico-Roxas, M. Synthesis and pharmacological study of a series of 3(2H)-pyridazinones as analgesic and antiinflammatory agents. Farmaco, Sci., 1985, 40(12), 921-929.
[PMID: 3879223]
[52]
Richard, R.H.; Lawrence, B.; Sekhar, S.; Teodozyj, K.; Sandra, M.; Marian, T.; George, G.; Victoria, K.; Denise, W.; Linda, K.; Kennan, M.; Michael, F.J. Merrill, Hugh, Lee, P.; Glenn, A.R.; Bryan, C.; Peer, J.; Andrew, S.; Michael; George, C.; Randy, L.B. ABT-963,2-(3,4-Difluoro-phenyl)-4-(3-hydroxy-3-methyl-butoxy)-5-(4-methanesul fonyl-phenyl)-2H-pyridazin-3-one, A highly potent and selective disubstituted pyridazin-one cyclooxgenase-2 inhibitor. J. Pharmacol. Exp. Ther., 2004, 311(3), 904-912.
[http://dx.doi.org/10.1124/jpet.104.070052] [PMID: 15277581]
[53]
Biancalani, C.; Giovannoni, M.P.; Pieretti, S.; Cesari, N.; Graziano, A.; Vergelli, C.; Cilibrizzi, A.; Di Gianuario, A.; Colucci, M.; Mangano, G.; Garrone, B.; Polenzani, L.; Dal Piaz, V. Further studies on arylpiperazinyl alkyl pyridazinones: Discovery of an exceptionally potent, orally active, antinociceptive agent in thermally induced pain. J. Med. Chem., 2009, 52(23), 7397-7409.
[http://dx.doi.org/10.1021/jm900458r] [PMID: 19788200]
[54]
Erden, B.; Murat, S.; Burcu, U.C.; Alis Ergun, K.; Sultan, B.; Eda, A.; Mustafa, A.R.K. Synthesis of the amide derivatives of 3-[1-(3-pyridazinyl)-5-phenyl-1H-pyrazole-3-yl]propanoic acids as potential analgesic compounds. Turk. J. Chem., 2007, 31, 677-687.
[55]
Pieretti, S.; Dominici, L.; Di Giannuario, A.; Cesari, N.; Dal Piaz, V. Local anti-inflammatory effect and behavioral studies on new PDE4 inhibitors. Life Sci., 2006, 79(8), 791-800.
[http://dx.doi.org/10.1016/j.lfs.2006.02.026] [PMID: 16546218]
[56]
Cignarella, G.; Grella, G.; Loriga, M.; Curzu, M.M.; Schiatti, G. [Unexpected anti-inflammatory activity of rigid structure derivatives of 6-arylpyridazinone antihypertensives. I. Synthesis and activity of 4,4a-dihydro-5H-indeno[1,2c]pyridazin-3-ones]. Farmaco, Sci., 1978, 33(11), 866-874.
[PMID: 744241]
[57]
Süküroglu, M.; Caliskan Ergün, B.; Unlü, S.; Sahin, M.F.; Küpeli, E.; Yesilada, E.; Banoglu, E. Synthesis, analgesic, and anti-inflammatory activities of [6-(3,5-dimethyl-4-chloropyrazole-1-yl)-3(2H)-pyridazinon-2-yl]acetamides. Arch. Pharm. Res., 2005, 28(5), 509-517.
[http://dx.doi.org/10.1007/BF02977751] [PMID: 15974435]
[58]
Ayla, B.; Fügen, O.; Oya, U.; Zafer, G.; Berna, T. Studies on Some 3-Oxo-5-benzylidene-6-methyl-(4H)-2–substitutedpyridazines with antinociceptive and anti- inflammatory activities. Fabad J. Pharm. Sci., 2003, 28, 19-25.
[59]
Gökçe, M.; Colak, M.S.; Küpeli, E.; Sahin, M.F. Synthesis and analgesic and anti-inflammatory activity of 6-phenyl/(4-methylphenyl)-3(2H)-pyridazinon-2-propionamide derivatives. Arzneimittelforschung, 2009, 59(7), 357-363.
[PMID: 19728563]
[60]
Gökçe, M.; Utku, S.; Küpeli, E. Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p-substituted/nonsubstituted benzal)hydrazone derivatives. Eur. J. Med. Chem., 2009, 44(9), 3760-3764.
[http://dx.doi.org/10.1016/j.ejmech.2009.04.048] [PMID: 19535179]
[61]
Abou-Zeid, K.A.M.; Youssef, K.M.; Shaaban, M.A.; El-Telbany, F.A.; Al-Zanfaly, S.H. Synthesis of 6-(4-(substituted-amino)phenyl)-4,5-dihydropyridazin-3(2H)-ones as potential positive inotropic agents. Egypt. J. Pharm. Sci., 1998, 38, 319-331.
[62]
Abouzid, K.; Abdel Hakeem, M.; Khalil, O.; Maklad, Y. Pyridazinone derivatives: Design, synthesis, and in vitro vasorelaxant activity. Bioorg. Med. Chem., 2008, 16(1), 382-389.
[http://dx.doi.org/10.1016/j.bmc.2007.09.031] [PMID: 17905589]
[63]
Curran, W.V.; Ross, A. 6-Phenyl-4,5-dihydro-3(2H)-pyridazinones. A series of hypotensive agents. J. Med. Chem., 1974, 17(3), 273-281.
[http://dx.doi.org/10.1021/jm00249a004] [PMID: 4204335]
[64]
Weishaar, R.E.; Quade, M.M.; Schenden, J.A.; Evans, D.B. Relationship between inhibition of cardiac muscle phosphodiesterases, changes in cyclic nucleotide levels, and contractile response for CI-914 and other novel cardiotonics. J. Cyclic Nucleotide Protein Phosphor. Res., 1985, 10(6), 551-564.
[PMID: 3003170]
[65]
Lee, S.G.; Kim, J.J.; Kweon, D.H.; Kang, Y.J.; Cho, S.D.; Kim, S.K.; Yoon, Y.J. Recent progress in pyridazin-3(2H)ones chemistry. Curr. Med. Chem., 2004, 8, 1463-1480.
[66]
Kithas, P.A.; Artman, M.; Thompson, W.J.; Strada, S.J. Activity in rabbit ventricular myocardium: Relations to the effects of cardiotonic Subcellular distribution of high-affinity type IV cyclic AMP phosphodiesterase drugs. J. Am. Heart Asso. Circ. Res., 1988, 62, 782-789.
[http://dx.doi.org/10.1161/01.RES.62.4.782] [PMID: 2832097]
[67]
Felix, R.M.; Dario, E.; Lorena, B.; Isabel, R.I.E.; Juan, C.G.; Javier, D.M.; Juan, P.U. The vasodilatory effects of evosimendan on the human internal mammary artery. Inter. Anesthesia. Res. Soc., 2006, 103(5), 1094-1098.
[68]
Verdouw, P.D.; Hartog, J.M.; Duncker, D.J.; Roth, W.; Saxena, P.R. Cardiovascular profile of pimobendan, a benzimidazole-pyridazinone derivative with vasodilating and inotropic properties. Eur. J. Pharmacol., 1986, 126(1-2), 21-30.
[http://dx.doi.org/10.1016/0014-2999(86)90733-8] [PMID: 2875884]
[69]
van der Giessen, W.J.; van Woerkens, L.J.; Duncker, D.J.; Roelandt, J.R.; Verdouw, P.D. Acute hemodynamic effects of nisoldipine and pimobendan in conscious pigs with chronic heart failure. J. Cardiovasc. Pharmacol., 1989, 14(4), 653-658.
[http://dx.doi.org/10.1097/00005344-198910000-00019] [PMID: 2478781]
[70]
Kubo, S.H. Effects of pimobendan on exercise tolerance and quality of life in patients with heart failure. Cardiology, 1997, 88(2)(Suppl. 2), 21-27.
[http://dx.doi.org/10.1159/000177481] [PMID: 9142432]
[71]
Pahernik, S.A.; Schmid, J.; Sauter, T.; Schildberg, F.W.; Koebe, H.G. Metabolism of pimobendan in long-term human hepatocyte culture: In vivo-in vitro comparison. Xenobiotica, 1995, 25(8), 811-823.
[http://dx.doi.org/10.3109/00498259509061896] [PMID: 8779223]
[72]
Kitada, Y.; Morita, M.; Narimatsu, A. Comparison of the effects of MCI-154, a new cardiotonic agent, and some Ca2+-sensitizing agents on the response of the contractile system to Ca2+ in skinned cardiac muscle. Jpn. J. Pharmacol., 1989, 50(4), 411-419.
[http://dx.doi.org/10.1016/S0021-5198(19)42424-4] [PMID: 2789299]
[73]
Korvald, C.; Nordhaug, D.O.; Steensrud, T.; Aghajani, E.; Myrmel, T. Vasodilation and mechanoenergetic inefficiency dominates the effect of the “Ca(2+)-sensitizer” MCI-154 in intact pigs. Scand. Cardiovasc. J., 2002, 36(3), 172-179.
[74]
Schneider, P.; Güttner, J.; Eckenfels, A.; Heinzel, G.; von Nicolai, H.; Trieb, G.; Lehmann, H. Comparative cardiac toxicity of the i.v. administered benzimidazole pyridazinon derivative Pimobendan and its enantiomers in female Beagle dogs. Exp. Toxicol. Pathol., 1997, 49(3-4), 217-224.
[http://dx.doi.org/10.1016/S0940-2993(97)80013-9] [PMID: 9314056]
[75]
Kumar, D.; Carron, R.; La Calle, C.D.; Jindal, D.P.; Bansal, R. Synthesis and evaluation of 2-substituted-6-phenyl-4,5-dihydropyridazin-3(2H)-ones as potent inodilators. Acta Pharm., 2008, 58(4), 393-405.
[http://dx.doi.org/10.2478/v1007-008-0021-4] [PMID: 19103574]
[76]
Seki, T.; Nakao, T.; Masuda, T.; Hasumi, K.; Gotanda, K.; Ishimori, T.; Honma, S.; Minami, N.; Shibata, K.; Yasuda, K. Studies on agents with vasodilator and beta-blocking activities. IV. Chem. Pharm. Bull. (Tokyo), 1996, 44(11), 2061-2069.
[http://dx.doi.org/10.1248/cpb.44.2061] [PMID: 8945771]
[77]
Wang, T.; Dong, Y.; Wang, L.C.; Xiang, B.R.; Chen, Z.; Qu, L.B. Design, synthesis and structure-activity relationship studies of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives as cardiotonic agents. Arzneimittelforschung, 2008, 58(11), 569-573.
[PMID: 19137907]
[78]
Bansal, R.; Kumar, D.; Carron, R.; de la Calle, C. Synthesis and vasodilatory activity of some amide derivatives of 6-(4-carboxymethyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone. Eur. J. Med. Chem., 2009, 44(11), 4441-4447.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.006] [PMID: 19589624]
[79]
Demirayak, S.; Karaburun, A.C.; Beis, R. Some pyrrole substituted aryl pyridazinone and phthalazinone derivatives and their antihypertensive activities. Eur. J. Med. Chem., 2004, 39(12), 1089-1095.
[http://dx.doi.org/10.1016/j.ejmech.2004.09.005] [PMID: 15571871]
[80]
Yalamanchili, P.; Wexler, E.; Hayes, M.; Yu, M.; Bozek, J.; Kagan, M.; Radeke, H.S.; Azure, M.; Purohit, A.; Casebier, D.S.; Robinson, S.P. Mechanism of uptake and retention of F-18 BMS-747158-02 in cardiomyocytes: A novel PET myocardial imaging agent. J. Nucl. Cardiol., 2007, 14(6), 782-788.
[http://dx.doi.org/10.1016/j.nuclcard.2007.07.009] [PMID: 18022104]
[81]
Azzolina, O.; Dal Piaz, V.; Collina, S.; Giovannoni, M.P.; Tadini, C. Chiral resolution and absolute configuration of the enantiomers of 5-acetyl-2-methyl-4-methylsulfinyl-6-phenyl-3(2H)-pyridazinone and evaluation of their platelet aggregation inhibitory activity. Chirality, 1997, 9(7), 681-685.
[http://dx.doi.org/10.1002/(SICI)1520-636X(1997)9:7<681:AID-CHIR8>3.0.CO;2-A] [PMID: 9366028]
[82]
Mikashima, H.; Nakao, T.; Goto, K.; Ochi, H.; Yasuda, H.; Tsumagari, T. Y-590 (a new pyridazinone derivative), a potent anti-thrombotic agent--II. Inhibition of platelet phosphodiesterase. Thromb. Res., 1984, 35(5), 589-594.
[http://dx.doi.org/10.1016/0049-3848(84)90291-3] [PMID: 6091293]
[83]
Zeng, G.Q.; Wang, X.S.; Sun, D.X.; Lin, A.Y.; Ji, Y.; Chu, J.X.; Rui, Y.C. Effects of 6-(alpha alpha-diphenylacetylpiperazinyl) phenyl-5-methyl-4,5-dihydro-3(2H)-pyridazinone on rabbit platelet aggregation and TXB2, cAMP production. Yao Xue Xue Bao, 1993, 28(4), 256-259.
[84]
Pham, H.C.; Lasserre, B.; Pham, H.C.A. Palhares de, M.A.L.; Tronche, P.; Couquelet, J.; Rubat, C. A selective inhibitor of thromboxane synthetase activity of rabbit heart tissue: A pyridazinic derivative. Prostag. Leukot. Essen. Prostaglandins Leukot. Essent. Fatty Acids, 1988, 33(2), 143-147.
[http://dx.doi.org/10.1016/0952-3278(88)90154-8]
[85]
Cherng, S.C.; Huang, W.H.; Shiau, C.Y.; Lee, A.R.; Chou, T.C. Mechanisms of antiplatelet activity of PC-09, a newly synthesized pyridazinone derivative. Eur. J. Pharmacol., 2006, 532(1-2), 32-37.
[http://dx.doi.org/10.1016/j.ejphar.2005.12.022] [PMID: 16457809]
[86]
Salvi, K.; Bhambi, D.; Jat, J.L.; Ganpat, L. Talesara synthesis and antimicrobial activity of some 2-[1-(4-oxo-3,4-dihydrophthalazine-1-yl)alkyl]-1H-isoindole-1,3(2h)-dione and their imidoxy derivatives. ARKIVOC, 2006, 14, 133-140.
[87]
Xia-Juan, Z.; Gui-Yu, J. Synthesis of pyridazinonethiadiazoles as possible antifungal agents. Chin. Chem. Lett., 2001, 12(5), 419-420.
[88]
Xia-Juan, Z.; Lu-Hua, L.A.I.; Gui-Yu, J.I.N.; Zu-Xing, Z. Anti microbial synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted-1,3,4-oxadiazoles and 1,3,4-thiadiazoles. J. Agric. Food Chem., 2002, 50(13), 3757-3760.
[http://dx.doi.org/10.1021/jf0201677] [PMID: 12059155]
[89]
Sayed, G.H.; Hamed, A.A.; Meligi, G.A.; Boraie, W.E.; Shafik, M. The use of 4-(3,4-dichlorophenyl)-4-oxo-2-(4-antipyrinyl)-butanoic acid in the preparation of some new heterocyclic compounds with expected biological activity. Molecules, 2003, 8(3), 322-332.
[http://dx.doi.org/10.3390/80300322]
[90]
Sönmez, M.; Berber, I. Akbaş E. Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes. Eur. J. Med. Chem., 2006, 41(1), 101-105.
[http://dx.doi.org/10.1016/j.ejmech.2005.10.003] [PMID: 16293349]
[91]
Ashraf, A.F.W.; Mohamed, M.H.A.; Mahassen, S.A.; Shafey, G.D.; Aly, A.A. γ-Oxo Carboxylic Acids in Heterocyclic Synthesis, III. Synthesis of biologically active 4-Benzylamino-6-(5,5-dioxodibenzothiophen-2-yl)-2,3,4,5-tetrahydropyridazin-3-ones; Verlag der Zeitschrift fur Naturforschung, 2001, pp. 669-676.
[92]
Suree, N.; Yi, S.W.; Thieu, W.; Marohn, M.; Damoiseaux, R.; Chan, A.; Jung, M.E.; Clubb, R.T. Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors. Bioorg. Med. Chem., 2009, 17(20), 7174-7185.
[http://dx.doi.org/10.1016/j.bmc.2009.08.067] [PMID: 19781950]
[93]
Bambury, R.E.; Feeley, D.T.; Lawton, G.C.; Weaver, J.M.; Wemple, J. Mesoionic pyridazine ribonucleosides. A novel biologically active nucleoside metabolite. J. Med. Chem., 1984, 27(12), 1613-1621.
[94]
Jeremy, R.G.; Graziano, N.; Hugh, R.C.; Kenneth, M.; Robin, D.A.; Graham, A.R.J. Theoretical studies on the free-radical bromination of methyl-pyridazines in the synthesis of novel heterocyclic analogues of neurotransmitters. J. Mol. Struct. THEOCHEM, 1996, 368, 235-243.
[http://dx.doi.org/10.1016/S0166-1280(96)90569-2]
[95]
Coudert, P.; Duroux, E.; Bastide, P.; Couquelet, J.; Tronche, P. [Synthesis and evaluation of the aldose reductase inhibitory activity of new diaryl pyridazine-3-ones]. J. Pharm. Belg., 1991, 46(6), 375-380.
[PMID: 1783971]
[96]
Sato, M. [Pharmacological studies of 4-ethoxy-2-methyl-5- morpholino-3(2H)-pyridazinone (M73101). (5) Action of M73101 on the central nervous system (author’s transl)]. Nippon Yakurigaku Zasshi, 1979, 75(7), 695-706.
[http://dx.doi.org/10.1254/fpj.75.695] [PMID: 575516]
[97]
Fuks, B.; Talaga, P.; Huart, C.; Hénichart, J.P.; Bertrand, K.; Grimée, R.; Lorent, G. In vitro properties of 5-(benzylsulfonyl)-4-bromo-2-methyl-3(2H)-pyridazinone: A novel permeability transition pore inhibitor. Eur. J. Pharmacol., 2005, 519(1-2), 24-30.
[http://dx.doi.org/10.1016/j.ejphar.2005.06.046] [PMID: 16099453]
[98]
Betti, L.; Zanelli, M.; Giannaccini, G.; Manetti, F.; Schenone, S.; Strappaghetti, G. Synthesis of new piperazine-pyridazinone derivatives and their binding affinity toward alpha1-, alpha2-adrenergic and 5-HT1A serotoninergic receptors. Bioorg. Med. Chem., 2006, 14(8), 2828-2836.
[http://dx.doi.org/10.1016/j.bmc.2005.12.009] [PMID: 16376083]
[99]
Allerton, C.M.; Andrews, M.D.; Blagg, J.; Ellis, D.; Evrard, E.; Green, M.P.; Liu, K.K.; McMurray, G.; Ralph, M.; Sanderson, V.; Ward, R.; Watson, L. Design and synthesis of pyridazinone-based 5-HT(2C) agonists. Bioorg. Med. Chem. Lett., 2009, 19(19), 5791-5795.
[http://dx.doi.org/10.1016/j.bmcl.2009.07.136] [PMID: 19716297]
[100]
Banarjee, P.S.; Sharma, P.K.; Nema, R.K. Synthesis and anticonvulsant activity of pyridazinone derivatives. Inter. J. Chem. Tech. Res., 2009, 1(3), 522-525.
[101]
Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J.T. Synthesis and anticonvulsant activity of novel 1-substituted-1,2-dihydro-pyridazine-3,6-diones. Biol. Pharm. Bull., 2003, 26(10), 1407-1411.
[http://dx.doi.org/10.1248/bpb.26.1407] [PMID: 14519945]
[102]
Xu, P.; Wang, S.Y.; Liu, W.Q. Studies on synthesis and anticonvulsant activity of 3-GABA derivatives of 6-(substituted-phenyl) pyridazines. Yao Xue Xue Bao, 1991, 26(9), 650-655.
[PMID: 1821083]
[103]
Hallot, A.; Brodin, R.; Merlier, J.; Brochard, J.; Chambon, J.P.; Biziere, K. Synthesis and activity of 6-aryl-3-(hydroxypolymethyleneamino)pyridazines in animal models of epilepsy. J. Med. Chem., 1986, 29(3), 369-375.
[http://dx.doi.org/10.1021/jm00153a011] [PMID: 3950916]
[104]
Perio, A.; Chambon, J.P.; Calassi, R.; Heaulme, M.; Biziere, K. Evaluation of two anticonvulsant amino-pyridazine derivatives in the conflict test in rats. J. Pharmacol. Exp. Ther., 1986, 239(2), 542-547.
[PMID: 3095540]
[105]
Rakib, E.M.; Abouricha, S.; Hannioui, A.; Benchat, N.; Ait M’Barek, L.; Zyad, A. Synthesis and in vitro cytotoxicity studies of novel triazolo[4,3-b]pyridazinones. J. Iran. Chem. Soc., 2006, 3(3), 272-276.
[http://dx.doi.org/10.1007/BF03247219]
[106]
Meijer, L.; Flajolet, M.; Greengard, P. Pharmacological inhibitors of glycogen synthase kinase 3. Trends Pharmacol. Sci., 2004, 25(9), 471-480.
[http://dx.doi.org/10.1016/j.tips.2004.07.006] [PMID: 15559249]
[107]
Haider, N.; Sotelo, E. 1,5-dimethyl-6H-pyridazino[4,5-b]carbazole, a 3-aza bioisoster of the antitumor alkaloid olivacine. Chem. Pharm. Bull. (Tokyo), 2002, 50(11), 1479-1483.
[http://dx.doi.org/10.1248/cpb.50.1479] [PMID: 12419913]
[108]
Malinka, W.; Redzicka, A.; Lozach, O. New derivatives of pyrrolo[3,4-d]pyridazinone and their anticancer effects. Farmaco, 2004, 59(6), 457-462.
[http://dx.doi.org/10.1016/j.farmac.2004.03.002] [PMID: 15178308]
[109]
Cao, S.; Qian, X.; Song, G.; Chai, B.; Jiang, Z. Synthesis and antifeedant activity of new oxadiazolyl 3(2H)-pyridazinones. J. Agric. Food Chem., 2003, 51(1), 152-155.
[http://dx.doi.org/10.1021/jf0208029] [PMID: 12502400]
[110]
Nagai, H.; Suda, H.; Iwama, T.; Daikoku, M.; Yanagihara, Y.; Koda, A. Effect of NZ-107, a newly synthesized pyridazinone derivative, on antigen-induced contraction of human bronchial strips and histamine release from human lung fragments or leukocytes. Int. Arch. Allergy Immunol., 1992, 98(1), 57-63.
[http://dx.doi.org/10.1159/000236164] [PMID: 1378042]
[111]
Hibi, M.; Shikada, K.; Iwama, T.; Yamamoto, A.; Sakashita, M.; Tanaka, S. Inhibitory effect of the newly synthesized pyridazinone derivative NZ-107 on bronchoconstriction induced by slow reacting substance of anaphylaxis in the guinea pig. Jpn. J. Pharmacol., 1989, 51(3), 411-419.
[http://dx.doi.org/10.1016/S0021-5198(19)40102-9] [PMID: 2622094]
[112]
Huang, Q.; Kong, Y.; Liu, M.; Feng, J.; Liu, Y. Effect of oxadiazolyl 3(2H)-pyridazinone on the larval growth and digestive physiology of the armyworm, Pseudaletia separata. J. Insect Sci., 2008, 8(19), 19.
[http://dx.doi.org/10.1673/031.008.1901] [PMID: 20337556]
[113]
Abdelrazek, F.M.; Michael, F.A.; Mohamed, A.E. Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3-d]thiazole derivatives. Arch. Pharm. (Weinheim), 2006, 339(6), 305-312.
[http://dx.doi.org/10.1002/ardp.200500259] [PMID: 16649159]
[114]
Xu, H.; Zou, X.M.; Zhu, Y.Q.; Liu, B.; Tao, H.L.; Hu, X.H.; Song, H.B.; Hu, F.Z.; Wang, Y.; Yang, H.Z. Synthesis and herbicidal activity of novel alpha,alpha,alpha-trifluoro-m-tolyl pyridazinone derivatives. Pest Manag. Sci., 2006, 62(6), 522-530.
[http://dx.doi.org/10.1002/ps.1195] [PMID: 16602079]
[115]
Rathish, I.G.; Javed, K.; Bano, S.; Ahmad, S.; Alam, M.S.; Pillai, K.K. Synthesis and blood glucose lowering effect of novel pyridazinone substituted benzenesulfonylurea derivatives. Eur. J. Med. Chem., 2009, 44(6), 2673-2678.
[http://dx.doi.org/10.1016/j.ejmech.2008.12.013] [PMID: 19171410]
[116]
Yuefen, Z.; Lian, S.L.; Peter, S.D.; Douglas, E.M.; Chinh, V.T.; Frank, R.; Stephen, E.W.; Amit, M.S.; Mei, T.; April, A.; Richard, E.S.; Rupal, P.; Qing, H.; Qiang, Z.; Thomas, H.; Charles, R.K.; Laurie, L.; Maria, V.S. Novel HCV NS5B polymerase inhibitors derived from 4-(10,10-dioxo-10,40-dihydro-10k6-benzo[10,20,40] thiadiazin-30-yl)-5-hydroxy-2H-pyridazin-3-ones. Part 2: Variation of the 2- and 6-pyridazinone substituents. Bioorg. Med. Chem. Lett., 2008, 18, 1419-1424.
[http://dx.doi.org/10.1016/j.bmcl.2008.01.005] [PMID: 18226901]
[117]
Youssef, A.S.A.; Marzouk, M.I.; Madkour, H.M.F.A.; El-Soll, M.A.; El-Hashash, M.A. Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-yl-pyridazin-3-one. Can. J. Chem., 2005, 83(3), 251-259.
[http://dx.doi.org/10.1139/v05-045]
[118]
Heinisch, G.; Frank, H. Pharmacologically active pyridazine derivatives. Part 1. Prog. Med. Chem., 1990, 27, 1-49.
[http://dx.doi.org/10.1016/S0079-6468(08)70288-1] [PMID: 2217822]
[119]
Hovakimyan, S.A.; Babakhanyan, A.; Voskanyan, S.; Karapetian, E.; Panosyan, G.A.; Kocharian, S.T. Synthesis of pyridazinone derivatives. Chem. Heterocycl. Compd., 2004, 40(8), 8.
[http://dx.doi.org/10.1023/B:COHC.0000046696.37815.62]
[120]
Archan, S.; Toller, W. Levosimendan: Current status and future prospects. Curr. Opin. Anaesthesiol., 2008, 21(1), 78-84.
[http://dx.doi.org/10.1097/ACO.0b013e3282f357a5] [PMID: 18195615]
[121]
Sircar, I.; Morrison, G.C.; Burke, S.E.; Skeean, R.; Weishaar, R.E. Cardiotonic agents. 6. Synthesis and inotropic activity of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones: Ring-contracted analogues of imazodan (CI-914). J. Med. Chem., 1987, 30(10), 1724-1728.
[http://dx.doi.org/10.1021/jm00393a007] [PMID: 3656349]
[122]
Ishimori, T.; Gotanda, K.; Sasaki, T.; Shinbo, A.; Asano, H.; Miyazawa, K.; Miyasaka, K. Cardiac effects of the novel pyridazinone derivative 6-[4-[2-[3-(5-chloro-2-cyanophenoxy)-2-hydroxypropylamino]- 2- methylpropylamino]phenyl]-4,5-dihydro-5-methyl-3(2H) pyridazinone monoethyl maleate and its metabolite in isolated heart preparations of guinea pigs and dogs. Arzneimittelforschung, 1994, 44(5), 583-588.
[PMID: 7912931]
[123]
Araki, S.; Uematsu, T.; Nagashima, S.; Matsuzaki, T.; Gotanda, K.; Ochiai, H.; Hashimoto, H.; Nakashima, M. Cardiac and hemodynamic effects of TZC-5665, a novel pyridazinone derivative, and its metabolite in humans and dogs. Gen. Pharmacol., 1997, 28(4), 545-553.
[http://dx.doi.org/10.1016/S0306-3623(96)00302-3] [PMID: 9147023]
[124]
Uhlmann, R.; Schwinger, R.H.; Lues, I.; Erdmann, E. EMD 53998 acts as Ca(2+)-sensitizer and phosphodiesterase III-inhibitor in human myocardium. Basic Res. Cardiol., 1995, 90(5), 365-371.
[http://dx.doi.org/10.1007/BF00788497] [PMID: 8585857]
[125]
Bowman, P.; Haikala, H.; Paul, R.J. Levosimendan, a calcium sensitizer in cardiac muscle, induces relaxation in coronary smooth muscle through calcium desensitization. J. Pharmacol. Exp. Ther., 1999, 8(1), 316-325.
[126]
Chen, H.Z.; Cui, X.L.; Zhao, H.C.; Zhao, L.Y.; Lu, J.Y.; Wu, B.W. Inotropic effects of MCI-154 on rat cardiac myocytes. Sheng Li Xue Bao, 2004, 56(3), 301-305.
[PMID: 15224141]
[127]
Iwamoto, H. Effect of a cardiotonic agent, MCI-154, on the contractile properties of skinned skeletal muscle fibers. Eur. J. Pharmacol., 1998, 341(2-3), 243-252.
[http://dx.doi.org/10.1016/S0014-2999(97)01469-6] [PMID: 9543245]
[128]
Schudt, C.; Winder, S.; Müller, B.; Ukena, D. Zardaverine as a selective inhibitor of phosphodiesterase isozymes. Biochem. Pharmacol., 1991, 42(1), 153-162.
[http://dx.doi.org/10.1016/0006-2952(91)90694-Z] [PMID: 1648920]
[129]
Sotelo, E.; Coelho, A.; Raviña, E. Pyridazine derivatives 32: Stille-based approaches in the synthesis of 5-substituted-6-phenyl-3(2H)-pyridazinones. Chem. Pharm. Bull. (Tokyo), 2003, 51(4), 427-430.
[http://dx.doi.org/10.1248/cpb.51.427] [PMID: 12672999]
[130]
Rüegg, J.C.; Pfitzer, G.; Eubler, D.; Zeugner, C. Effect on contractility of skinned fibres from mammalian heart and smooth muscle by a new benzimidazole derivative, 4,5-dihydro-6-[2-(4-methoxyphenyl)-1H-benzimidazol-5-yl]-5-methy l-3(2H)- pyridazinone. Arzneimittelforschung, 1984, 34(12), 1736-1738.
[PMID: 6543308]
[131]
Sivakumar, R.; Kishore Gnanasam, S.; Ramachandran, S.; Leonard, J.T. Pharmacological evaluation of some new 1-substituted-4-hydroxy-phthalazines. Eur. J. Med. Chem., 2002, 37(10), 793-801.
[http://dx.doi.org/10.1016/S0223-5234(02)01405-8] [PMID: 12446037]
[132]
Takaya, M.; Sato, M.; Terashima, K.; Tanizawa, H.; Maki, Y. A new nonsteroidal analgesic-antiinflammatory agent. Synthesis and activity of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone and related compounds. J. Med. Chem., 1979, 22(1), 53-58.
[http://dx.doi.org/10.1021/jm00187a013] [PMID: 311385]
[133]
Chintakunta, V.K.; Akella, V.; Vedula, M.S.; Mamnoor, P.K.; Mishra, P.; Casturi, S.R.; Vangoori, A.; Rajagopalan, R. 3-O-substituted benzyl pyridazinone derivatives as COX inhibitors. Eur. J. Med. Chem., 2002, 37(4), 339-347.
[http://dx.doi.org/10.1016/S0223-5234(02)01336-3] [PMID: 11960669]
[134]
Asif, M. Some recent approaches of biologically active substituted pyridazine and phthalazine drugs. Curr. Med. Chem., 2012, 19(18), 2984-2991.
[http://dx.doi.org/10.2174/092986712800672139] [PMID: 22519394]
[135]
Asif, M. Antifeedant, herbicidal and molluscicidal activities of pyridazinone compounds. Mini Rev. Org. Chem., 2013, 10(2), 113-122.
[http://dx.doi.org/10.2174/1570193X11310020002]
[136]
Asif, M.; Singh, A.; Bilkanti, L. In-vivo anticonvulsant and in-vitro antitubercular activity of methyl indole derivative of some 6-aryl-4, 5dihydropyridazin-3-(2H)-ones and their expected anticonvulsant mechanisms. Iran. J. Pharm. Res., 2013, 9(1), 67-80.
[137]
Rubat, C.; Coudert, P.; Refouvelet, B.; Tronche, P.; Bastide, P.; Bastide, J. Anticonvulsant activity of 3-oxo-5-substituted benzylidene-6-methyl-(4H)-2-pyridazinylacetamides and 2-pyridazinylacetylhydrazides. Chem. Pharm. Bull. (Tokyo), 1990, 38(11), 3009-3013.
[http://dx.doi.org/10.1248/cpb.38.3009] [PMID: 2128224]
[138]
Tan, O.Ü.; Özadali, K. Yeşilyurt, Ö.; Kayir, H.; Uzbay, İT.; Balkan, A. Synthesis and evaluation of the analgesic activity of some new isoxazolo[4,5-d]pyridazin-4(5H)-one derivatives. Turk. J. Chem., 2011, 35, 121-130.
[139]
Moreau, S.; Coudert, P.; Rubat, C.; Vallee-Goyet, D.; Gardette, D.; Gramain, J.C.; Couquelet, J. Synthesis and anticonvulsant properties of triazolo- and imidazopyridazinyl carboxamides and carboxylic acids. Bioorg. Med. Chem., 1998, 6(7), 983-991.
[http://dx.doi.org/10.1016/S0968-0896(98)00057-1] [PMID: 9730234]
[140]
Chopin, P.; Assié, M.B.; Briley, M. Neuropharmacology of a new potential anxiolytic compound, F 2692, 1-(3′-trifluoromethyl phenyl) 1, 4-dihydro 3-amino 4-oxo 6-methyl pyridazine. 2. Evaluation of its tolerance and dependence producing potential and of its effects on benzodiazepine withdrawal in the elevated plus-maze test in rats. Psychopharmacology (Berl.), 1993, 110(1-2), 19-26.
[http://dx.doi.org/10.1007/BF02246946] [PMID: 7870883]
[141]
Assié, M.B.; Chopin, P.; Stenger, A.; Palmier, C.; Briley, M. Neuropharmacology of a new potential anxiolytic compound, F 2692, 1-(3′-trifluoromethyl phenyl) 1,4-dihydro 3-amino 4-oxo 6-methyl pyridazine. 1. Acute and in vitro effects. Psychopharmacology (Berl.), 1993, 110(1-2), 13-18.
[http://dx.doi.org/10.1007/BF02246945] [PMID: 7870872]
[142]
Schaffler, K.; Wauschkuhn, C.H.; Gierend, M. Analgesic potency of a new anticonvulsant drug versus acetylsalicylic acid via laser somatosensory evoked potentials. Randomized placebo-controlled double-blind (5-way) crossover study. Arzneimittelforschung, 1991, 41(4), 427-435.
[PMID: 1859518]
[143]
Santucci, V.; Rocher, D.; Veyrun, J.; Bizière, K. Quantitative electroencephalographic profile of 3-(4-hydroxy-1-piperidinyl)-6-(2,4-dichlorophenyl)-pyridazine (SR 41378) in the rat. Naunyn Schmiedebergs Arch. Pharmacol., 1986, 333(2), 186-189.
[http://dx.doi.org/10.1007/BF00506525] [PMID: 2875399]
[144]
Chambon, J.P.; Brochard, J.; Hallot, A.; Heaulme, M.; Brodin, R.; Roncucci, R.; Biziere, K. CM 40907: A structurally novel anticonvulsant in mice, rats and baboons. J. Pharmacol. Exp. Ther., 1985, 233(3), 836-844.
[PMID: 2989499]
[145]
Nakao, T.; Kawakami, M.; Morita, K.; Obata, M.; Morimoto, Y.; Takehara, S.; Tahara, T. [Studies on the synthesis of condensed pyridazine derivatives. II. Synthesis and anxiolytic activities of 2-aryl-4,4a,5,6-tetrahydropyridazino[4,3-c]quinolin-3(2H)-ones, 2-aryl-4a,5-dihydro-2H-(1)benzothiopyrano[4,3-c]pyridazin-3(4H)-ones, and related compounds] Yakugaku Zasshi, 1990, 110(8), 573-585.
[http://dx.doi.org/10.1248/yakushi1947.110.8_573] [PMID: 1980306]
[146]
Zabska, R. Kołodziejczyk, A.; Sieklucka-Dziuba, M.; Morawska, D.; Kleinrok, Z. Synthesis and pharmacological screening of pyrazolo[3,4-c]pyridazine derivatives. Acta Pol. Pharm., 1998, 55(4), 305-310.
[PMID: 9821396]
[147]
Altomare, C.; Campagna, F.; Carta, V.; Cellamare, S.; Carotti, A.; Genchi, G.; De Sarro, G. Synthesis, benzodiazepine receptor affinity and anticonvulsant activity of 5-H-indeno[1,2-c]pyridazine derivatives. Farmaco, 1994, 49(5), 313-323.
[PMID: 8080613]
[148]
Griebel, G.; Perrault, G.; Tan, S.; Schoemaker, H.; Sanger, D.J. Comparison of the pharmacological properties of classical and novel BZ-omega receptor ligands. Behav. Pharmacol., 1999, 10(5), 483-495.
[http://dx.doi.org/10.1097/00008877-199909000-00007] [PMID: 10780255]
[149]
Gobnitzer, E.; Krbavcic, A.; Wendelin, W.; Krbavcic, M. Synthesis and structure investigations of potential sedative and anticonvulsant hydroxy- and acetoxy-N-(3-oxobutyl)-pyrido[2,3-d]pyridazinones. Monatsh. Chem., 2002, 133(9), 1177-1185.
[http://dx.doi.org/10.1007/s00706-002-0473-z]
[150]
Said, M.M.; Ahmed, A.A.E.; El-Alfy, A.T. Synthesis and pharmacological screening for muscle relaxant, anticonvulsant, and sedative activities of certain organic compounds produced by Michael addition. Arch. Pharm. Res., 2004, 27(12), 1194-1201.
[http://dx.doi.org/10.1007/BF02975880] [PMID: 15646790]
[151]
Faidallah, H.M.; Khan, K.A.; Makki, M.S.I. Synthesis and biological evaluation of new fused isoxazolo[4,5-d] pyridazine derivatives. J. Chin. Chem. Soc. (Taipei), 2011, 58(2), 191-198.
[http://dx.doi.org/10.1002/jccs.201190076]
[152]
Wright, A.; Bai, G.; Barrera, L.; Boulahbal, F.; Martin-Casabona, N.; Gilpin, C.; Drobniewski, F.; Havelková, M.; Lepe, R.; Lumb, R.; Metchock, B. Emergence of Mycobacterium tuberculosis with extensive resistance to second-line drugs-worldwide, 2000-2004. MMWR Morb. Mortal. Wkly. Rep., 2006, 55(11), 301-305.
[153]
Kamal, A.; Azeeza, S.; Malik, M.S.; Shaik, A.A.; Rao, M.V. Efforts towards the development of new antitubercular agents: Potential for thiolactomycin based compounds. J. Pharm. Pharm. Sci., 2008, 11(2), 56s-80s.
[http://dx.doi.org/10.18433/J36K5K] [PMID: 19203471]
[154]
Okada, M.; Kobayashi, K. [Recent progress in mycobacteriology]. Kekkaku, 2007, 82(10), 783-799.
[PMID: 18018602]
[155]
Tomioka, H.; Namba, K. Development of antituberculous drugs: Current status and future prospects. Kekkaku, 2006, 81(12), 753-774.
[PMID: 17240921]
[156]
Utku, S.; Gokce, M.; Aslan, G.; Bayram, G.; Ulger, M.; Emekdas, G.; Sahin, M.F. Synthesis and in vitro antimycobacterial activities of novel 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(substituted/nonsubstituted acetophenone)hydrazone. Turk. J. Chem., 2001, 35, 331-339.
[157]
Husain, A.; Ahmad, A.; Bhandari, A.; Ram, V. Synthesis and antitubercular activity of pyridazinone derivatives. J. Chil. Chem. Soc., 2011, 56(3), 778-780.
[http://dx.doi.org/10.4067/S0717-97072011000300013]
[158]
Dogruer, D.S.; Onkol, T.; Ozkan, S.; Ozgen, S.; Sahin, M.F. Synthesis and antimicrobial activity of some 3(2H)-pyridazinone and 1(2H)-phthalazinone derivatives. Turk. J. Chem., 2008, 32, 469-479.
[159]
Islam, M.; Siddiqui, A.A.; Rajesh, R. Synthesis, antitubercular, antifungal and antibacterial activities of 6-substituted phenyl-2-(3′-substituted phenyl pyridazin-6′-yl)-2,3,4,5-tetrahydropyridazin-3-one. Acta Pol. Pharm., 2008, 65(4), 441-447.
[PMID: 19051585]
[160]
Islam, M.; Siddiqui, A.A.; Rajesh, R.; Bakht, A.; Goel, S. Synthesis and antimicrobial activity of some novel oxadiazole derivatives. Acta Pol. Pharm., 2008, 65(3), 353-362.
[PMID: 18646555]
[161]
Japelj, B.; Recnik, S.; Cebasek, P.; Stanovnik, B.; Svete, J. Synthesis and antimycobacterial activity of alkyl 1-heteroaryl-1H-1,2,3-triazole-4-carboxylates. J. Heterocycl. Chem., 2005, 42(6), 1167-1173.
[http://dx.doi.org/10.1002/jhet.5570420620]
[162]
Velezheva, V.S.; Brennan, P.J.; Marshakov, V.Y.; Gusev, D.V.; Lisichkina, I.N.; Peregudov, A.S.; Tchernousova, L.N.; Smirnova, T.G.; Andreevskaya, S.N.; Medvedev, A.E. Novel pyridazino[4,3-b]indoles with dual inhibitory activity against Mycobacterium tuberculosis and monoamine oxidase. J. Med. Chem., 2004, 47(13), 3455-3461.
[http://dx.doi.org/10.1021/jm030479g] [PMID: 15189042]
[163]
Haider, N.; Kabicher, T.; Käferböck, J.; Plenk, A. Synthesis and in-vitro antitumor activity of 1-[3-(indol-1-yl)prop-1-yn-1-yl]phthalazines and related compounds. Molecules, 2007, 12(8), 1900-1909.
[http://dx.doi.org/10.3390/12081900] [PMID: 17960095]
[164]
Shetgiri, N.P.; Nayak, B.N. Synthesis and antimicrobial activities of oxadiazoles, phthalazines and indolinones. ChemInform, 2005, 44B(6), 1267-1272.
[http://dx.doi.org/10.1002/chin.200545041]
[165]
Nagawade, R.R.; Khanna, V.V.; Bhagwat, S.S.; Shinde, D.B. Synthesis of new series of 1-Aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents. Eur. J. Med. Chem., 2005, 40(12), 1325-1330.
[http://dx.doi.org/10.1016/j.ejmech.2005.05.012] [PMID: 16126308]
[166]
Park, E.H.; Park, M.S. Synthesis of potential anticancer 6-allylthio-3-aminopyridazine derivatives. J. Kor. Chem. Soc., 2007, 51(3), 244-250.
[http://dx.doi.org/10.5012/jkcs.2007.51.3.244]
[167]
Asif, M.; Singh, A.; Siddiqui, A.A. The effect of pyridazine compounds on the cardiovascular system. Med. Chem. Res., 2012, 21(11), 3336-3346.
[http://dx.doi.org/10.1007/s00044-011-9835-6]
[168]
Costas, T.; Besada, P.; Piras, A.; Acevedo, L.; Yañez, M.; Orallo, F.; Laguna, R.; Terán, C. New pyridazinone derivatives with vasorelaxant and platelet antiaggregatory activities. Bioorg. Med. Chem. Lett., 2010, 20(22), 6624-6627.
[http://dx.doi.org/10.1016/j.bmcl.2010.09.031] [PMID: 20880705]
[169]
Frolov, E.B.; Lakner, F.J.; Khvat, A.V.; Ivachtchenko, A.V. An efficient synthesis of novel 1,3-oxazolo[4,5-d]pyridazinones. Tetrahedron Lett., 2004, 45(24), 4693-4696.
[http://dx.doi.org/10.1016/j.tetlet.2004.04.093]
[170]
Husain, A.; Drabu, S.; Kumar, N.; Alam, M.M.; Ahmad, A. Synthesis and biological evaluation of some new pyridazinone derivatives. J. Enzyme Inhib. Med. Chem., 2011, 26(5), 742-748.
[http://dx.doi.org/10.3109/14756366.2010.548810] [PMID: 21271866]
[171]
Siddiqui, A.A.; Mishra, R.; Shaharyar, M. Synthesis, characterization and antihypertensive activity of pyridazinone derivatives. Eur. J. Med. Chem., 2010, 45(6), 2283-2290.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.003] [PMID: 20189270]
[172]
Wang, T.; Xiang, B.; Wang, Y.; Chen, C.; Dong, Y.; Fang, H.; Wang, M. Spectroscopic investigation on the binding of bioactive pyridazinone derivative to human serum albumin and molecular modeling. Colloids Surf. B Biointerfaces, 2008, 65(1), 113-119.
[http://dx.doi.org/10.1016/j.colsurfb.2008.03.008] [PMID: 18456467]
[173]
Zhou, G.; Ting, P.C.; Aslanian, R.; Cao, J.; Kim, D.W.; Kuang, R.; Lee, J.F.; Schwerdt, J.; Wu, H.; Herr, R.J.; Zych, A.J.; Yang, J.; Lam, S.; Wainhaus, S.; Black, T.A.; McNicholas, P.M.; Xu, Y.; Walker, S.S. SAR studies of pyridazinone derivatives as novel glucan synthase inhibitors. Bioorg. Med. Chem. Lett., 2011, 21(10), 2890-2893.
[http://dx.doi.org/10.1016/j.bmcl.2011.03.083] [PMID: 21489787]
[174]
Imran, M.; Asif, M. Study of various pyridazine and phthalazine drugs with diverse therapeutical and agrochemical activities. Russ. J. Bioorganic Chem., 2020, 46(5), 745-767.
[http://dx.doi.org/10.1134/S1068162020050167]
[175]
Abouzid, K.; Khalil, N.; Ahmed, E.; Esmat, A.; Al-Abd, A. Design, synthesis, and evaluation of anti-inflammatory and ulcerogenicity of novel pyridazinone derivatives. Med. Chem. Res., 2012, 21(11), 3581-3590.
[http://dx.doi.org/10.1007/s00044-011-9895-7]
[176]
Özdemir, Z.; Gökçe, M.; Karakurt, A. Synthesis and analgesic antiinflammatory and antimicrobial evaluation of 6 substituted 3(2H)pyridazinone 2 acetyl 2 substituted benzal hydrazone derivatives. FABAD J. Pharm. Sci., 2012, 37, 111-122.
[177]
Saeed, M.M.; Khalil, N.A.; Ahmed, E.M.; Eissa, K.I. Synthesis and anti-inflammatory activity of novel pyridazine and pyridazinone derivatives as non-ulcerogenic agents. Arch. Pharm. Res., 2012, 35(12), 2077-2092.
[http://dx.doi.org/10.1007/s12272-012-1205-5] [PMID: 23263802]
[178]
Singh, A.; Asif, M. Analgesic and anti-inflammatory activities of several 4-substituted-6-(3′-nitrophenyl) pyridazin-(2H)-3-one derivatives. Brazil. J. Phram. Sci., 2013, 49(4), 903-909.
[179]
Rathish, I.G.; Javed, K.; Ahmad, S.; Bano, S.; Alam, M.S.; Akhter, M.; Pillai, K.K.; Ovais, S.; Samim, M. Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(p-sulfamylphenyl)-pyridazin-3(2H)-ones. Eur. J. Med. Chem., 2012, 49, 304-309.
[http://dx.doi.org/10.1016/j.ejmech.2012.01.026] [PMID: 22305543]
[180]
Sukuroglu, M.; Onkol, T. Onurdağ F.K.; Akalin, G.; Sahin, M.F. Synthesis and in vitro biological activity of new 4,6-disubstituted 3(2H)-pyridazinone-acetohydrazide derivatives. Z. Naturforsch. C, 2012, 67(5-6), 257-265.
[http://dx.doi.org/10.1515/znc-2012-5-604] [PMID: 22888530]

Rights & Permissions Print Cite
Article Metrics
109
2
Wayfinder Image
Open Access Journals Promotions
© 2024 Bentham Science Publishers | Privacy Policy