Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Mini-Review Article

Applications and Biological Potential of Substituted Pyridazine Analogs in Medicinal and Agricultural Fields

Author(s): Mohammad Asif*, Mamdouh Allahyani, Mazen Mohammed Almehmadi and Ahad Amer Alsaiari

Volume 27, Issue 10, 2023

Published on: 06 September, 2023

Page: [814 - 820] Pages: 7

DOI: 10.2174/1385272827666230809094221

Price: $65

Abstract

Pyridazine derivatives are an important heterocyclic family in medication development. Because of their biological relevance, there has been a surge in interest in the chemistry of pyridazine derivatives in recent years. Anti-tubercular, antifungal, antibacterial, analgesic, anti-inflammatory, antihypertensive, anticancer, antidiabetic, anti-AIDS, cardiovascular activity, anticonvulsant, and possibly useful neuroprotective actions have all been identified for pyridazine derivatives. They have also pesticide and herbicide action. The purpose of this study is to highlight the numerous pyridazine analogs as well as their pharmacological and agricultural implications.

Keywords: Heterocyclic, agriculture, biological activities, pyridazine, antibacterial, anti-tubercular.

Graphical Abstract
[1]
Asif, M.; Alghamdi, S. A mini-review on pyridazine analogs: Chemical and pharmacological potentials. Mini Rev. Org. Chem., 2023, 20(2), 100-123.
[http://dx.doi.org/10.2174/1570193X19666220329155551]
[2]
Yusuf, M.; Alsaiari, A.A.; Almehmadi, M.; Kamal, M.; Asif, M. In silico molecular studies and synthesis of some pyridazinone scaffolds as anti-proliferative agents. Indian J. Heterocycl. Chem., 2022, 32(03), 295-309.
[3]
Asif, M.; Singh, A. Synthesis and anti-tubercular activity of 6-] (4-chloro/methyl-phenyl)-4-arylidene-4,5-dihydropyridazin-3(2H)-one derivatives against Mycobacterium tuberculosis. Lett. Drug Des. Discov., 2015, 12(6), 500-504.
[http://dx.doi.org/10.2174/157018081206150507130832]
[4]
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]
[5]
Asif, M.; Singh, A.; Khan, S.A.; Husain, A. Studies on new substituted pyridazinones: Synthesis and biological evaluation. Braz. J. Pharm. Sci., 2018, 54(3), e00040.
[http://dx.doi.org/10.1590/s2175-97902018000300040]
[6]
Mohd, I.; Mohammad, A. 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]
[7]
Asif, M.; Imran, M. Antitubercular and anticonvulsant activities of phenyl-di-hydro-pyridazinone 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]
[8]
Mohd, A.; Mohammad, A. 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]
[9]
Özdemir, Z.; Utku, S.; Mathew, B.; Carradori, S.; Orlando, G.; Di Simone, S.; Alagöz, M.A.; Özçelik, A.B.; Uysal, M.; Ferrante, C. Synthesis and biological evaluation of new 3(2H)-pyridazinone derivatives as non-toxic anti-proliferative compounds against human colon carcinoma HCT116 cells. J. Enzyme Inhib. Med. Chem., 2020, 35(1), 1100-1109.
[http://dx.doi.org/10.1080/14756366.2020.1755670] [PMID: 32321320]
[10]
Asif, M.; Imran, M.; Kamal, M.; Acharya, M. Brine shrimp (Artemia salina) lethality bioassay of some 2-(alkyl/aryl)-6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives. Indian J. Heterocycl. Chem., 2021, 31, 57-61.
[11]
Asif, M.; Singh, A. Anticonvulsant Activities of 4-benzylidene-6-(4-methyl-phenyl)-4,5-dihydropyridazin-(2H)-ones and 4-benzylidene-6-(4-chloro-phenyl)-4,5-dihydropyridazin-(2H)-ones. Open Pharm. Sci. J., 2016, 3(1), 203-214.
[http://dx.doi.org/10.2174/1874844901603010196]
[12]
Asif, M.; Singh, A. Anticonvulsant activity of 4-(substituted benzylidene)-6-(3-nitrophenyl)-4,5-dihydro pyridazin-3(2H)-ones against maximal electroshock induced seizure. Middle East J. Sci. Res., 2011, 9, 481-485.
[13]
Asif, M.; Singh, A. Synthesis of new derivative of 2-[2-(1H-indol-1-yl)ethyl]-6-phenyl-4,5-dihydropyridazin-3(2H)-one. An. Univ. Ovidius Constanta Ser. Chim., 2011, 22, 98-101.
[14]
Asif, M.; Singh, D.; Singh, A. Analgesic activity of some 6-phenyl-4-substituted benzylidene tetrahydro pyridazin-3(2H)-ones. Glob. J. Pharmacol., 2011, 5, 18-22.
[15]
Asif, M.; Singh, A.; Lakshmayya, L. 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]
[16]
Asif, M. A mini review on biological activities of pyridazinone derivatives as antiulcer, antisecretory, antihistamine and particularly against histamine H3R. Mini Rev. Med. Chem., 2015, 14(13), 1093-1103.
[http://dx.doi.org/10.2174/1389557514666141127143133] [PMID: 25429662]
[17]
Asif, M. Overview on emorfazone and other related 3(2H) pyridazinone analogues displaying analgesic and anti-inflammatory activity. Ann. Med. Chem. Res., 2014, 1, 1004.
[18]
Asif, M.; Singh, A. Exploring potential, synthetic methods and general chemistry of pyridazine and pyridazinone: A brief introduction. Int. J. Chemtech Res., 2010, 2, 1112-1128.
[19]
Khan, A.; Diwan, A.; Thabet, H.K.; Imran, M.; Bakht, M.A. Discovery of novel pyridazine-based cyclooxygenase-2 inhibitors with a promising gastric safety profile. Molecules, 2020, 25(9), 2002.
[http://dx.doi.org/10.3390/molecules25092002] [PMID: 32344801]
[20]
Ahmad, S.; Rathish, I.G.; Bano, S.; Alam, M.S.; Javed, K. Synthesis and biological evaluation of some novel 6-aryl-2-(p-sulfamylphenyl)-4,5-dihydropyridazin-3(2H)-ones as anti-cancer, antimicrobial, and anti-inflammatory agents. J. Enzyme Inhib. Med. Chem., 2010, 25(2), 266-271.
[http://dx.doi.org/10.3109/14756360903155781] [PMID: 20038271]
[21]
Lattmann, E.; Ayuko, W.O.; Kinchinaton, D.; Langley, C.A.; Singh, H.; Karimi, L.; Tisdale, M.J. Synthesis and evaluation of 5-arylated 2(5H)-furanones and 2-arylated pyridazin-3(2H)-ones as anti-cancer agents. J. Pharm. Pharmacol., 2010, 55(9), 1259-1265.
[http://dx.doi.org/10.1211/0022357021756] [PMID: 14604469]
[22]
Murty, M.S.R.; Rao, B.R.; Ram, K.R.; Yadav, J.S.; Antony, J.; Anto, R.J. Synthesis and preliminary evaluation activity studies of novel 4-(aryl/heteroaryl-2-ylmethyl)-6-phenyl-2-[3-(4-substituted-piperazine-1-yl)propyl]pyridazin-3(2H)-one derivatives as anticancer agents. Med. Chem. Res., 2012, 21(10), 3161-3169.
[http://dx.doi.org/10.1007/s00044-011-9851-6]
[23]
Al-Tel, T.H. Design and synthesis of novel tetrahydro-2H-Pyrano[3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents. Eur. J. Med. Chem., 2010, 45(12), 5724-5731.
[http://dx.doi.org/10.1016/j.ejmech.2010.09.029] [PMID: 20884086]
[24]
Meade, E.A.; Wotring, L.L.; Drach, J.C.; Townsend, L.B. Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives. J. Med. Chem., 1993, 36(24), 3834-3842.
[http://dx.doi.org/10.1021/jm00076a011] [PMID: 8254613]
[25]
Özadalı K.; Özkanlı F.; Jain, S.; Rao, P.P.N.; Velázquez-Martínez, C.A. Synthesis and biological evaluation of isoxazolo[4,5-d]pyridazin-4-(5H)-one analogues as potent anti-inflammatory agents. Bioorg. Med. Chem., 2012, 20(9), 2912-2922.
[http://dx.doi.org/10.1016/j.bmc.2012.03.021] [PMID: 22475926]
[26]
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]
[27]
Abouzid, K.; Bekhit, S.A. Novel anti-inflammatory agents based on pyridazinone scaffold; design, synthesis and in vivo activity. Bioorg. Med. Chem., 2008, 16(10), 5547-5556.
[http://dx.doi.org/10.1016/j.bmc.2008.04.007] [PMID: 18430576]
[28]
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, 2077-2092.
[29]
Asif, M. Synthesis and analgesic activity of 6-(3--nitrophenyl)-4-substituted benzylidene-4,5 dihydropyridazin-3(2H)-one derivatives. Indones. J. Pharm., 2013, 23, 254-258.
[30]
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]
[31]
Tiryaki, D.; Sukuroglu, M.; Dogruer, D.S.; Akkol, E.; Ozgen, S.; Sahin, M.F. Synthesis of some new 2,6-disubstituted-3(2H)-pyridazinone derivatives and investigation of their analgesic, anti-inflammatory and antimicrobial activities. Med. Chem. Res., 2013, 22(6), 2553-2560.
[http://dx.doi.org/10.1007/s00044-012-0253-1]
[32]
Gokçe, M.; Dogruer, D.; Sahin, M.F. Synthesis and antinociceptive activity of 6-substituted-3-pyridazinone derivatives. Farmaco, 2001, 56(3), 233-237.
[http://dx.doi.org/10.1016/S0014-827X(01)01037-0] [PMID: 11409332]
[33]
Dogruer, D.S.; Fethi Sahin, M. ünlü, S.; Ito, S. Studies on some 3(2H)-pyridazinone derivatives with antinociceptive activity. Arch. Pharm., 2000, 333(4), 79-86.
[http://dx.doi.org/10.1002/(SICI)1521-4184(20004)333:4<79:AID-ARDP79>3.0.CO;2-S] [PMID: 10816899]
[34]
Banerjee, P.S.; Sharma, P.K.; Nema, R.K. Synthesis and anticonvulsant activity of pyridazinone derivatives. Int. J. Chemtech Res., 2009, 1, 522-525.
[35]
Siddiqui, A.A.; Dogra, A.A. Synthesis and anti-inflammatory activity of some 2,6-diphenyl 2,3,4,5-tetrahydro-3-pyridazinones. Indian J. Heterocycl. Chem., 2001, 10, 215.
[36]
Sircar, I.; Steffen, R.P.; Bobowski, G.; Burke, S.E.; Newton, R.S.; Weishaar, R.E.; Bristol, J.A.; Evans, D.B. Cardiotonic agents. 9. Synthesis and biological evaluation of a series of (E)-4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]ethenyl]-3(2H)-pyridazinones: A novel class of compounds with positive inotropic, antithrombotic, and vasodilatory activities for the treatment of congestive heart failure. J. Med. Chem., 1989, 32(2), 342-350.
[http://dx.doi.org/10.1021/jm00122a011] [PMID: 2536438]
[37]
Combs, D.W.; Rampulla, M.S.; Bell, S.C.; Klaubert, D.H.; Tobia, A.J.; Falotico, R.; Haertlein, B.; Lakas-Weiss, C.; Moore, J.B. 6-Benzoxazinylpyridazin-3-ones: Potent, long-acting positive inotrope and peripheral vasodilator agents. J. Med. Chem., 1990, 33(1), 380-386.
[http://dx.doi.org/10.1021/jm00163a061] [PMID: 2153210]
[38]
Nomoto, Y.; Takai, H.; Ohno, T.; Nagashima, K.; Yao, K.; Yamada, K.; Kubo, K.; Ichimura, M.; Mihara, A.; Kase, H. Studies of cardiotonic agents. 8. Synthesis and biological activities of optically active 6-(4-(benzylamino)-7-quinazolinyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone (KF15232). J. Med. Chem., 1996, 39(1), 297-303.
[http://dx.doi.org/10.1021/jm950197j] [PMID: 8568820]
[39]
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., 1996, 44(11), 2061-2069.
[http://dx.doi.org/10.1248/cpb.44.2061] [PMID: 8945771]
[40]
Laguna, R.; Rodriguez-Linared, B.; Cano, E.; Estevez, I.; Raviña, E.; Sotelo, E. Pyridazines. XIII. Synthesis of 6-aryl-5-oxygenated substituted-3(2H)-pyridazinones and evaluation as platelet aggregation inhibitors. Chem. Pharm. Bull., 1997, 45(7), 1151-1155.
[http://dx.doi.org/10.1248/cpb.45.1151] [PMID: 9246748]
[41]
Cinone, N.; Carrieri, A.; Strappaghetti, G.; Corsano, S.; Barbaro, R.; Carotti, A. Comparative molecular field analysis of some pyridazinone-containing α1-Antagonists. Bioorg. Med. Chem., 1999, 7(11), 2615-2620.
[http://dx.doi.org/10.1016/S0968-0896(99)00211-4] [PMID: 10632072]
[42]
Bristol, J.A.; Sircar, I.; Moos, W.H.; Evans, D.B.; Weishaar, R.E. Cardiotonic agents. 1. 4,5-Dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3 (2H)-pyridazinones:Novel positive inotropic agents for the treatment ofcongestive heart failure. J. Med. Chem., 1984, 27(9), 1099-101.
[http://dx.doi.org/10.1021/jm00375a001]
[43]
Toller, W.G.; Pagel, P.S.; Kersten, J.R.; Warltier, D.C. Levosimendan. Drugs Future, 2000, 25(6), 0563.
[http://dx.doi.org/10.1358/dof.2000.025.06.580665]
[44]
Siddiqui, A.A.; Wani, S.M. Synthesis and hypotensive activity of some 6-(substituted aryl)-4-methyl-2,3- dihydropyridazin-3-ones. Indian J. Chem., 2004, 43B, 1574-1579.
[45]
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]
[46]
Siddiqui, A.A.; Mishra, R.; Shaharyar, M.; Husain, A.; Rashid, M.; Pal, P. Triazole incorporated pyridazinones as a new class of antihypertensive agents: Design, synthesis and in vivo screening. Bioorg. Med. Chem. Lett., 2011, 21(3), 1023-1026.
[http://dx.doi.org/10.1016/j.bmcl.2010.12.028] [PMID: 21211966]
[47]
Ibrahim, H.M.; Behbehani, H.; Elnagdi, M.H. Approaches towards the synthesis of a novel class of 2-amino-5-arylazonicotinate, pyridazinone and pyrido[2,3-d]pyrimidine derivatives as potent antimicrobial agents. Chem. Cent. J., 2013, 7(1), 123.
[http://dx.doi.org/10.1186/1752-153X-7-123] [PMID: 23867062]
[48]
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]
[49]
Peesapati, V.; Venkata, S.C. Synthesis and antimicrobial activity of new triazolo/tetrazolo-pyridazine [6,7] benzocycloheptenes. Indian J. Chem., 2002, 41B, 839-844.
[50]
Mogilaiah, K.; Kankaiah, G. Synthesis of 6-aryl-2-(2-phenyl-1,8-naphthyridine-3-carbonyl)-4,5-dihydropyridazin- 3(2H)-ones. Indian J. Chem., 2003, 42B, 658-660.
[51]
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]
[52]
AbdEl-Ghani E.; Assy, M.G.; Moustafa, H.Y. Synthesis and biological activity of some new pyridazine derivatives. Monatsh. Chem., 1995, 126(11), 1265-1270.
[http://dx.doi.org/10.1007/BF00824306]
[53]
Cao, S.; Lu, D-L.; Zhao, C.M.; Li, L-N.; Huang, Q.C.; Qian, X.H. An efficient and practical method for the synthesis of 1-(2,6-difluorobenzoyl)-3-(2-alkyl-3-oxopyridazin-4-yl)ureas as potential chitin synthesis inhibitors. Monatsh. Chem., 2006, 137(6), 779-784.
[http://dx.doi.org/10.1007/s00706-005-0476-7]
[54]
Coudert, P.; Rubat, C.; Couquelet, J.; Fialip, J.; Bastide, P.; Privat, A.P. Synthe’se et recherche d’une activite’anti-convulsivante dans une nouvelle se’rie de diaryl-4,6 pyridazinones-3N-substitue’es. Eur. J. Med. Chem., 1989, 24(5), 551-555.
[http://dx.doi.org/10.1016/0223-5234(89)90062-7]
[55]
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-pyridaziny-lacetylhydrazides. Chem. Pharm. Bull., 1990, 38(11), 3009-3013.
[http://dx.doi.org/10.1248/cpb.38.3009] [PMID: 2128224]
[56]
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]
[57]
Prous, J.; Mealy, N.; Castañer, J. Zopolrestat < Rec INN; BAN; USAN >. Drugs Future, 1995, 20(1), 33.
[http://dx.doi.org/10.1358/dof.1995.020.01.279128]
[58]
Costantino, L.; Rastelli, G.; Vescovini, K.; Cignarella, G.; Vianello, P.; Del Corso, A.; Cappiello, M.; Mura, U.; Barlocco, D. Synthesis, activity, and molecular modeling of a new series of tricyclic pyridazinones as selective aldose reductase inhibitors. J. Med. Chem., 1996, 39(22), 4396-4405.
[http://dx.doi.org/10.1021/jm960124f] [PMID: 8893834]
[59]
Rubat, C.; Coudert, P.; Bastide, P.; Tronche, P. Antidepressant activity of new 3-amino-5-disubstituted benzylidene-6-methyl-(4H)-pyridazine derivatives. Chem. Pharm. Bull., 1988, 36(12), 5000-5003.
[http://dx.doi.org/10.1248/cpb.36.5000] [PMID: 3246058]
[60]
Livermore, D.G.H.; Bethell, R.C.; Cammack, N.; Hancock, A.P.; Hann, M.M.; Green, D.V.S.; Lamont, R.B.; Noble, S.A.; Orr, D.C.; Payne, J.J.; Ramsey, M.V.J.; Shingler, A.H.; Smith, C.; Storer, R.; Williamson, C.; Willson, T. Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines. J. Med. Chem., 1993, 36(24), 3784-3794.
[http://dx.doi.org/10.1021/jm00076a005] [PMID: 7504733]
[61]
Ellis, D.A.; Blazel, J.K.; Webber, S.E.; Tran, C.V.; Dragovich, P.S.; Sun, Z.; Ruebsam, F.; McGuire, H.M.; Xiang, A.X.; Zhao, J.; Li, L.S.; Zhou, Y.; Han, Q.; Kissinger, C.R.; Showalter, R.E.; Lardy, M.; Shah, A.M.; Tsan, M.; Patel, R.; LeBrun, L.A.; Kamran, R.; Bartkowski, D.M.; Nolan, T.G.; Norris, D.A.; Sergeeva, M.V.; Kirkovsky, L. 4-(1,1-Dioxo-1,4-dihydro-1λ6-benzo[1,4]thiazin-3-yl)-5-hydroxy-2H-pyridazin-3-ones as potent inhibitors of HCV NS5B polymerase. Bioorg. Med. Chem. Lett., 2008, 18(16), 4628-4632.
[http://dx.doi.org/10.1016/j.bmcl.2008.07.014] [PMID: 18662878]
[62]
Çalişkan-Ergün, B.; şüküroğlu, M.; Coban, T.; Banoğlu, E.; Suzen, S. Screening and evaluation of antioxidant activity of some pyridazine derivatives. J. Enzyme Inhib. Med. Chem., 2008, 23(2), 225-229.
[http://dx.doi.org/10.1080/14756360701475167] [PMID: 18343908]
[63]
Yamalı C.; Ozan Gülcan, H.; Kahya, B.; Çobanoğlu, S.; Kadir Şüküroğlu, M.; Doğruer, D.S. Synthesis of some 3(2H)-pyridazinone and 1(2H)-phthalazinone derivatives incorporating aminothiazole moiety and investigation of their antioxidant, acetylcholinesterase, and butyrylcholinesterase inhibitory activities. Med. Chem. Res., 2015, 24(3), 1210-1217.
[http://dx.doi.org/10.1007/s00044-014-1205-8]
[64]
Hirata, K.; Kudo, M.; Miyake, T.; Kawamura, Y.; Ogura, T. NC-129-A new acaricide. Proceedings of the Brighton Crop Prot Conf-Pests Dis, Hilton Brighton Metropole, Brighton, UK21–24 November 1988, pp. 21-241.
[65]
Miyake, T.; Haruyama, H.; Mitsui, T.; Sakurai, A. Effects of a new juvenile hormone mimic, NC-170, on metamorphosis and diapause of the small brown planthopper, Laodelphax striatellus. J. Pestic. Sci., 1992, 17(1), 75-82.
[http://dx.doi.org/10.1584/jpestics.17.75]
[66]
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]
[67]
Smith, D.T.; Meggitt, W.F. Persistence and degradation of pyrazon in soil. Weed Sci., 1970, 18(2), 260-264.
[http://dx.doi.org/10.1017/S0043174500079704]
[68]
Smith, D.T.; Meggitt, W.F. Movement and distribution of pyrazon in soil. Weed Sci., 1970, 18(2), 255-259.
[http://dx.doi.org/10.1017/S0043174500079698]
[69]
Jamet, P.; Piedallu, M.A. Study of the adsorption and desorption of pyrazone (5-amino-4-chloro-2-phenyl-2H-3-pyridazinone) by different types of soils. Weed Res., 1975, 15(2), 113-121.
[http://dx.doi.org/10.1111/j.1365-3180.1975.tb01108.x]
[70]
Jamet, P. Comparative Studies of Food and Environmental Contamination; International Atomic Energy Agency, 1974.
[71]
Csókás, D.; Zupkó, I.; Károlyi, B.I.; Drahos, L.; Holczbauer, T.; Palló, A.; Czugler, M.; Csámpai, A. Synthesis, spectroscopy, X-ray analysis and in vitro antiproliferative effect of ferrocenylmethylene-hydrazinylpyridazin-3(2H)-ones and related ferroceno[d]pyridazin-1(2H)-ones. J. Organomet. Chem., 2013, 743, 130-138.
[http://dx.doi.org/10.1016/j.jorganchem.2013.06.040]
[72]
Banerjee, P.S. Various biological activities of pyridazinone ring derivatives. Asian J. Chem., 2011, 23(5), 1905-1910.
[73]
Baytaş S.; İnceler, N.; Mavaneh, K.F.; Uludağ M.O.; Abacioğlu, N.; Gökçe, M. Synthesis of antipyrine/pyridazinone hybrids and investigation of their in vivo analgesic and anti-inflammatory activities. Turk. J. Chem., 2012, 36, 734-748.
[http://dx.doi.org/10.3906/kim-1111-29]
[74]
Sharma, B.; Verma, A.; Sharma, U.K.; Prajapati, S. Efficient synthesis, anticonvulsant and muscle relaxant activities of new 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives. Med. Chem. Res., 2014, 23(1), 146-157.
[http://dx.doi.org/10.1007/s00044-013-0618-0]
[75]
Boukharsa, Y.; Zaoui, Y.; Taoufik, J.; Ansar, M. Pyridazin-3(2H)-ones: Synthesis, reactivity, applications in pharmacology and agriculture. J. Chem. Pharm. Res., 2014, 6(12), 297-310.
[76]
Alghamdi, S.; Imran, M.; Kamal, M.; Asif, M. Synthesis, characterization and antimycobacterial activity of some substituted phenylpyridazinone derivatives. Pharm. Chem. J., 2022, 55(12), 1367-1371.
[http://dx.doi.org/10.1007/s11094-022-02583-5]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy