Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Mini-Review Article

Diverse Pharmacological Potential of different Substituted Pyrazole Derivatives

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

Volume 21, Issue 7, 2024

Published on: 12 October, 2023

Page: [858 - 888] Pages: 31

DOI: 10.2174/0115701794260444230925095804

Price: $65

Abstract

The chemistry of heterocyclic compounds has been a topic of research interest. Some five-membered heterocyclic compounds have been the subject of extensive research due to their different types of pharmacological effects. The five-membered nitrogen-containing heterocyclic compounds pyrazole, pyrazoline, and pyrazolone derivatives have a lot of interest in the fields of medical and agricultural chemistry due to their diverse spectrum of therapeutic activities. Various substituted pyrazole, pyrazoline, and pyrazolone compounds exhibited diverse pharmacological effects like Anti-microbial, anti-inflammatory, anti-tubercular, anti-fungal, anti-malarial, anti-diabetic, diuretic, anti-depressant, anticonvulsant, antioxidant, anti-leishmanial, antidiabetic, and antiviral, etc. In recent decades, the synthesis of numerous pyrazole, pyrazoline, and pyrazolone derivatives by different synthetic methods as well as research into their chemical and biological behavior have become more important. This review focuses on synthetic methods of the pyrazole, pyrazoline, and pyrazolone derivatives, which have significant biological properties and a variety of applications.

Keywords: Pyrazole, pyrazoline, pyrazolone, antimicrobial, antitubercular, antifungal, anti-inflammatory, anticancer, heterocyclic compounds.

Graphical Abstract
[1]
Vincent, C.; Krishnakumar, K.; Elias, G. Pharmacological Potential of A Resourceful Heterocycle: Pyrazoline-A Review. Am J PharmTech Res., 2020, 10(3), 111-124.
[2]
Yusuf, M.; Jain, P. Synthetic and biological studies of pyrazolines and related heterocyclic compounds. Arab. J. Chem., 2014, 7(5), 553-596.
[http://dx.doi.org/10.1016/j.arabjc.2011.09.013]
[3]
Marella, A.; Rahmat Ali, M.; Tauquir Alam, M.; Saha, R.; Tanwar, O.; Akhter, M.; Shaquiquzzaman, M.; Mumtaz Alam, M. Pyrazolines: a biological review. Mini Rev. Med. Chem., 2013, 13(6), 921-931.
[http://dx.doi.org/10.2174/1389557511313060012] [PMID: 23544604]
[4]
Zhu, S.L.; Wu, Y.; Liu, C.J.; Wei, C.Y.; Tao, J.C.; Liu, H.M. Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents. Eur. J. Med. Chem., 2013, 65, 70-82.
[http://dx.doi.org/10.1016/j.ejmech.2013.04.044] [PMID: 23693151]
[5]
Kumar, A.; Varadaraj, B.G.; Singla, R.K. Synthesis and evaluation of antioxidant activity of novel 3,5-disubstituted-2-pyrazolines. Bull. Fac. Pharm. Cairo Univ., 2013, 51(2), 167-173.
[http://dx.doi.org/10.1016/j.bfopcu.2013.04.002]
[6]
Surendra Kumar, R.; Arif, I.A.; Ahamed, A.; Idhayadhulla, A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J. Biol. Sci., 2016, 23(5), 614-620.
[http://dx.doi.org/10.1016/j.sjbs.2015.07.005] [PMID: 27579011]
[7]
Aggarwal, S.; Paliwal, D.; Kaushik, D.; Gupta, G.K.; Kumar, A. Synthesis, Antimalarial evaluation and sar study of some 1,3,5-trisubstituted pyrazoline derivatives. Lett. Org. Chem., 2019, 16(10), 807-817.
[http://dx.doi.org/10.2174/1570178616666190212145754]
[8]
Harathi, P.; Prasad, R.; Satyavati, D.; Subramanian, S. Synthesis, characterization and anti-inflammatory activity of novel pyrazole derivatives. Asian J. Pharm. Clin. Res., 2015, 8(5), 82-86.
[9]
Ahsan, M.J. Anticonvulsant activity and neuroprotection assay of 3-substituted-N-aryl-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide analogues. Arab. J. Chem., 2017, 10, S2762-S2766.
[http://dx.doi.org/10.1016/j.arabjc.2013.10.023]
[10]
Elderfield, R.C. Heterocyclic Compounds;; John Wiley & Sons Inc., 1957, 5, pp. 45-161.
[11]
Avupati, V.R.; Yejella, R.P. Bioactive pyrazolines: An update. World J. Pharm. Res., 2014, 3, 1181-1215.
[12]
Wang, Q.; Hong, G.; Tang, Z.; Yang, P.; Zhong, Y.; Gong, Y.; Wang, L. Divergent Synthesis of 3,5‐disubstituted pyrazoles and α, β ‐alkynic hydrazone from diarylpropynones and carbazates. Asian J. Org. Chem., 2022, 11(2), e202100794.
[http://dx.doi.org/10.1002/ajoc.202100794]
[13]
Overberger, C.G.; Weinshenker, N.; Anselme, J-P. The synthesis and the decomposition of cis- and trans-3,5-Bis(p-anisyl)-1-pyrazolines. J. Am. Chem. Soc., 1965, 87(18), 4119-4124.
[http://dx.doi.org/10.1021/ja01096a021]
[14]
Pugh, W.; Stephen, A.M. The chlorostannates of hydrazine and 3: 5: 5-trimethyl-pyrazoline. J. Chem. Soc., 1952, 10, 4138-4141.
[http://dx.doi.org/10.1039/jr9520004138]
[15]
Raiford, L.C.; Entrikin, J.B. Rearrangement of the phenylhydrazones of some unsymmetrically substituted dibenzalacetones. J. Am. Chem. Soc., 1933, 55(3), 1125-1128.
[http://dx.doi.org/10.1021/ja01330a043]
[16]
Anjaneyulu, S.R.; Murthy, Y.L.N. Synthesis of fused pyrimidine derivatives from chalcones. Indian. J. Chem., 1995, 34(B), 933.
[17]
Jadhav, S.Y.; Shirame, S.P.; Kulkarni, S.D.; Patil, S.B.; Pasale, S.K.; Bhosale, R.B. PEG mediated synthesis and pharmacological evaluation of some fluoro substituted pyrazoline derivatives as antiinflammatory and analgesic agents. Bioorg. Med. Chem. Lett., 2013, 23(9), 2575-2578.
[http://dx.doi.org/10.1016/j.bmcl.2013.02.105] [PMID: 23541672]
[18]
Amin, K.M.; Eissa, A.A.M.; Abou-Seri, S.M.; Awadallah, F.M.; Hassan, G.S. Synthesis and biological evaluation of novel coumarin–pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents. Eur. J. Med. Chem., 2013, 60, 187-198.
[http://dx.doi.org/10.1016/j.ejmech.2012.12.004] [PMID: 23291120]
[19]
Wang, H.H.; Qiu, K.M.; Cui, H.E.; Yang, Y.S. Yin-Luo; Xing, M.; Qiu, X.Y.; Bai, L.F.; Zhu, H.L. Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents. Bioorg. Med. Chem., 2013, 21(2), 448-455.
[http://dx.doi.org/10.1016/j.bmc.2012.11.020] [PMID: 23245802]
[20]
Yang, W.; Hu, Y.; Yang, Y.S.; Zhang, F.; Zhang, Y.B.; Wang, X.L.; Tang, J.F.; Zhong, W.Q.; Zhu, H.L. Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazoline derivatives with/without thiourea skeleton as anticancer agents. Bioorg. Med. Chem., 2013, 21(5), 1050-1063.
[http://dx.doi.org/10.1016/j.bmc.2013.01.013] [PMID: 23391364]
[21]
Bhandari, S.; Tripathi, A.C.; Saraf, S.K. Novel 2-pyrazoline derivatives as potential anticonvulsant agents. Med. Chem. Res., 2013, 22(11), 5290-5296.
[http://dx.doi.org/10.1007/s00044-013-0530-7]
[22]
Desai, N.C.; Joshi, V.V.; Rajpara, K.M.; Vaghani, H.V.; Satodiya, H.M. Synthesis of quinoline-pyrazoline based thiazole derivatives endowed with antimicrobial activity. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem., 2013, 52, 1191-1201.
[23]
Mandawad, G.G.; Dawane, B.S.; Beedkar, S.D.; Khobragade, C.N.; Yemul, O.S. Trisubstituted thiophene analogues of 1-thiazolyl-2-pyrazoline, super oxidase inhibitors and free radical scavengers. Bioorg. Med. Chem., 2013, 21(1), 365-372.
[http://dx.doi.org/10.1016/j.bmc.2012.09.060] [PMID: 23177727]
[24]
Patel, P.A.; Bhadani, V.N.; Bhatt, P.V.; Purohita, D.M. Synthesis and biological evaluation of novel chalcone and pyrazoline derivatives bearing substituted vanillin nucleus. J. Heterocycl. Chem., 2014, 52(4), 1119-1125.
[http://dx.doi.org/10.1002/jhet.2215]
[25]
El-Behairy, M.F.; Mazeed, T.E.; El-Azzouny, A.A.; Aboul-Enein, M.N. Design, synthesis and antibacterial potential of 5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-1-substituted-4,5-dihydropyrazoles. Saudi Pharm. J., 2015, 23(2), 202-209.
[http://dx.doi.org/10.1016/j.jsps.2014.07.009] [PMID: 25972742]
[26]
Ovais, S.; Pushpalatha, H.; Reddy, G.B.; Rathore, P.; Bashir, R.; Yaseen, S.; Dheyaa, A.; Yaseen, R.; Tanwar, O.; Akthar, M.; Samim, M.; Javed, K. Synthesis and biological evaluation of some new pyrazoline substituted benzenesulfonylurea/thiourea derivatives as anti-hyperglycaemic agents and aldose reductase inhibitors. Eur. J. Med. Chem., 2014, 80, 209-217.
[http://dx.doi.org/10.1016/j.ejmech.2014.04.046] [PMID: 24780598]
[27]
Kharbanda, C.; Alam, M.S.; Hamid, H.; Javed, K.; Shafi, S.; Ali, Y.; Alam, P.; Pasha, M.A.Q.; Dhulap, A.; Bano, S.; Nazreen, S.; Haider, S. Novel benzenesulfonylureas containing thiophenylpyrazoline moiety as potential antidiabetic and anticancer agents. Bioorg. Med. Chem. Lett., 2014, 24(22), 5298-5303.
[http://dx.doi.org/10.1016/j.bmcl.2014.09.044] [PMID: 25442322]
[28]
Kankanala, K.; Reddy, V.R.; Devi, Y.P.; Mangamoori, L.N.; Rambabu, D.; Mukkanti, K.; Pal, S. Nonsteroidal anti-inflammatory drug-based N-allylidene benzohydrides and 1-acyl-2-pyrazolines: Their synthesis as potential cytotoxic agents in vitro. J. Heterocycl. Chem., 2014, 52(1)
[http://dx.doi.org/10.1002/jhet]
[29]
Evranos-Aksöz, B.; Yabanoğlu-Çiftçi, S.; Uçar, G.; Yelekçi, K.; Ertan, R. Synthesis of some novel hydrazone and 2-pyrazoline derivatives: Monoamine oxidase inhibitory activities and docking studies. Bioorg. Med. Chem. Lett., 2014, 24(15), 3278-3284.
[http://dx.doi.org/10.1016/j.bmcl.2014.06.015] [PMID: 24986657]
[30]
Neudorfer, C.; Shanab, K.; Jurik, A.; Schreiber, V.; Neudorfer, C.; Vraka, C.; Schirmer, E.; Holzer, W.; Ecker, G.; Mitterhauser, M.; Wadsak, W.; Spreitzer, H. Development of potential selective and reversible pyrazoline based MAO-B inhibitors as MAO-B PET tracer precursors and reference substances for the early detection of Alzheimer’s disease. Bioorg. Med. Chem. Lett., 2014, 24(18), 4490-4495.
[http://dx.doi.org/10.1016/j.bmcl.2014.07.085] [PMID: 25127869]
[31]
Shaikh, M.U.; Jadhav, G.R.; Kale, R.P.; Chate, A.V.; Nagargoje, D.R.; Gill, C.H. Synthesis and antimicrobial screening of some novel 2-(5-(4-(1 H -Benzo[ d][1,2,3]triazol-1-yl)phenyl)-4,5-dihydro-1 H -pyrazol-3-yl)phenols incorporated by triazole moiety. J. Heterocycl. Chem., 2014, 51(2), 513-517.
[http://dx.doi.org/10.1002/jhet.1646]
[32]
Desai, K.G.; Naik, J.I.; Raval, J.P.; Desai, K.R. Microwave-induced and conventional heterocyclic synthesis: An antimicrobial entites of newer quinazolinyl-Δ2-pyrazolines. Arab. J. Chem., 2014, 7(5), 597-603.
[http://dx.doi.org/10.1016/j.arabjc.2011.06.015]
[33]
Kumar, J.; Chawla, G.; Kumar, U.; Sahu, K. Design and syntheses of some new quinoxaline derivatives containing pyrazoline residue as potential antimicrobial agents. Med. Chem. Res., 2014, 23(9), 3929-3940.
[http://dx.doi.org/10.1007/s00044-014-0976-2]
[34]
Abdel-Halim, M.; Diesel, B.; Kiemer, A.K.; Abadi, A.H.; Hartmann, R.W.; Engel, M. Discovery and optimization of 1,3,5-trisubstituted pyrazolines as potent and highly selective allosteric inhibitors of protein kinase C-ζ. J. Med. Chem., 2014, 57(15), 6513-6530.
[http://dx.doi.org/10.1021/jm500521n] [PMID: 25058929]
[35]
Zhang, F.G.; Wei, Y.; Yi, Y.P.; Nie, J.; Ma, J.A. Regioselective cycloaddition of trifluorodiazoethane with electron-deficient allenic esters and ketones: access to CF3-substituted pyrazolines and pyrazoles. Org. Lett., 2014, 16(11), 3122-3125.
[http://dx.doi.org/10.1021/ol501249h] [PMID: 24850209]
[36]
Mahmoodi, N.O.; Sharifzadeh, B.; Mamaghani, M.; Tabatabaeian, K. Evaluating the synthesis of bis-pyrazolines. J. Heterocycl. Chem., 2014, 51(2), 336-342.
[http://dx.doi.org/10.1002/jhet.1683]
[37]
Barsoum, F.F.; Hosni, H.M.; Girgis, A.S. Novel bis(1-acyl-2-pyrazolines) of potential anti-inflammatory and molluscicidal properties. Bioorg. Med. Chem., 2006, 14(11), 3929-3937.
[http://dx.doi.org/10.1016/j.bmc.2006.01.042] [PMID: 16460945]
[38]
Kaplancikli, Z.A.; Turan-Zitouni, G.; Özdemir, A.; Devrim Can, Ö.; Chevallet, P. Synthesis and antinociceptive activities of some pyrazoline derivatives. Eur. J. Med. Chem., 2009, 44(6), 2606-2610.
[http://dx.doi.org/10.1016/j.ejmech.2008.09.002] [PMID: 18922604]
[39]
Reddy, M.V.R.; Billa, V.K.; Pallela, V.R.; Mallireddigari, M.R.; Boominathan, R.; Gabriel, J.L.; Reddy, E.P. Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors. Bioorg. Med. Chem., 2008, 16(7), 3907-3916.
[http://dx.doi.org/10.1016/j.bmc.2008.01.047] [PMID: 18272371]
[40]
Sahu, S.K.; Banerjee, M.; Samantray, A.; Behera, C.; Azam, M.A. Synthesis, analgesic, anti-inflammatory and antimicrobial activities of some novel pyrazoline derivatives. Trop. J. Pharm. Res., 2008, 7(2), 961-968.
[http://dx.doi.org/10.4314/tjpr.v7i2.14664]
[41]
Amir, M.; Kumar, H.; Khan, S.A. Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg. Med. Chem. Lett., 2008, 18(3), 918-922.
[http://dx.doi.org/10.1016/j.bmcl.2007.12.043] [PMID: 18182288]
[42]
Rathish, I.G.; Javed, K.; Ahmad, S.; Bano, S.; Alam, M.S.; Pillai, K.K.; Singh, S.; Bagchi, V. Synthesis and antiinflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide. Bioorg. Med. Chem. Lett., 2009, 19(1), 255-258.
[http://dx.doi.org/10.1016/j.bmcl.2008.10.105] [PMID: 19010670]
[43]
Khode, S.; Maddi, V.; Aragade, P.; Palkar, M.; Ronad, P.K.; Mamledesai, S.; Thippeswamy, A.H.M.; Satyanarayana, D. Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 2009, 44(4), 1682-1688.
[http://dx.doi.org/10.1016/j.ejmech.2008.09.020] [PMID: 18986738]
[44]
Sharma, P.K.; Kumar, S.; Kumar, P.; Kaushik, P.; Kaushik, D.; Dhingra, Y.; Aneja, K.R. Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory–antimicrobial agents. Eur. J. Med. Chem., 2010, 45(6), 2650-2655.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.059] [PMID: 20171763]
[45]
Chandra, T.; Garg, N.; Lata, S.; Saxena, K.K.; Kumar, A. Synthesis of substituted acridinyl pyrazoline derivatives and their evaluation for anti-inflammatory activity. Eur. J. Med. Chem., 2010, 45(5), 1772-1776.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.009] [PMID: 20149499]
[46]
Fioravanti, R.; Bolasco, A.; Manna, F.; Rossi, F.; Orallo, F.; Ortuso, F.; Alcaro, S.; Cirilli, R. Synthesis and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors. Eur. J. Med. Chem., 2010, 45(12), 6135-6138.
[http://dx.doi.org/10.1016/j.ejmech.2010.10.005] [PMID: 20974503]
[47]
Joshi, R.S.; Mandhane, P.G.; Diwakar, S.D.; Dabhade, S.K.; Gill, C.H. Synthesis, analgesic and anti-inflammatory activities of some novel pyrazolines derivatives. Bioorg. Med. Chem. Lett., 2010, 20(12), 3721-3725.
[http://dx.doi.org/10.1016/j.bmcl.2010.04.082] [PMID: 20529688]
[48]
Girisha, K.S.; Kalluraya, B.; Narayana, V. Padmashree, Synthesis and pharmacological study of 1-acetyl/propyl-3-aryl-5-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-pyrazoline. Eur. J. Med. Chem., 2010, 45(10), 4640-4644.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.032] [PMID: 20702008]
[49]
Bano, S.; Javed, K.; Ahmad, S.; Rathish, I.G.; Singh, S.; Alam, M.S. Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents. Eur. J. Med. Chem., 2011, 46(12), 5763-5768.
[http://dx.doi.org/10.1016/j.ejmech.2011.08.015] [PMID: 22019186]
[50]
Bashir, R.; Ovais, S.; Yaseen, S.; Hamid, H.; Alam, M.S.; Samim, M.; Singh, S.; Javed, K. Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents. Bioorg. Med. Chem. Lett., 2011, 21(14), 4301-4305.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.061] [PMID: 21664130]
[51]
Burguete, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Ancizu, S.; Villar, R.; Solano, B.; Moreno, E.; Torres, E.; Pérez, S.; Aldana, I.; Monge, A. Synthesis and biological evaluation of new quinoxaline derivatives as antioxidant and anti-inflammatory agents. Chem. Biol. Drug Des., 2011, 77(4), 255-267.
[http://dx.doi.org/10.1111/j.1747-0285.2011.01076.x] [PMID: 21244639]
[52]
Özkay, Ü.D.; Can, Ö.D.; Kaplancıklı, Z.A. Antinociceptive activities of some triazole and pyrazoline moieties-bearing compounds. Med. Chem. Res., 2012, 21(7), 1056-1061.
[http://dx.doi.org/10.1007/s00044-011-9619-z]
[53]
Samshuddin, S.; Narayana, B.; Sarojini, B.K.; Khan, M.T.H.; Yathirajan, H.S.; Raj, C.G.D.; Raghavendra, R. Antimicrobial, analgesic, DPPH scavenging activities and molecular docking study of some 1,3,5-triaryl-2-pyrazolines. Med. Chem. Res., 2012, 21(8), 2012-2022.
[http://dx.doi.org/10.1007/s00044-011-9735-9]
[54]
Ovais, S.; Bashir, R.; Yaseen, S.; Rathore, P.; Samim, M.; Javed, K. Synthesis and pharmacological evaluation of some novel 2-pyrazolines bearing benzenesulfonamide as anti-inflammatory and blood glucose lowering agents. Med. Chem. Res., 2013, 22(3), 1378-1385.
[http://dx.doi.org/10.1007/s00044-012-0130-y]
[55]
Carradori, S.; Secci, D.; Bolasco, A.; De Monte, C.; Yáñez, M. Synthesis and selective inhibitory activity against human COX-1 of novel 1-(4-substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline derivatives. Arch. Pharm. (Weinheim), 2012, 345(12), 973-979.
[http://dx.doi.org/10.1002/ardp.201200249] [PMID: 22961586]
[56]
Ningaiah, S.; Bhadraiah, U.K.; Keshavamurthy, S.; Javarasetty, C. Novel pyrazoline amidoxime and their 1,2,4-oxadiazole analogues: Synthesis and pharmacological screening. Bioorg. Med. Chem. Lett., 2013, 23(16), 4532-4539.
[http://dx.doi.org/10.1016/j.bmcl.2013.06.042] [PMID: 23850201]
[57]
Jadhav, S.B.; Shastri, R.A.; Gaikwad, K.V.; Gaikwad, S.V. Synthesis and antimicrobial studies of some novel pyrazoline and isoxazoline derivatives. E-J. Chem., 2009, 6(S1), S183-S188.
[http://dx.doi.org/10.1155/2009/361564]
[58]
Yu, M.; Yang, H.; Wu, K.; Ji, Y.; Ju, L.; Lu, X. Novel pyrazoline derivatives as bi-inhibitor of COX-2 and B-Raf in treating cervical carcinoma. Bioorg. Med. Chem., 2014, 22(15), 4109-4118.
[http://dx.doi.org/10.1016/j.bmc.2014.05.059] [PMID: 24934992]
[59]
Munawar, M.; Azad, M.; Athar, M.; Groundwater, P. Synthesis and antimicrobial activity of quinoline-based 2-pyrazolines. Chem. Pap., 2008, 62(3), 288-293.
[http://dx.doi.org/10.2478/s11696-008-0025-z]
[60]
Zhao, P.L.; Wang, F.; Zhang, M.Z.; Liu, Z.M.; Huang, W.; Yang, G.F. Synthesis, fungicidal, and insecticidal activities of β-Methoxyacrylate-containing N-acetyl pyrazoline derivatives. J. Agric. Food Chem., 2008, 56(22), 10767-10773.
[http://dx.doi.org/10.1021/jf802343p] [PMID: 18973342]
[61]
Solankee, A.; Prajapati, Y. An efficient synthesis of some new fluorine containing acetyl pyrazoline and isoxazole derivatives and their antibacterial activity. Rasayan J. Chem., 2009, 2, 23-27.
[62]
Chaitanya, S.K.; Ishwar, B.K.; Revanna, S.B.C.; Satyanarayana, D.; Kalluraya, B. Synthesis and biological activity studies of some pyrazoline derivatives containing quinoline moiety. J. Ind. Counc. Chem., 2009, 26, 37-40.
[63]
Hu, L.; Lan, P.; Song, Q.L.; Huang, Z.J.; Sun, P.H.; Zhuo, C.; Wang, Y.; Xiao, S.; Chen, W.M. Synthesis and antibacterial activity of C-12 pyrazolinyl spiro ketolides. Eur. J. Med. Chem., 2010, 45(12), 5943-5949.
[http://dx.doi.org/10.1016/j.ejmech.2010.09.060] [PMID: 20970894]
[64]
Konda, S.G.; Valekar, A.H.; Lomate, S.T.; Lokhande, P.D.; Dawane, B.S. Synthesis and antibacterial studies of some new pyrazoline and isoxazoline derivatives. J. Chem. Pharm. Res., 2010, 2, 1-6.
[65]
Dawane, B.S.; Konda, S.G.; Mandawad, G.G.; Shaikh, B.M. Poly(ethylene glycol) (PEG-400) as an alternative reaction solvent for the synthesis of some new 1-(4-(4′-chlorophenyl)-2-thiazolyl)-3-aryl-5-(2-butyl-4-chloro-1H-imidazol-5yl)-2-pyrazolines and their in vitro antimicrobial evaluation. Eur. J. Med. Chem., 2010, 45(1), 387-392.
[http://dx.doi.org/10.1016/j.ejmech.2009.10.015] [PMID: 19896247]
[66]
Rani, M.; Yusuf, M.; Khan, S.A. Synthesis and in-vitro-antibacterial activity of [5-(furan-2-yl)-phenyl]-4,5-carbothioamide-pyrazolines. J. Saudi Chem. Soc., 2012, 16(4), 431-436.
[http://dx.doi.org/10.1016/j.jscs.2011.02.012]
[67]
Rani, M.; Yusuf, M.; Khan, S.A.; Sahota, P.P.; Pandove, G. Synthesis, studies and in-vitro antibacterial activity of N-substituted 5-(furan-2-yl)-phenyl pyrazolines. Arab. J. Chem., 2015, 8(2), 174-180.
[http://dx.doi.org/10.1016/j.arabjc.2010.10.036]
[68]
Rani, M.; Mohamad, Y. Synthesis, studies and in vitro antibacterial activity of some 5-(thiophene-2-yl)-phenyl pyrazoline derivatives. J. Saudi Chem. Soc., 2014, 18(5), 411-417.
[http://dx.doi.org/10.1016/j.jscs.2011.09.002]
[69]
Rostom, S.A.F.; Badr, M.H.; Abd El Razik, H.A.; Ashour, H.M.A.; Abdel Wahab, A.E. Synthesis of some pyrazolines and pyrimidines derived from polymethoxy chalcones as anticancer and antimicrobial agents. Arch. Pharm. (Weinheim), 2011, 344(9), 572-587.
[http://dx.doi.org/10.1002/ardp.201100077] [PMID: 21755528]
[70]
Siddiqui, Z.N.; Mohammed Musthafa, T.N.; Ahmad, A.; Khan, A.U. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg. Med. Chem. Lett., 2011, 21(10), 2860-2865.
[http://dx.doi.org/10.1016/j.bmcl.2011.03.080] [PMID: 21507638]
[71]
Desai, N.C.; Joshi, V.V.; Rajpara, K.M. Synthesis of new quinoline-2-pyrazoline-based thiazolinone derivatives as potential antimicrobial agents. Med. Chem. Res., 2013, 22(8), 3663-3674.
[http://dx.doi.org/10.1007/s00044-012-0377-3]
[72]
Agrawal, M.; Sonar, P.K.; Saraf, S.K. Synthesis of 1,3,5-trisubstituted pyrazoline nucleus containing compounds and screening for antimicrobial activity. Med. Chem. Res., 2012, 21(11), 3376-3381.
[http://dx.doi.org/10.1007/s00044-011-9871-2]
[73]
Deng, H.; Yu, Z.Y.; Shi, G.Y.; Chen, M.J.; Tao, K.; Hou, T.P. Synthesis and in vitro antifungal evaluation of 1,3,5-trisubstituted-2-pyrazoline derivatives. Chem. Biol. Drug Des., 2012, 79(3), 279-289.
[http://dx.doi.org/10.1111/j.1747-0285.2011.01308.x] [PMID: 22181692]
[74]
Abdel-Wahab, B.F.; Abdel-Latif, E.; Mohamed, H.A.; Awad, G.E.A. Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents. Eur. J. Med. Chem., 2012, 52, 263-268.
[http://dx.doi.org/10.1016/j.ejmech.2012.03.023] [PMID: 22480494]
[75]
Kumar, S. Meenakshi; Kumar, S.; Kumar, P. Synthesis and antimicrobial activity of some (3-phenyl-5-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones: new derivatives of 1,3,5-trisubstituted pyrazolines. Med. Chem. Res., 2013, 22(1), 433-439.
[http://dx.doi.org/10.1007/s00044-012-0045-7]
[76]
Desai, N.C.; Pandya, D.D.; Kotadiya, G.M.; Desai, P. Synthesis and characterization of novel benzimidazole bearing pyrazoline derivatives as potential antimicrobial agents. Med. Chem. Res., 2014, 23(3), 1474-1487.
[http://dx.doi.org/10.1007/s00044-013-0756-4]
[77]
Johnson, M.; Younglove, B.; Lee, L.; LeBlanc, R.; Holt, H., Jr; Hills, P.; Mackay, H.; Brown, T.; Mooberry, S.L.; Lee, M. Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4. Bioorg. Med. Chem. Lett., 2007, 17(21), 5897-5901.
[http://dx.doi.org/10.1016/j.bmcl.2007.07.105] [PMID: 17827004]
[78]
Yar, M.S.; Siddiqui, A.A.; Ali, M.A.; Murugan, V.; Chandrashekhar, R. Synthesis and cytotoxic activity of novel pyrazoline derivatives against human lung tumor cell line (A549). J. Chin. Chem. Soc. (Taipei), 2007, 54(1), 81-86.
[http://dx.doi.org/10.1002/jccs.200700014]
[79]
Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Gzella, A.; Lesyk, R. Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity. Eur. J. Med. Chem., 2009, 44(4), 1396-1404.
[http://dx.doi.org/10.1016/j.ejmech.2008.09.032] [PMID: 19000643]
[80]
Shaharyar, M.; Abdullah, M.M.; Bakht, M.A.; Majeed, J. Pyrazoline bearing benzimidazoles: Search for anticancer agent. Eur. J. Med. Chem., 2010, 45(1), 114-119.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.032] [PMID: 19883957]
[81]
Insuasty, B.; Tigreros, A.; Orozco, F.; Quiroga, J.; Abonía, R.; Nogueras, M.; Sanchez, A.; Cobo, J. Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents. Bioorg. Med. Chem., 2010, 18(14), 4965-4974.
[http://dx.doi.org/10.1016/j.bmc.2010.06.013] [PMID: 20594863]
[82]
Banday, A.H.; Mir, B.P.; Lone, I.H.; Suri, K.A.; Kumar, H.M.S. Studies on novel D-ring substituted steroidal pyrazolines as potential anticancer agents. Steroids, 2010, 75(12), 805-809.
[http://dx.doi.org/10.1016/j.steroids.2010.02.014] [PMID: 20206644]
[83]
Parekh, S.; Bhavsar, D.; Savant, M.; Thakrar, S.; Bavishi, A.; Parmar, M.; Vala, H.; Radadiya, A.; Pandya, N.; Serly, J.; Molnár, J.; Shah, A. Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro. Eur. J. Med. Chem., 2011, 46(5), 1942-1948.
[http://dx.doi.org/10.1016/j.ejmech.2011.02.045] [PMID: 21396744]
[84]
Insuasty, B.; García, A.; Quiroga, J.; Abonia, R.; Ortiz, A.; Nogueras, M.; Cobo, J. Efficient microwave-assisted synthesis and antitumor activity of novel 4,4′-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols]. Eur. J. Med. Chem., 2011, 46(6), 2436-2440.
[http://dx.doi.org/10.1016/j.ejmech.2011.03.028] [PMID: 21481989]
[85]
Lee, M.; Brockway, O.; Dandavati, A.; Tzou, S.; Sjoholm, R.; Satam, V.; Westbrook, C.; Mooberry, S.L.; Zeller, M.; Babu, B.; Lee, M. A novel class of trans-methylpyrazoline analogs of combretastatins: Synthesis and in-vitro biological testing. Eur. J. Med. Chem., 2011, 46(7), 3099-3104.
[http://dx.doi.org/10.1016/j.ejmech.2011.03.064] [PMID: 21524832]
[86]
Khalil, N.A.; Ahmed, E.M.; El-Nassan, H.B. Synthesis, characterization, and biological evaluation of certain 1,3-thiazolone derivatives bearing pyrazoline moiety as potential anti-breast cancer agents. Med. Chem. Res., 2013, 22(2), 1021-1027.
[http://dx.doi.org/10.1007/s00044-012-0098-7]
[87]
Bai, X.; Shi, W.Q.; Chen, H.F.; Zhang, P.; Li, Y.; Yin, S.F. Synthesis and antitumor activity of 1-acetyl-3-(4-phenyl)-4,5-dihydro-2-pyrazoline-5-phenylursolate and 4-chalcone ursolate derivatives. Chem. Nat. Compd., 2012, 48(1), 60-65.
[http://dx.doi.org/10.1007/s10600-012-0159-7]
[88]
Abdel-Aziz, M.; Aly, O.M.; Khan, S.S.; Mukherjee, K.; Bane, S. Synthesis, cytotoxic properties and tubulin polymerization inhibitory activity of novel 2-pyrazoline derivatives. Arch. Pharm. (Weinheim), 2012, 345(7), 535-548.
[http://dx.doi.org/10.1002/ardp.201100471] [PMID: 22592968]
[89]
Insuasty, B.; Chamizo, L.; Muñoz, J.; Tigreros, A.; Quiroga, J.; Abonía, R.; Nogueras, M.; Cobo, J. Synthesis of 1-substituted 3-aryl-5-aryl(hetaryl)-2-pyrazolines and study of their antitumor activity. Arch. Pharm. (Weinheim), 2012, 345(4), 275-286.
[http://dx.doi.org/10.1002/ardp.201100170] [PMID: 22105771]
[90]
Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Day, C.W.; Smee, D.F.; Grellier, P.; Lesyk, R. Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones. Eur. J. Med. Chem., 2013, 66, 228-237.
[http://dx.doi.org/10.1016/j.ejmech.2013.05.044] [PMID: 23811085]
[91]
Shin, S.Y.; Yoon, H.; Hwang, D.; Ahn, S.; Kim, D.W.; Koh, D.; Lee, Y.H.; Lim, Y. Benzochalcones bearing pyrazoline moieties show anti-colorectal cancer activities and selective inhibitory effects on aurora kinases. Bioorg. Med. Chem., 2013, 21(22), 7018-7024.
[http://dx.doi.org/10.1016/j.bmc.2013.09.014] [PMID: 24095020]
[92]
Awadallah, F.M.; Piazza, G.A.; Gary, B.D.; Keeton, A.B.; Canzoneri, J.C. Synthesis of some dihydropyrimidine-based compounds bearing pyrazoline moiety and evaluation of their antiproliferative activity. Eur. J. Med. Chem., 2013, 70, 273-279.
[http://dx.doi.org/10.1016/j.ejmech.2013.10.003] [PMID: 24161704]
[93]
Rathore, P.; Yaseen, S.; Ovais, S.; Bashir, R.; Yaseen, R.; Hameed, A.D.; Samim, M.; Gupta, R.; Hussain, F.; Javed, K. Synthesis and evaluation of some new pyrazoline substituted benzenesulfonylureas as potential antiproliferative agents. Bioorg. Med. Chem. Lett., 2014, 24(7), 1685-1691.
[http://dx.doi.org/10.1016/j.bmcl.2014.02.059] [PMID: 24630557]
[94]
Shaharyar, M.; Siddiqui, A.A.; Ali, M.A.; Sriram, D.; Yogeeswari, P. Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines. Bioorg. Med. Chem. Lett., 2006, 16(15), 3947-3949.
[http://dx.doi.org/10.1016/j.bmcl.2006.05.024] [PMID: 16725324]
[95]
Ali, M.A.; Shaharyar, M.; Siddiqui, A.A. Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives. Eur. J. Med. Chem., 2007, 42(2), 268-275.
[http://dx.doi.org/10.1016/j.ejmech.2006.08.004] [PMID: 17007966]
[96]
Kasabe, A.J.; Kasabe, P.J. Synthesis, anti-tubercular and analgesic activity evaluation of new 3-pyrazoline derivatives. Int. J. Pharm. Pharm. Sci., 2010, 2, 132-135.
[97]
Sivakumar, P.M.; Prabhu Seenivasan, S.; Kumar, V.; Doble, M. Novel 1,3,5-triphenyl-2-pyrazolines as anti-infective agents. Bioorg. Med. Chem. Lett., 2010, 20(10), 3169-3172.
[http://dx.doi.org/10.1016/j.bmcl.2010.03.083] [PMID: 20385494]
[98]
Khudina, O.G.; Burgart, Y.V.; Saloutin, V.I.; Kravchenkob, M.A. One-pot synthesis of trifluoromethyl- and nitroso-substituted pyrazolines and pyrazoles and their tuberculostatic activity. Russ. Chem. Bull., 2010, 59(10), 1967-1973.
[http://dx.doi.org/10.1007/s11172-010-0341-7]
[99]
Taj, T.; Kamble, R.R.; Gireesh, T.M.; Hunnur, R.K.; Margankop, S.B. One-pot synthesis of pyrazoline derivatised carbazoles as antitubercular, anticancer agents, their DNA cleavage and antioxidant activities. Eur. J. Med. Chem., 2011, 46(9), 4366-4373.
[http://dx.doi.org/10.1016/j.ejmech.2011.07.007] [PMID: 21802797]
[100]
Manna, K.; Agrawal, Y.K. Potent in vitro and in vivo antitubercular activity of certain newly synthesized indophenazine 1,3,5-trisubstituted pyrazoline derivatives bearing benzofuran. Med. Chem. Res., 2011, 20(3), 300-306.
[http://dx.doi.org/10.1007/s00044-010-9322-5]
[101]
Husain, K.; Abid, M.; Azam, A. Novel Pd(II) complexes of 1-N-substituted 3-phenyl-2-pyrazoline derivatives and evaluation of antiamoebic activity. Eur. J. Med. Chem., 2008, 43(2), 393-403.
[http://dx.doi.org/10.1016/j.ejmech.2007.03.021] [PMID: 17513021]
[102]
Abid, M.; Bhat, A.R.; Athar, F.; Azam, A. Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines. Eur. J. Med. Chem., 2009, 44(1), 417-425.
[http://dx.doi.org/10.1016/j.ejmech.2007.10.032] [PMID: 18068873]
[103]
Bhat, A.R.; Athar, F.; Azam, A. Bis-pyrazolines: Synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica. Eur. J. Med. Chem., 2009, 44(1), 426-431.
[http://dx.doi.org/10.1016/j.ejmech.2007.11.005] [PMID: 18187238]
[104]
Hayat, F.; Salahuddin, A.; Umar, S.; Azam, A. Synthesis, characterization, antiamoebic activity and cytotoxicity of novel series of pyrazoline derivatives bearing quinoline tail. Eur. J. Med. Chem., 2010, 45(10), 4669-4675.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.028] [PMID: 20696501]
[105]
Adhikari, N.; Maiti, M.K.; Jha, T. Exploring structural requirements of 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines as antiamoebic agents using comparative QSAR modelling. Bioorg. Med. Chem. Lett., 2010, 20(14), 4021-4026.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.098] [PMID: 20561784]
[106]
Mbarki, S.; Dguigui, K.; Hallaoui, M.E. Construction of 3D-QSAR models to predict antiamoebic activities of pyrazoline and dioxazoles derivatives. J. Mater. Environ. Sci., 2011, 2, 61-70.
[107]
Singh, P.; Negi, J.S.; Rawat, M.S.M. nee Pant, G.J. Synthesis, antiamoebic activity and thermal study of copper complexes of 1-formyl-2-pyrazolines. J. Therm. Anal. Calorim., 2013, 111(1), 549-552.
[http://dx.doi.org/10.1007/s10973-011-2168-3]
[108]
Du, X.; Guo, C.; Hansell, E.; Doyle, P.S.; Caffrey, C.R.; Holler, T.P.; McKerrow, J.H.; Cohen, F.E. Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain. J. Med. Chem., 2002, 45(13), 2695-2707.
[http://dx.doi.org/10.1021/jm010459j] [PMID: 12061873]
[109]
Rizvi, S.U.F.; Siddiqui, H.L.; Ahmad, M.N.; Ahmad, M.; Bukhari, M.H. Novel quinolyl-thienyl chalcones and their 2-pyrazoline derivatives with diverse substitution pattern as antileishmanial agents against Leishmania major. Med. Chem. Res., 2012, 21(7), 1322-1333.
[http://dx.doi.org/10.1007/s00044-011-9647-8]
[110]
Havrylyuk, D.; Zimenkovsky, B.; Karpenko, O.; Grellier, P.; Lesyk, R. Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity. Eur. J. Med. Chem., 2014, 85, 245-254.
[http://dx.doi.org/10.1016/j.ejmech.2014.07.103] [PMID: 25089808]
[111]
Cunico, W.; Cechinel, C.A.; Bonacorso, H.G.; Martins, M.A.P.; Zanatta, N.; de Souza, M.V.N.; Freitas, I.O.; Soares, R.P.P.; Krettli, A.U. Antimalarial activity of 4-(5-trifluoromethyl-1H-pyrazol-1-yl)-chloroquine analogues. Bioorg. Med. Chem. Lett., 2006, 16(3), 649-653.
[http://dx.doi.org/10.1016/j.bmcl.2005.10.033] [PMID: 16257205]
[112]
Acharya, B.N.; Saraswat, D.; Tiwari, M.; Shrivastava, A.K.; Ghorpade, R.; Bapna, S.; Kaushik, M.P. Synthesis and antimalarial evaluation of 1, 3, 5-trisubstituted pyrazolines. Eur. J. Med. Chem., 2010, 45(2), 430-438.
[http://dx.doi.org/10.1016/j.ejmech.2009.10.023] [PMID: 19926176]
[113]
Wanare, G.; Aher, R.; Kawathekar, N.; Ranjan, R.; Kaushik, N.K.; Sahal, D. Synthesis of novel α-pyranochalcones and pyrazoline derivatives as Plasmodium falciparum growth inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(15), 4675-4678.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.069] [PMID: 20576433]
[114]
Aher, R.B.; Wanare, G.; Kawathekar, N.; Kumar, R.R.; Kaushik, N.K.; Sahal, D.; Chauhan, V.S. Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors. Bioorg. Med. Chem. Lett., 2011, 21(10), 3034-3036.
[http://dx.doi.org/10.1016/j.bmcl.2011.03.037] [PMID: 21493068]
[115]
Insuasty, B.; Montoya, A.; Becerra, D.; Quiroga, J.; Abonia, R.; Robledo, S.; Vélez, I.D.; Upegui, Y.; Nogueras, M.; Cobo, J. Synthesis of novel analogs of 2-pyrazoline obtained from [(7-chloroquinolin-4-yl)amino]chalcones and hydrazine as potential antitumor and antimalarial agents. Eur. J. Med. Chem., 2013, 67, 252-262.
[http://dx.doi.org/10.1016/j.ejmech.2013.06.049] [PMID: 23871905]
[116]
Karad, S.C.; Purohit, V.B.; Raval, D.K. Design, synthesis and characterization of fluoro substituted novel pyrazolylpyrazolines scaffold and their pharmacological screening. Eur. J. Med. Chem., 2014, 84, 51-58.
[http://dx.doi.org/10.1016/j.ejmech.2014.07.008] [PMID: 25016227]
[117]
Goodell, J.R.; Puig-Basagoiti, F.; Forshey, B.M.; Shi, P.Y.; Ferguson, D.M. Identification of compounds with anti-West Nile Virus activity. J. Med. Chem., 2006, 49(6), 2127-2137.
[http://dx.doi.org/10.1021/jm051229y] [PMID: 16539402]
[118]
Ramajayam, R.; Tan, K.P.; Liu, H.G.; Liang, P.H. Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors. Bioorg. Med. Chem., 2010, 18(22), 7849-7854.
[http://dx.doi.org/10.1016/j.bmc.2010.09.050] [PMID: 20947359]
[119]
Rizvi, S.U.F.; Siddiqui, H.L.; Johns, M.; Detorio, M.; Schinazi, R.F. Anti-HIV-1 and cytotoxicity studies of piperidyl-thienyl chalcones and their 2-pyrazoline derivatives. Med. Chem. Res., 2012, 21(11), 3741-3749.
[http://dx.doi.org/10.1007/s00044-011-9912-x]
[120]
Jeong, T.S.; Soon Kim, K.; An, S.J.; Cho, K.H.; Lee, S.; Song, Lee W. Novel 3,5-diaryl pyrazolines as human acyl-CoA:cholesterol acyltransferase inhibitors. Bioorg. Med. Chem. Lett., 2004, 14(11), 2715-2717.
[http://dx.doi.org/10.1016/j.bmcl.2004.03.079] [PMID: 15125920]
[121]
Meyers, M.J.; Arhancet, G.B.; Hockerman, S.L.; Chen, X.; Long, S.A.; Mahoney, M.W.; Rico, J.R.; Garland, D.J.; Blinn, J.R.; Collins, J.T.; Yang, S.; Huang, H.C.; McGee, K.F.; Wendling, J.M.; Dietz, J.D.; Payne, M.A.; Homer, B.L.; Heron, M.I.; Reitz, D.B.; Hu, X. Discovery of (3S,3aR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid (PF-3882845), an orally efficacious mineralocorticoid receptor (MR) antagonist for hypertension and nephropathy. J. Med. Chem., 2010, 53(16), 5979-6002.
[http://dx.doi.org/10.1021/jm100505n] [PMID: 20672822]
[122]
Casimiro-Garcia, A.; Piotrowski, D.W.; Ambler, C.; Arhancet, G.B.; Banker, M.E.; Banks, T.; Boustany-Kari, C.M.; Cai, C.; Chen, X.; Eudy, R.; Hepworth, D.; Hulford, C.A.; Jennings, S.M.; Loria, P.M.; Meyers, M.J.; Petersen, D.N.; Raheja, N.K.; Sammons, M.; She, L.; Song, K.; Vrieze, D.; Wei, L. Identification of (R)-6-(1-(4-cyano-3-methylphenyl)-5-cyclopentyl-4,5-dihydro-1H-pyrazol-3-yl)-2-methoxynicotinic acid, a highly potent and selective nonsteroidal mineralocorticoid receptor antagonist. J. Med. Chem., 2014, 57(10), 4273-4288.
[http://dx.doi.org/10.1021/jm500206r] [PMID: 24738581]
[123]
Siddiqui, A.A.; Rahman, M.A.; Shaharyar, M.; Mishra, R. Synthesis and anticonvulsant activity of some substituted 3,5-diphenyl-2-pyrazoline-1-carboxamide derivatives. Chem. Sci. J., 2010, 1(1), 1-10.
[http://dx.doi.org/10.4172/2150-3494.1000006]
[124]
Aboul-Enein, M.N.; El-Azzouny, A.A.; Attia, M.I.; Maklad, Y.A.; Amin, K.M.; Abdel-Rehim, M.; El-Behairy, M.F. Design and synthesis of novel stiripentol analogues as potential anticonvulsants. Eur. J. Med. Chem., 2012, 47(1), 360-369.
[http://dx.doi.org/10.1016/j.ejmech.2011.11.004] [PMID: 22118828]
[125]
Özdemir, Z.; Kandilci, H.B.; Gümüşel, B.; Çalış, Ü.; Bilgin, A.A. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur. J. Med. Chem., 2007, 42(3), 373-379.
[http://dx.doi.org/10.1016/j.ejmech.2006.09.006] [PMID: 17069933]
[126]
Can, Ö.D.; Özkay, Ü.D.; Kaplancıklı, Z.A.; Öztürk, Y. Effects of some 1,3,5-trisubstitued-2-pyrazoline derivatives on depression and anxiety parameters of mice. Arch. Pharm. Res., 2009, 32(9), 1293-1299.
[http://dx.doi.org/10.1007/s12272-009-1915-5] [PMID: 19784586]
[127]
Gok, S.; Murat Demet, M.; Özdemir, A.; Turan-Zitouni, G. Evaluation of antidepressant-like effect of 2-pyrazoline derivatives. Med. Chem. Res., 2010, 19(1), 94-101.
[http://dx.doi.org/10.1007/s00044-009-9176-x]
[128]
Kaplancıklı, Z.A.; Özdemir, A.; Turan-Zitouni, G.; Altıntop, M.D.; Can, Ö.D. New pyrazoline derivatives and their antidepressant activity. Eur. J. Med. Chem., 2010, 45(9), 4383-4387.
[http://dx.doi.org/10.1016/j.ejmech.2010.06.011] [PMID: 20587366]
[129]
Abdel-Latif, N.A.; Sabry, N.M.; Mohamed, A.M.; Abdulla, M.M. Synthesis, analgesic, and antiparkinsonian profiles of some pyridine, pyrazoline, and thiopyrimidine derivatives. Monatsh. Chem., 2007, 138(7), 715-724.
[http://dx.doi.org/10.1007/s00706-007-0656-8]
[130]
van Loevezijn, A.; Venhorst, J.; Iwema Bakker, W.I.; de Korte, C.G.; de Looff, W.; Verhoog, S.; van Wees, J.W.; van Hoeve, M.; van de Woestijne, R.P.; van der Neut, M.A.W.; Borst, A.J.M.; van Dongen, M.J.P.; de Bruin, N.M.W.J.; Keizer, H.G.; Kruse, C.G. N ′-(arylsulfonyl)pyrazoline-1-carboxamidines as novel, neutral 5-hydroxytryptamine 6 receptor (5-HT₆R) antagonists with unique structural features. J. Med. Chem., 2011, 54(20), 7030-7054.
[http://dx.doi.org/10.1021/jm200466r] [PMID: 21866910]
[131]
Jayaprakash, V.; Sinha, B.N.; Ucar, G.; Ercan, A. Pyrazoline-based mycobactin analogues as MAO-inhibitors. Bioorg. Med. Chem. Lett., 2008, 18(24), 6362-6368.
[http://dx.doi.org/10.1016/j.bmcl.2008.10.084] [PMID: 18980841]
[132]
Gökhan-Kelekçi, N.; Koyunoğlu, S.; Yabanoğlu, S.; Yelekçi, K.; Özgen, Ö.; Uçar, G.; Erol, K.; Kendi, E.; Yeşilada, A. New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: Synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. Bioorg. Med. Chem., 2009, 17(2), 675-689.
[http://dx.doi.org/10.1016/j.bmc.2008.11.068] [PMID: 19091581]
[133]
Chimenti, F.; Carradori, S.; Secci, D.; Bolasco, A.; Bizzarri, B.; Chimenti, P.; Granese, A.; Yáñez, M.; Orallo, F. Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1 H)-pyrazole derivatives. Eur. J. Med. Chem., 2010, 45(2), 800-804.
[http://dx.doi.org/10.1016/j.ejmech.2009.11.003] [PMID: 19926363]
[134]
Karuppasamy, M.; Mahapatra, M.; Yabanoglu, S.; Ucar, G.; Sinha, B.N.; Basu, A.; Mishra, N.; Sharon, A.; Kulandaivelu, U.; Jayaprakash, V. Development of selective and reversible pyrazoline based MAO-A inhibitors: Synthesis, biological evaluation and docking studies. Bioorg. Med. Chem., 2010, 18(5), 1875-1881.
[http://dx.doi.org/10.1016/j.bmc.2010.01.043] [PMID: 20149663]
[135]
Fioravanti, R.; Bolasco, A.; Manna, F.; Rossi, F.; Orallo, F.; Yáñez, M.; Vitali, A.; Ortuso, F.; Alcaro, S. Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(22), 6479-6482.
[http://dx.doi.org/10.1016/j.bmcl.2010.09.061] [PMID: 20934874]
[136]
Sahu, N.K.; Sahu, S.; Kohli, D.V. Novel molecular targets for antimalarial drug development. Chem. Biol. Drug Des., 2008, 71(4), 287-297.
[http://dx.doi.org/10.1111/j.1747-0285.2008.00640.x] [PMID: 18298458]
[137]
Mishra, N.; Sasmal, D. Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation. Bioorg. Med. Chem. Lett., 2011, 21(7), 1969-1973.
[http://dx.doi.org/10.1016/j.bmcl.2011.02.030] [PMID: 21377879]
[138]
Jagrat, M.; Behera, J.; Yabanoglu, S.; Ercan, A.; Ucar, G.; Sinha, B.N.; Sankaran, V.; Basu, A.; Jayaprakash, V. Pyrazoline based MAO inhibitors: Synthesis, biological evaluation and SAR studies. Bioorg. Med. Chem. Lett., 2011, 21(14), 4296-4300.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.057] [PMID: 21680183]
[139]
Secci, D.; Bolasco, A.; Chimenti, P.; Carradori, S. The state of the art of pyrazole derivatives as monoamine oxidase inhibitors and antidepressant/anticonvulsant agents. Curr. Med. Chem., 2011, 18(33), 5114-5144.
[http://dx.doi.org/10.2174/092986711797636090] [PMID: 22050759]
[140]
Das, N.; Dash, B.; Dhanawat, M.; Shrivastava, S. Design, synthesis, preliminary pharmacological evaluation, and docking studies of pyrazoline derivatives. Chem. Pap., 2012, 66(1), 67-74.
[http://dx.doi.org/10.2478/s11696-011-0106-2]
[141]
Jun, M.A.; Park, W.S.; Kang, S.K.; Kim, K.Y.; Kim, K.R.; Rhee, S.D.; Bae, M.A.; Kang, N.S.; Sohn, S.K.; Kim, S.G.; Lee, J.O.; Lee, D.H.; Cheon, H.G.; Kim, S.S.; Ahn, J.H. Synthesis and biological evaluation of pyrazoline analogues with β-amino acyl group as dipeptidyl peptidase IV inhibitors. Eur. J. Med. Chem., 2008, 43(9), 1889-1902.
[http://dx.doi.org/10.1016/j.ejmech.2007.11.029] [PMID: 18243422]
[142]
Lange, J.H.M.; van der Neut, M.A.W.; den Hartog, A.P.; Wals, H.C.; Hoogendoorn, J.; van Stuivenberg, H.H.; van Vliet, B.J.; Kruse, C.G. Synthesis, SAR and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles as potent cannabinoid CB1 receptor antagonists. Bioorg. Med. Chem. Lett., 2010, 20(5), 1752-1757.
[http://dx.doi.org/10.1016/j.bmcl.2010.01.049] [PMID: 20137935]
[143]
Lange, J.H.M.; Coolen, H.K.A.C.; van der Neut, M.A.W.; Borst, A.J.M.; Stork, B.; Verveer, P.C.; Kruse, C.G. Design, synthesis, biological properties, and molecular modeling investigations of novel tacrine derivatives with a combination of acetylcholinesterase inhibition and cannabinoid CB1 receptor antagonism. J. Med. Chem., 2010, 53(3), 1338-1346.
[http://dx.doi.org/10.1021/jm901614b] [PMID: 20047331]
[144]
Khalilullah, H.; Khan, S.; Ahsan, M.J.; Ahmed, B. Synthesis and antihepatotoxic activity of 5-(2,3-dihydro-1,4-benzodioxane-6-yl)-3-substituted-phenyl-4,5-dihydro-1H-pyrazole derivatives. Bioorg. Med. Chem. Lett., 2011, 21(24), 7251-7254.
[http://dx.doi.org/10.1016/j.bmcl.2011.10.056] [PMID: 22061643]
[145]
Sahoo, A.; Yabanoglu, S.; Sinha, B.N.; Ucar, G.; Basu, A.; Jayaprakash, V. Towards development of selective and reversible pyrazoline based MAO-inhibitors: Synthesis, biological evaluation and docking studies. Bioorg. Med. Chem. Lett., 2010, 20(1), 132-136.
[http://dx.doi.org/10.1016/j.bmcl.2009.11.015] [PMID: 19945874]
[146]
Singh, K.; Kaur, H.; Chibale, K.; Balzarini, J. Synthesis of 4-aminoquinoline–pyrimidine hybrids as potent antimalarials and their mode of action studies. Eur. J. Med. Chem., 2013, 66, 314-323.
[http://dx.doi.org/10.1016/j.ejmech.2013.05.046] [PMID: 23811093]
[147]
Varghese, B.; Al-Busafi, S.N.; Suliman, F.O.; Al-Kindy, S.M.Z. Unveiling a versatile heterocyclic: Pyrazoline–a review. RSC Advances, 2017, 7(74), 46999-47016.

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