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.
Graphical Abstract
[http://dx.doi.org/10.1016/j.arabjc.2011.09.013]
[http://dx.doi.org/10.2174/1389557511313060012] [PMID: 23544604]
[http://dx.doi.org/10.1016/j.ejmech.2013.04.044] [PMID: 23693151]
[http://dx.doi.org/10.1016/j.bfopcu.2013.04.002]
[http://dx.doi.org/10.1016/j.sjbs.2015.07.005] [PMID: 27579011]
[http://dx.doi.org/10.2174/1570178616666190212145754]
[http://dx.doi.org/10.1016/j.arabjc.2013.10.023]
[http://dx.doi.org/10.1002/ajoc.202100794]
[http://dx.doi.org/10.1021/ja01096a021]
[http://dx.doi.org/10.1039/jr9520004138]
[http://dx.doi.org/10.1021/ja01330a043]
[http://dx.doi.org/10.1016/j.bmcl.2013.02.105] [PMID: 23541672]
[http://dx.doi.org/10.1016/j.ejmech.2012.12.004] [PMID: 23291120]
[http://dx.doi.org/10.1016/j.bmc.2012.11.020] [PMID: 23245802]
[http://dx.doi.org/10.1016/j.bmc.2013.01.013] [PMID: 23391364]
[http://dx.doi.org/10.1007/s00044-013-0530-7]
[http://dx.doi.org/10.1016/j.bmc.2012.09.060] [PMID: 23177727]
[http://dx.doi.org/10.1002/jhet.2215]
[http://dx.doi.org/10.1016/j.jsps.2014.07.009] [PMID: 25972742]
[http://dx.doi.org/10.1016/j.ejmech.2014.04.046] [PMID: 24780598]
[http://dx.doi.org/10.1016/j.bmcl.2014.09.044] [PMID: 25442322]
[http://dx.doi.org/10.1002/jhet]
[http://dx.doi.org/10.1016/j.bmcl.2014.06.015] [PMID: 24986657]
[http://dx.doi.org/10.1016/j.bmcl.2014.07.085] [PMID: 25127869]
[http://dx.doi.org/10.1002/jhet.1646]
[http://dx.doi.org/10.1016/j.arabjc.2011.06.015]
[http://dx.doi.org/10.1007/s00044-014-0976-2]
[http://dx.doi.org/10.1021/jm500521n] [PMID: 25058929]
[http://dx.doi.org/10.1021/ol501249h] [PMID: 24850209]
[http://dx.doi.org/10.1002/jhet.1683]
[http://dx.doi.org/10.1016/j.bmc.2006.01.042] [PMID: 16460945]
[http://dx.doi.org/10.1016/j.ejmech.2008.09.002] [PMID: 18922604]
[http://dx.doi.org/10.1016/j.bmc.2008.01.047] [PMID: 18272371]
[http://dx.doi.org/10.4314/tjpr.v7i2.14664]
[http://dx.doi.org/10.1016/j.bmcl.2007.12.043] [PMID: 18182288]
[http://dx.doi.org/10.1016/j.bmcl.2008.10.105] [PMID: 19010670]
[http://dx.doi.org/10.1016/j.ejmech.2008.09.020] [PMID: 18986738]
[http://dx.doi.org/10.1016/j.ejmech.2010.01.059] [PMID: 20171763]
[http://dx.doi.org/10.1016/j.ejmech.2010.01.009] [PMID: 20149499]
[http://dx.doi.org/10.1016/j.ejmech.2010.10.005] [PMID: 20974503]
[http://dx.doi.org/10.1016/j.bmcl.2010.04.082] [PMID: 20529688]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.032] [PMID: 20702008]
[http://dx.doi.org/10.1016/j.ejmech.2011.08.015] [PMID: 22019186]
[http://dx.doi.org/10.1016/j.bmcl.2011.05.061] [PMID: 21664130]
[http://dx.doi.org/10.1111/j.1747-0285.2011.01076.x] [PMID: 21244639]
[http://dx.doi.org/10.1007/s00044-011-9619-z]
[http://dx.doi.org/10.1007/s00044-011-9735-9]
[http://dx.doi.org/10.1007/s00044-012-0130-y]
[http://dx.doi.org/10.1002/ardp.201200249] [PMID: 22961586]
[http://dx.doi.org/10.1016/j.bmcl.2013.06.042] [PMID: 23850201]
[http://dx.doi.org/10.1155/2009/361564]
[http://dx.doi.org/10.1016/j.bmc.2014.05.059] [PMID: 24934992]
[http://dx.doi.org/10.2478/s11696-008-0025-z]
[http://dx.doi.org/10.1021/jf802343p] [PMID: 18973342]
[http://dx.doi.org/10.1016/j.ejmech.2010.09.060] [PMID: 20970894]
[http://dx.doi.org/10.1016/j.ejmech.2009.10.015] [PMID: 19896247]
[http://dx.doi.org/10.1016/j.jscs.2011.02.012]
[http://dx.doi.org/10.1016/j.arabjc.2010.10.036]
[http://dx.doi.org/10.1016/j.jscs.2011.09.002]
[http://dx.doi.org/10.1002/ardp.201100077] [PMID: 21755528]
[http://dx.doi.org/10.1016/j.bmcl.2011.03.080] [PMID: 21507638]
[http://dx.doi.org/10.1007/s00044-012-0377-3]
[http://dx.doi.org/10.1007/s00044-011-9871-2]
[http://dx.doi.org/10.1111/j.1747-0285.2011.01308.x] [PMID: 22181692]
[http://dx.doi.org/10.1016/j.ejmech.2012.03.023] [PMID: 22480494]
[http://dx.doi.org/10.1007/s00044-012-0045-7]
[http://dx.doi.org/10.1007/s00044-013-0756-4]
[http://dx.doi.org/10.1016/j.bmcl.2007.07.105] [PMID: 17827004]
[http://dx.doi.org/10.1002/jccs.200700014]
[http://dx.doi.org/10.1016/j.ejmech.2008.09.032] [PMID: 19000643]
[http://dx.doi.org/10.1016/j.ejmech.2009.09.032] [PMID: 19883957]
[http://dx.doi.org/10.1016/j.bmc.2010.06.013] [PMID: 20594863]
[http://dx.doi.org/10.1016/j.steroids.2010.02.014] [PMID: 20206644]
[http://dx.doi.org/10.1016/j.ejmech.2011.02.045] [PMID: 21396744]
[http://dx.doi.org/10.1016/j.ejmech.2011.03.028] [PMID: 21481989]
[http://dx.doi.org/10.1016/j.ejmech.2011.03.064] [PMID: 21524832]
[http://dx.doi.org/10.1007/s00044-012-0098-7]
[http://dx.doi.org/10.1007/s10600-012-0159-7]
[http://dx.doi.org/10.1002/ardp.201100471] [PMID: 22592968]
[http://dx.doi.org/10.1002/ardp.201100170] [PMID: 22105771]
[http://dx.doi.org/10.1016/j.ejmech.2013.05.044] [PMID: 23811085]
[http://dx.doi.org/10.1016/j.bmc.2013.09.014] [PMID: 24095020]
[http://dx.doi.org/10.1016/j.ejmech.2013.10.003] [PMID: 24161704]
[http://dx.doi.org/10.1016/j.bmcl.2014.02.059] [PMID: 24630557]
[http://dx.doi.org/10.1016/j.bmcl.2006.05.024] [PMID: 16725324]
[http://dx.doi.org/10.1016/j.ejmech.2006.08.004] [PMID: 17007966]
[http://dx.doi.org/10.1016/j.bmcl.2010.03.083] [PMID: 20385494]
[http://dx.doi.org/10.1007/s11172-010-0341-7]
[http://dx.doi.org/10.1016/j.ejmech.2011.07.007] [PMID: 21802797]
[http://dx.doi.org/10.1007/s00044-010-9322-5]
[http://dx.doi.org/10.1016/j.ejmech.2007.03.021] [PMID: 17513021]
[http://dx.doi.org/10.1016/j.ejmech.2007.10.032] [PMID: 18068873]
[http://dx.doi.org/10.1016/j.ejmech.2007.11.005] [PMID: 18187238]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.028] [PMID: 20696501]
[http://dx.doi.org/10.1016/j.bmcl.2010.05.098] [PMID: 20561784]
[http://dx.doi.org/10.1007/s10973-011-2168-3]
[http://dx.doi.org/10.1021/jm010459j] [PMID: 12061873]
[http://dx.doi.org/10.1007/s00044-011-9647-8]
[http://dx.doi.org/10.1016/j.ejmech.2014.07.103] [PMID: 25089808]
[http://dx.doi.org/10.1016/j.bmcl.2005.10.033] [PMID: 16257205]
[http://dx.doi.org/10.1016/j.ejmech.2009.10.023] [PMID: 19926176]
[http://dx.doi.org/10.1016/j.bmcl.2010.05.069] [PMID: 20576433]
[http://dx.doi.org/10.1016/j.bmcl.2011.03.037] [PMID: 21493068]
[http://dx.doi.org/10.1016/j.ejmech.2013.06.049] [PMID: 23871905]
[http://dx.doi.org/10.1016/j.ejmech.2014.07.008] [PMID: 25016227]
[http://dx.doi.org/10.1021/jm051229y] [PMID: 16539402]
[http://dx.doi.org/10.1016/j.bmc.2010.09.050] [PMID: 20947359]
[http://dx.doi.org/10.1007/s00044-011-9912-x]
[http://dx.doi.org/10.1016/j.bmcl.2004.03.079] [PMID: 15125920]
[http://dx.doi.org/10.1021/jm100505n] [PMID: 20672822]
[http://dx.doi.org/10.1021/jm500206r] [PMID: 24738581]
[http://dx.doi.org/10.4172/2150-3494.1000006]
[http://dx.doi.org/10.1016/j.ejmech.2011.11.004] [PMID: 22118828]
[http://dx.doi.org/10.1016/j.ejmech.2006.09.006] [PMID: 17069933]
[http://dx.doi.org/10.1007/s12272-009-1915-5] [PMID: 19784586]
[http://dx.doi.org/10.1007/s00044-009-9176-x]
[http://dx.doi.org/10.1016/j.ejmech.2010.06.011] [PMID: 20587366]
[http://dx.doi.org/10.1007/s00706-007-0656-8]
[http://dx.doi.org/10.1021/jm200466r] [PMID: 21866910]
[http://dx.doi.org/10.1016/j.bmcl.2008.10.084] [PMID: 18980841]
[http://dx.doi.org/10.1016/j.bmc.2008.11.068] [PMID: 19091581]
[http://dx.doi.org/10.1016/j.ejmech.2009.11.003] [PMID: 19926363]
[http://dx.doi.org/10.1016/j.bmc.2010.01.043] [PMID: 20149663]
[http://dx.doi.org/10.1016/j.bmcl.2010.09.061] [PMID: 20934874]
[http://dx.doi.org/10.1111/j.1747-0285.2008.00640.x] [PMID: 18298458]
[http://dx.doi.org/10.1016/j.bmcl.2011.02.030] [PMID: 21377879]
[http://dx.doi.org/10.1016/j.bmcl.2011.05.057] [PMID: 21680183]
[http://dx.doi.org/10.2174/092986711797636090] [PMID: 22050759]
[http://dx.doi.org/10.2478/s11696-011-0106-2]
[http://dx.doi.org/10.1016/j.ejmech.2007.11.029] [PMID: 18243422]
[http://dx.doi.org/10.1016/j.bmcl.2010.01.049] [PMID: 20137935]
[http://dx.doi.org/10.1021/jm901614b] [PMID: 20047331]
[http://dx.doi.org/10.1016/j.bmcl.2011.10.056] [PMID: 22061643]
[http://dx.doi.org/10.1016/j.bmcl.2009.11.015] [PMID: 19945874]
[http://dx.doi.org/10.1016/j.ejmech.2013.05.046] [PMID: 23811093]