Abstract
Pyrazoles, an important and well-known class of the azole family, have been found to show a large number of applications in various fields, especially medicinal chemistry. Pyrazole derivatives, particularly methyl-substituted pyrazoles, have been reported as potent medicinal scaffolds that exhibit a wide spectrum of biological activities. The present review is an attempt to highlight the detailed synthetic approaches for methyl-substituted pyrazoles along with an in-depth analysis of their respective medical significances till March 2021. It is hoped that literature sum-up in the form of present review article would certainly be a great tool in assisting medicinal chemists in generating new leads possessing pyrazole nucleus with high efficacy and less microbial resistance.
Keywords: Pyrazoles, drug discovery, medicinal chemistry, organic synthesis, microbial resistance, NMR spectral characteristics.
Graphical Abstract
[http://dx.doi.org/10.1016/j.ejmech.2020.112066] [PMID: 31982653]
[http://dx.doi.org/10.1039/D0NJ02666B]
[http://dx.doi.org/10.1039/C6NJ03181A]
[http://dx.doi.org/10.1016/j.molstruc.2019.127625]
[http://dx.doi.org/10.4103/0975-7406.171694] [PMID: 26957862]
[http://dx.doi.org/10.1016/j.ejmech.2014.05.004] [PMID: 24849271]
[http://dx.doi.org/10.1007/s00044-014-1254-z]
[http://dx.doi.org/10.1007/s00044-015-1340-x]
[http://dx.doi.org/10.1002/jhet.3769]
[http://dx.doi.org/10.2174/1389557517666170927160919] [PMID: 28971774]
[http://dx.doi.org/10.2174/1872213X11307020004] [PMID: 23565678]
[http://dx.doi.org/10.1016/j.bmc.2017.09.035] [PMID: 28988624]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.032] [PMID: 20702008]
[http://dx.doi.org/10.1016/j.bmc.2005.10.026] [PMID: 16300953]
[http://dx.doi.org/10.1016/j.ejmech.2009.01.032] [PMID: 19268406]
[http://dx.doi.org/10.3390/molecules21010068] [PMID: 26760990]
[http://dx.doi.org/10.1007/s12039-019-1646-1]
[http://dx.doi.org/10.1016/j.ejmech.2013.08.053] [PMID: 24099993]
[http://dx.doi.org/10.6023/cjoc201701042]
[PMID: 21247401]
[http://dx.doi.org/10.1016/j.ejmech.2012.05.008] [PMID: 22683243]
[http://dx.doi.org/10.1021/jm030394f] [PMID: 15214796]
[http://dx.doi.org/10.1080/10406638.2019.1584576]
[http://dx.doi.org/10.1016/j.bmc.2004.03.069] [PMID: 15158803]
[http://dx.doi.org/10.1016/S0040-4039(01)99671-6] [PMID: 5905317]
[http://dx.doi.org/10.1016/S0140-6736(20)30304-4] [PMID: 32032529]
[http://dx.doi.org/10.1016/j.phytochem.2007.11.001] [PMID: 18086481]
[http://dx.doi.org/10.1016/j.tet.2008.06.014]
[http://dx.doi.org/10.1021/jm00152a016] [PMID: 3950908]
[http://dx.doi.org/10.1016/S0140-6736(07)60033-6] [PMID: 17208644]
[http://dx.doi.org/10.1111/j.1365-2125.1977.tb00710.x] [PMID: 332216]
[http://dx.doi.org/10.1007/s00044-009-9163-2]
[http://dx.doi.org/10.1016/j.phrs.2010.06.007] [PMID: 20600917]
[http://dx.doi.org/10.3390/molecules23010134] [PMID: 29329257]
[http://dx.doi.org/10.3390/molecules25051047] [PMID: 32110945]
[http://dx.doi.org/10.1002/slct.201900373]
[http://dx.doi.org/10.1098/rsos.172435] [PMID: 29892430]
[http://dx.doi.org/10.1016/j.bmc.2008.09.070] [PMID: 18945621]
[http://dx.doi.org/10.3390/molecules21010039] [PMID: 26712728]
[http://dx.doi.org/10.1016/j.ejmech.2014.01.018] [PMID: 24607998]
[http://dx.doi.org/10.1016/j.bmcl.2012.05.020] [PMID: 22658862]
[http://dx.doi.org/10.1016/j.ejmech.2008.09.006] [PMID: 18930566]
[http://dx.doi.org/10.1016/j.ejmech.2014.08.048] [PMID: 25147154]
[http://dx.doi.org/10.1016/j.ejmech.2014.02.033] [PMID: 24607877]
[http://dx.doi.org/10.1016/j.bmcl.2013.09.062] [PMID: 24125880]
[http://dx.doi.org/10.1016/j.ejmech.2010.05.049] [PMID: 20573423]
[http://dx.doi.org/10.1016/j.ejmech.2005.03.021] [PMID: 15921826]
[http://dx.doi.org/10.1016/j.bmcl.2004.09.066] [PMID: 15546724]
[http://dx.doi.org/10.1016/j.bmcl.2009.07.150] [PMID: 19703770]
[http://dx.doi.org/10.1016/j.jscs.2011.03.016]
[http://dx.doi.org/10.1186/s13065-019-0632-5] [PMID: 31572983]
[http://dx.doi.org/10.3389/fchem.2019.00917] [PMID: 32039146]
[http://dx.doi.org/10.1080/00397911.2017.1393687]
[http://dx.doi.org/10.5267/j.ccl.2021.3.003]
[http://dx.doi.org/10.1016/j.bmcl.2009.08.039] [PMID: 19709880]
[http://dx.doi.org/10.1016/j.ejmech.2013.10.072] [PMID: 24292338]
[http://dx.doi.org/10.1016/j.bmcl.2006.06.086] [PMID: 16843659]
[http://dx.doi.org/10.1016/j.bmcl.2007.07.101] [PMID: 17804224]
[http://dx.doi.org/10.1016/j.ejmech.2011.07.029] [PMID: 21839549]
[http://dx.doi.org/10.1007/s10593-020-02652-1]
[http://dx.doi.org/10.1016/j.ejmech.2018.08.053] [PMID: 30196060]
[http://dx.doi.org/10.1016/j.molstruc.2021.130231]
[http://dx.doi.org/10.1007/s00044-015-1452-3]
[http://dx.doi.org/10.1007/s00044-015-1429-2]
[http://dx.doi.org/10.1002/chin.200219140]
[http://dx.doi.org/10.1007/s00044-010-9358-6]
[http://dx.doi.org/10.5530/ijper.51.4.96]
[PMID: 24062119]
[http://dx.doi.org/10.1016/j.ejmech.2011.06.012] [PMID: 21723647]
[http://dx.doi.org/10.1016/j.jscs.2012.07.020]
[http://dx.doi.org/10.2478/v10007-009-0018-7] [PMID: 19564141]
[http://dx.doi.org/10.1016/j.ejmech.2013.12.010] [PMID: 24576591]
[http://dx.doi.org/10.2174/1573407212666161101152735]
[http://dx.doi.org/10.1016/j.cdc.2020.100408]
[http://dx.doi.org/10.1016/j.heliyon.2020.e03185] [PMID: 31956713]
[http://dx.doi.org/10.1016/j.bioorg.2021.104696] [PMID: 33652343]
[http://dx.doi.org/10.1002/ardp.200400940] [PMID: 15864786]
[http://dx.doi.org/10.3390/app6010027]