Abstract
Heterocyclic compounds are amongst the most promising and versatile classes of biologically important molecules. One of the heterocycle molecules is pyrazole with a five-membered heterocyclic ring with two neighboring nitrogen. Pyrazole and its derivatives have shown a broad range of biological applications like antibacterial, antifungal, antiviral, anti-inflammatory, anti-cancerous, and herbicidal activities. The study of synthetic routes suggests three broad ways: cyclo-condensation of hydrazine and its derivatives on 1,3 difunctional systems, dipolar cycloadditions, and multicomponent reactions. The synthesis of pyrazoles involves the usage of a conventional catalyst and more progressive and efficient nanoparticles as catalysts. The use of nanocatalysts is grabbing the attention of researchers owing to their more efficacy and reproducibility, low cost, reusability, ease of production, etc. The current review is an epigrammatic study on the importance of pyrazole as a biologically important moiety, recent advances in the three aforementioned routes to synthesize pyrazole and its derivatives, and a brief on the importance of nanocatalysts.
Graphical Abstract
[http://dx.doi.org/10.1016/j.mam.2005.07.008] [PMID: 16105678]
[http://dx.doi.org/10.3389/fphar.2021.666725] [PMID: 34040529]
[http://dx.doi.org/10.3109/14756366.2015.1057717] [PMID: 26114308]
[http://dx.doi.org/10.1016/j.ejmech.2019.111893] [PMID: 31761383]
[http://dx.doi.org/10.1016/j.phytochem.2008.08.013] [PMID: 18834606]
[http://dx.doi.org/10.1021/jm070528f] [PMID: 17894480]
[http://dx.doi.org/10.1016/j.bmcl.2015.10.028] [PMID: 26490095]
[http://dx.doi.org/10.1016/j.ejmech.2015.07.002] [PMID: 26186150]
[http://dx.doi.org/10.1111/cbdd.12336] [PMID: 24720475]
[http://dx.doi.org/10.1007/s00044-011-9606-4]
[http://dx.doi.org/10.1016/j.bioorg.2017.08.014] [PMID: 28865292]
[http://dx.doi.org/10.1016/j.bmcl.2005.08.040] [PMID: 16168645]
[http://dx.doi.org/10.1016/j.ejmech.2006.09.006] [PMID: 17069933]
[http://dx.doi.org/10.1021/jm960444z] [PMID: 8831758]
[http://dx.doi.org/10.1002/jhet.5570390503]
[http://dx.doi.org/10.1021/jm5002937] [PMID: 24818517]
[http://dx.doi.org/10.1016/j.ejmech.2011.12.013] [PMID: 22204901]
[http://dx.doi.org/10.1002/ps.3918] [PMID: 25256846]
[http://dx.doi.org/10.1021/cr200427q] [PMID: 22548590]
[http://dx.doi.org/10.1016/j.ejmech.2014.11.059] [PMID: 25555743]
[http://dx.doi.org/10.2165/00044011-200828070-00003] [PMID: 18544002]
[http://dx.doi.org/10.3109/14756366.2015.1094469] [PMID: 26482802]
[http://dx.doi.org/10.1016/j.ejmech.2014.07.052] [PMID: 25050881]
[http://dx.doi.org/10.1016/j.bmc.2013.11.038] [PMID: 24326275]
[http://dx.doi.org/10.1039/C5OB00258C] [PMID: 25765334]
[http://dx.doi.org/10.1016/j.bioorg.2018.02.018] [PMID: 29475165]
[http://dx.doi.org/10.1016/j.bmc.2018.07.022] [PMID: 30031652]
[http://dx.doi.org/10.1016/j.bmcl.2017.04.020] [PMID: 28427813]
[http://dx.doi.org/10.1021/jm960803q] [PMID: 9135032]
[http://dx.doi.org/10.1016/j.ejmech.2010.10.005] [PMID: 20974503]
[http://dx.doi.org/10.2174/138955709788452739] [PMID: 19519492]
[http://dx.doi.org/10.1016/j.ejmech.2009.04.009] [PMID: 19457595]
[http://dx.doi.org/10.3390/molecules15063958] [PMID: 20657419]
[PMID: 3743739]
[http://dx.doi.org/10.1155/2014/329681]
[http://dx.doi.org/10.1016/j.matchemphys.2018.09.080]
[http://dx.doi.org/10.1002/cber.188301602194]
[http://dx.doi.org/10.1021/cb0500042] [PMID: 17163639]
[http://dx.doi.org/10.1021/jm00354a018] [PMID: 6218302]
[http://dx.doi.org/10.1021/ja01585a023]
[http://dx.doi.org/10.1248/cpb.21.941] [PMID: 4727362]
[http://dx.doi.org/10.1021/jm0611915] [PMID: 17948975]
[http://dx.doi.org/10.1021/jm070566z] [PMID: 18293908]
[http://dx.doi.org/10.1002/(SICI)1096-9063(199708)50:4<324:AID-PS596>3.0.CO;2-D]
[http://dx.doi.org/10.1016/j.mrgentox.2012.05.014] [PMID: 22743356]
[http://dx.doi.org/10.1016/S0960-894X(00)00272-9] [PMID: 10999468]
[http://dx.doi.org/10.1016/S0014-827X(01)01098-9] [PMID: 11601645]
[http://dx.doi.org/10.1016/j.farmac.2004.09.003] [PMID: 15652364]
[http://dx.doi.org/10.1016/S0040-4039(02)02158-5]
[http://dx.doi.org/10.1016/j.bmc.2004.01.037] [PMID: 15051061]
[http://dx.doi.org/10.1016/j.bmcl.2006.09.008] [PMID: 17000107]
[http://dx.doi.org/10.1002/cmdc.200700218] [PMID: 17943713]
[http://dx.doi.org/10.2174/1389557511009011014] [PMID: 20540709]
[http://dx.doi.org/10.1016/j.ejmech.2007.03.030] [PMID: 17532544]
[http://dx.doi.org/10.1016/j.bmc.2008.09.070] [PMID: 18945621]
[http://dx.doi.org/10.1016/j.bmc.2010.05.034] [PMID: 20627597]
[http://dx.doi.org/10.1016/j.bmcl.2010.05.105] [PMID: 20594840]
[http://dx.doi.org/10.1016/j.bmc.2009.10.035] [PMID: 19896853]
[http://dx.doi.org/10.1016/j.ejmech.2009.07.004] [PMID: 19646797]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.004] [PMID: 20817327]
[http://dx.doi.org/10.1016/j.ejmech.2010.01.021] [PMID: 20144494]
[http://dx.doi.org/10.1039/C6NJ03181A]
[http://dx.doi.org/10.3390/molecules23010134] [PMID: 29329257]
[http://dx.doi.org/10.3390/biomedicines10051124] [PMID: 35625859]
[http://dx.doi.org/10.2174/1389557517666170927160919] [PMID: 28971774]
[http://dx.doi.org/10.1016/j.tet.2012.01.075]
[http://dx.doi.org/10.1055/s-2006-956487]
[http://dx.doi.org/10.1055/s-2003-44376]
[http://dx.doi.org/10.3390/molecules27165178] [PMID: 36014420]
[http://dx.doi.org/10.3390/cryst12081016]
[http://dx.doi.org/10.5267/j.ccl.2022.1.002]
[http://dx.doi.org/10.1080/00397911.2020.1801747]
[http://dx.doi.org/10.1080/00397911.2021.1958231]
[http://dx.doi.org/10.3987/REV-19-925]
[http://dx.doi.org/10.1021/acs.joc.1c02521] [PMID: 34913680]
[http://dx.doi.org/10.1055/s-0040-1707262]
[http://dx.doi.org/10.1021/ol3025154] [PMID: 23035910]
[http://dx.doi.org/10.1016/j.tetlet.2009.03.030]
[http://dx.doi.org/10.1016/j.tetlet.2009.07.152]
[http://dx.doi.org/10.1039/b311763d] [PMID: 14765225]
[http://dx.doi.org/10.1002/anie.200700069] [PMID: 17378008]
[http://dx.doi.org/10.1021/ol101087j] [PMID: 20597542]
[http://dx.doi.org/10.1021/acs.orglett.9b00860] [PMID: 30990050]
[http://dx.doi.org/10.1021/acs.orglett.1c01665] [PMID: 34097415]
[http://dx.doi.org/10.1021/jo4027116] [PMID: 24512630]
[http://dx.doi.org/10.1016/j.tet.2013.08.047]
[http://dx.doi.org/10.1021/jacs.9b13173] [PMID: 32043879]
[http://dx.doi.org/10.1021/acs.orglett.1c03879] [PMID: 34908420]
[http://dx.doi.org/10.1021/ol402810f] [PMID: 24255982]
[http://dx.doi.org/10.1021/acs.joc.8b02897] [PMID: 30714367]
[http://dx.doi.org/10.1021/acs.joc.3c00019] [PMID: 36947699]
[http://dx.doi.org/10.1021/acs.oprd.3c00056]
[http://dx.doi.org/10.1016/j.crci.2012.07.003]
[http://dx.doi.org/10.1021/acs.joc.3c00382] [PMID: 37125502]
[http://dx.doi.org/10.1021/acs.joc.1c01846] [PMID: 34747592]
[http://dx.doi.org/10.1021/acsomega.1c04773] [PMID: 34805701]
[http://dx.doi.org/10.14233/ajchem.2021.23196]
[http://dx.doi.org/10.1007/s11164-021-04450-6]
[http://dx.doi.org/10.1016/j.crgsc.2021.100134]
[http://dx.doi.org/10.1002/9781118287705.ch12]
[http://dx.doi.org/10.1016/j.arabjc.2017.09.016]
[http://dx.doi.org/10.1002/aoc.6409]
[http://dx.doi.org/10.1016/j.molstruc.2022.132713]
[http://dx.doi.org/10.1016/j.matpr.2020.06.283]
[http://dx.doi.org/10.5267/j.ccl.2021.4.006]
[http://dx.doi.org/10.1016/j.surfin.2021.101225]
[http://dx.doi.org/10.1016/j.jpcs.2021.110097]
[http://dx.doi.org/10.1016/j.molstruc.2022.132843]
[http://dx.doi.org/10.1002/aoc.6365]
[http://dx.doi.org/10.1007/s11164-022-04702-z]
[http://dx.doi.org/10.3390/molecules26123689] [PMID: 34204215]
[http://dx.doi.org/10.1016/j.ijbiomac.2021.08.085] [PMID: 34411618]
[http://dx.doi.org/10.1155/2021/1784142]
[http://dx.doi.org/10.1186/s13065-021-00734-5] [PMID: 33430936]
[http://dx.doi.org/10.1080/00397911.2020.1817941]
[http://dx.doi.org/10.1039/c3cy00344b]
[http://dx.doi.org/10.1039/D0NJ90154G]
[http://dx.doi.org/10.1002/aoc.5472]
[http://dx.doi.org/10.1134/S1070428020090249]
[http://dx.doi.org/10.1016/j.mcat.2018.09.018]
[http://dx.doi.org/10.1039/c3cy00901g]
[http://dx.doi.org/10.1039/C4GC02420F]
[http://dx.doi.org/10.1039/C5RA11343A]
[http://dx.doi.org/10.1080/00397911.2016.1171360]
[http://dx.doi.org/10.1016/j.arabjc.2017.11.006]
[http://dx.doi.org/10.1002/jccs.202000310]
[http://dx.doi.org/10.1007/s00706-013-1104-6]
[http://dx.doi.org/10.1021/cc900076j] [PMID: 19711896]
[http://dx.doi.org/10.6023/cjoc201803019]