Abstract
As nitrogen-containing five-membered heterocyclic structural units, the substituted pyrazole derivatives have a broad spectrum of pharmacological activities, especially 4,5-dihydro-1H-pyrazoles that also commonly known as 2-pyrazolines. Since 2010, considerable studies have been found that the 2-pyrazoline derivatives possess potent anticancer activities. In the present review, it covers the pyrazoline derivatives reported by literature from 2010 till date (2010-2019). This review aims to establish the relationship between the anticancer activities variation and different substituents introduced into a 2-pyrazoline core, which could provide important pharmacophore clues for the discovery of new anticancer agents containing 2-pyrazoline scaffold.
Keywords: 2-pyrazoline, 4, 5-dihydro-1H-pyrazole, derivatives, anticancer activities, synthesis, SAR, Nitrogencontaining heterocyclic structural units.
[http://dx.doi.org/10.1016/j.ejmech.2013.08.053] [PMID: 24099993]
[http://dx.doi.org/10.1021/ja201708f] [PMID: 21488638]
[http://dx.doi.org/10.1111/j.1747-0285.2011.01113.x] [PMID: 21352504]
[http://dx.doi.org/10.1016/j.tetlet.2011.12.055] [PMID: 22345825]
[http://dx.doi.org/10.1002/adsc.201500953]
[http://dx.doi.org/10.1021/ol502010g] [PMID: 25191696]
[http://dx.doi.org/10.1021/cr2000459] [PMID: 21806021]
[http://dx.doi.org/10.1021/ic701586c] [PMID: 18027932]
[http://dx.doi.org/10.1039/C7CC04610C] [PMID: 28707696]
[http://dx.doi.org/10.1021/jm960803q] [PMID: 9135032]
[http://dx.doi.org/10.1016/0960-894X(96)00323-X]
[http://dx.doi.org/10.1039/c39950001549]
[http://dx.doi.org/10.1016/j.arabjc.2011.09.013]
[http://dx.doi.org/10.1016/0006-2952(79)90651-8] [PMID: 110332]
[http://dx.doi.org/10.2174/157489109789318569] [PMID: 19545230]
[http://dx.doi.org/10.3109/14756366.2013.795956] [PMID: 23808806]
[http://dx.doi.org/10.1016/j.bmcl.2012.07.080] [PMID: 22901385]
[http://dx.doi.org/10.2174/1570179416666190703115133] [PMID: 31984913]
[http://dx.doi.org/10.4103/0250-474X.34569]
[http://dx.doi.org/10.1039/C6RA22705H]
[http://dx.doi.org/10.1007/s00044-013-0643-z]
[PMID: 12481383]
[http://dx.doi.org/10.1080/17415993.2010.497537]
[http://dx.doi.org/10.1155/2011/806854]
[http://dx.doi.org/10.1007/s00044-012-0377-3]
[http://dx.doi.org/10.1584/jpestics.D19-028] [PMID: 31530976]
[http://dx.doi.org/10.1007/s00044-015-1415-8]
[http://dx.doi.org/10.1002/ardp.19863190106] [PMID: 3008686]
[http://dx.doi.org/10.3390/molecules21080969] [PMID: 27472314]
[http://dx.doi.org/10.1007/s00044-011-9823-x]
[http://dx.doi.org/10.1155/2011/282061]
[http://dx.doi.org/10.1007/s00044-017-1963-1]
[http://dx.doi.org/10.1007/s00044-011-9912-x]
[http://dx.doi.org/10.1016/j.bmcl.2012.02.084] [PMID: 22444681]
[http://dx.doi.org/10.1007/s11164-017-3083-4]
[http://dx.doi.org/10.2174/15701808113109990055]
[http://dx.doi.org/10.1016/S0223-5234(00)90179-X] [PMID: 10960193]
[http://dx.doi.org/10.1002/ardp.200400935] [PMID: 15765490]
[http://dx.doi.org/10.1016/j.bmcl.2005.03.099] [PMID: 15911264]
[http://dx.doi.org/10.1002/ardp.201600285] [PMID: 28032664]
[http://dx.doi.org/10.1007/BF03245828]
[http://dx.doi.org/10.3390/molecules18032683] [PMID: 23449067]
[http://dx.doi.org/10.1111/j.1747-0285.2010.01020.x] [PMID: 20925692]
[http://dx.doi.org/10.1016/j.ejmech.2013.06.049] [PMID: 23871905]
[http://dx.doi.org/10.2174/1570178616666190212145754]
[http://dx.doi.org/10.1016/j.ejmech.2018.01.082] [PMID: 29499486]
[http://dx.doi.org/10.1007/s00044-013-0530-7]
[http://dx.doi.org/10.1016/j.ejmech.2006.09.006] [PMID: 17069933]
[PMID: 16149709]
[http://dx.doi.org/10.1016/j.ejmech.2010.10.005] [PMID: 20974503]
[http://dx.doi.org/10.1016/j.ejmech.2013.09.052] [PMID: 24177361]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.032] [PMID: 20702008]
[http://dx.doi.org/10.1016/j.ejmech.2008.07.008] [PMID: 18722034]
[http://dx.doi.org/10.1002/ardp.200300796] [PMID: 14677148]
[http://dx.doi.org/10.1016/j.bmcl.2017.06.063] [PMID: 28676270]
[http://dx.doi.org/10.1016/j.ejmech.2008.09.020] [PMID: 18986738]
[http://dx.doi.org/10.1016/j.taap.2019.114689] [PMID: 31344373]
[http://dx.doi.org/10.1007/s00044-018-2167-z]
[http://dx.doi.org/10.1007/s00044-009-9176-x]
[http://dx.doi.org/10.2174/1386207320666170504113158] [PMID: 28474547]
[http://dx.doi.org/10.1016/S0223-5234(00)01194-6] [PMID: 11248404]
[http://dx.doi.org/10.1016/j.ejmech.2008.09.032] [PMID: 19000643]
[http://dx.doi.org/10.1055/s-2004-831341]
[http://dx.doi.org/10.1080/14756360600703396] [PMID: 17194018]
[http://dx.doi.org/10.1007/s11164-012-0581-2]
[http://dx.doi.org/10.1055/s-0034-1378687]
[http://dx.doi.org/10.5935/0103-5053.20150084]
[http://dx.doi.org/10.1016/j.dnarep.2019.05.004] [PMID: 31176959]
[http://dx.doi.org/10.1016/0092-8674(95)90412-3] [PMID: 7834749]
[http://dx.doi.org/10.1007/s10495-013-0895-6] [PMID: 24002658]
[http://dx.doi.org/10.1111/acel.12951] [PMID: 30907059]
[http://dx.doi.org/10.1007/s13765-013-3065-1]
[http://dx.doi.org/10.1093/jnci/93.14.1062] [PMID: 11459867]
[http://dx.doi.org/10.1126/science.3798106] [PMID: 3798106]
[http://dx.doi.org/10.1038/35077225] [PMID: 11357143]
[http://dx.doi.org/10.1038/35052073] [PMID: 11252954]
[http://dx.doi.org/10.1006/excr.1999.4706] [PMID: 10579913]
[PMID: 7585629]
[http://dx.doi.org/10.1016/j.bmc.2010.05.034] [PMID: 20627597]
[http://dx.doi.org/10.1002/ardp.201100170] [PMID: 22105771]
[http://dx.doi.org/10.1038/s41598-018-21642-0] [PMID: 29459693]
[http://dx.doi.org/10.1016/j.biopha.2017.07.060] [PMID: 28750358]
[http://dx.doi.org/10.1248/bpb.b16-00277] [PMID: 27725438]
[http://dx.doi.org/10.1016/j.bmc.2013.01.013] [PMID: 23391364]
[http://dx.doi.org/10.3390/molecules22101635] [PMID: 28961210]
[http://dx.doi.org/10.1002/cmdc.201700690] [PMID: 29377564]
[http://dx.doi.org/10.1016/j.ejmech.2018.06.043] [PMID: 29940463]
[http://dx.doi.org/10.1016/j.bmcl.2011.05.061] [PMID: 21664130]
[http://dx.doi.org/10.1016/j.bioorg.2018.01.021] [PMID: 29427856]
[http://dx.doi.org/10.1371/journal.pone.0095702] [PMID: 24827980]
[http://dx.doi.org/10.3390/molecules23081956] [PMID: 30082588]
[http://dx.doi.org/10.1016/j.bmc.2010.07.037] [PMID: 20702096]
[http://dx.doi.org/10.3390/molecules16043410] [PMID: 21512449]
[http://dx.doi.org/10.1002/ardp.201100471] [PMID: 22592968]
[http://dx.doi.org/10.1007/s10600-012-0159-7]
[http://dx.doi.org/10.3390/molecules191118656] [PMID: 25405285]
[http://dx.doi.org/10.1002/jhet.1993]
[http://dx.doi.org/10.1016/j.bmc.2012.08.043] [PMID: 22985962]
[http://dx.doi.org/10.1016/j.bmcl.2016.09.076] [PMID: 27727127]
[http://dx.doi.org/10.1016/j.ejmech.2017.03.016] [PMID: 28329730]
[http://dx.doi.org/10.3390/app9081704]
[http://dx.doi.org/10.1016/j.ejmech.2018.12.030] [PMID: 30580241]
[http://dx.doi.org/10.1016/j.bmcl.2011.07.010] [PMID: 21802290]
[http://dx.doi.org/10.1016/j.bmc.2012.04.047] [PMID: 22583669]
[http://dx.doi.org/10.1002/jhet.1056]
[http://dx.doi.org/10.1016/j.ejmech.2019.111648] [PMID: 31493743]
[http://dx.doi.org/10.1021/acs.joc.7b02934] [PMID: 29268606]
[http://dx.doi.org/10.1007/s10870-011-0256-7]
[http://dx.doi.org/10.1039/C4NJ00594E]
[http://dx.doi.org/10.1016/j.steroids.2010.02.014] [PMID: 20206644]
[http://dx.doi.org/10.3109/14756366.2012.724682] [PMID: 23020635]
[http://dx.doi.org/10.1002/ardp.201400199] [PMID: 25139842]
[http://dx.doi.org/10.3390/molecules201019066] [PMID: 26492233]
[http://dx.doi.org/10.1002/cmdc.201600137] [PMID: 27159418]
[http://dx.doi.org/10.1016/j.ejps.2018.05.011] [PMID: 29772274]
[http://dx.doi.org/10.1016/j.molstruc.2018.03.004]
[http://dx.doi.org/10.1039/c3md00077j]
[http://dx.doi.org/10.1016/j.jscs.2012.05.004]
[http://dx.doi.org/10.1016/j.ejmech.2009.09.032] [PMID: 19883957]
[http://dx.doi.org/10.3109/14756366.2012.755623] [PMID: 23339428]
[http://dx.doi.org/10.1016/S0248-4900(01)01125-X] [PMID: 11730323]
[http://dx.doi.org/10.1016/S1535-6108(03)00189-2] [PMID: 12957284]
[http://dx.doi.org/10.1677/ERC-07-0085] [PMID: 18045949]
[http://dx.doi.org/10.3892/or_00000487] [PMID: 19724843]
[http://dx.doi.org/10.1016/j.bmc.2014.11.029] [PMID: 25496804]
[http://dx.doi.org/10.3390/molecules21070929] [PMID: 27438822]
[http://dx.doi.org/10.1186/s13065-018-0439-9] [PMID: 29926299]
[http://dx.doi.org/10.5935/0103-5053.20160166]
[http://dx.doi.org/10.3390/ijms17091499] [PMID: 27618013]
[http://dx.doi.org/10.1002/(SICI)1099-0690(200005)2000:9 <1773:AID-EJOC1773>3.0.CO;2-E]
[http://dx.doi.org/10.1021/ja056851u] [PMID: 16478146]
[http://dx.doi.org/10.1021/jo061838t] [PMID: 17221990]
[http://dx.doi.org/10.1002/hc.20666]
[http://dx.doi.org/10.1016/j.tet.2011.08.067]
[http://dx.doi.org/10.1016/j.ejmech.2011.07.058] [PMID: 21872366]
[http://dx.doi.org/10.1002/jhet.5570450134]
[http://dx.doi.org/10.1016/j.bmcl.2016.05.038] [PMID: 27234147]
[http://dx.doi.org/10.1021/acscombsci.7b00091] [PMID: 28723092]
[http://dx.doi.org/10.1038/nn.2360] [PMID: 19701198]
[http://dx.doi.org/10.1038/nature04108] [PMID: 16251967]
[http://dx.doi.org/10.1074/jbc.M109.069450] [PMID: 20064927]
[http://dx.doi.org/10.1158/0008-5472.CAN-09-2668] [PMID: 20028861]
[http://dx.doi.org/10.1016/j.cell.2006.10.018] [PMID: 17081971]
[http://dx.doi.org/10.1038/nri1529] [PMID: 15630426]
[http://dx.doi.org/10.1254/jphs.CR0070024] [PMID: 17721040]
[http://dx.doi.org/10.1038/srep38331] [PMID: 27910912]
[http://dx.doi.org/10.1038/s41598-017-09655-7] [PMID: 28831201]
[http://dx.doi.org/10.1111/cpr.12433] [PMID: 29341317]
[http://dx.doi.org/10.1186/1476-4598-12-116] [PMID: 24098916]
[http://dx.doi.org/10.1002/ardp.201000069] [PMID: 21290430]
[http://dx.doi.org/10.1007/s11164-018-3319-y]