Abstract
The oxadiazole core is considered a privileged moiety in many medicinal chemistry applications. The oxadiazole class includes 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,5-oxadiazole. Compounds bearing an oxadiazole ring show a wide range of biological activities, such as anticancer, antibacterial, anti-inflammatory, anti-malarial, and insecticidal properties. Among oxadiazoles, the 1,3,4-oxadiazole has been the most widely explored moiety in medicinal chemistry research. This review is primarily focused on the anticancer, antibacterial, and anti-inflammatory activities of compounds containing 1,2,4-oxadiazole, 1,3,4-oxadiazole and 1,2,5-oxadiazole reported in the last five years.
Keywords: Heterocyclic compounds, Oxadiazole, Anticancer, Antibacterial, Anti-inflammatory, SAR.
Graphical Abstract
[http://dx.doi.org/10.3390/molecules23123361] [PMID: 30567416]
[http://dx.doi.org/10.1007/BFb0051520]
[http://dx.doi.org/10.1080/00397911.2017.1360911]
[http://dx.doi.org/10.1021/jm2013248] [PMID: 22185670]
[http://dx.doi.org/10.1016/j.arabjc.2014.09.003]
[http://dx.doi.org/10.1016/j.ejmech.2017.12.044] [PMID: 29288945]
[http://dx.doi.org/10.5530/ijper.53.2s.44]
[http://dx.doi.org/10.2174/138955711797655407] [PMID: 22353222]
[http://dx.doi.org/10.1016/j.ejmech.2015.04.051] [PMID: 25965776]
[http://dx.doi.org/10.1016/j.ejmech.2016.09.023] [PMID: 27662031]
[http://dx.doi.org/10.2174/1389557518666181015152433] [PMID: 30324877]
[http://dx.doi.org/10.1016/j.bfopcu.2014.10.001]
[http://dx.doi.org/10.1016/j.jsps.2016.07.004] [PMID: 28344487]
[http://dx.doi.org/10.1016/j.bfopcu.2017.06.001]
[http://dx.doi.org/10.1016/j.jscs.2011.12.017]
[http://dx.doi.org/10.1016/j.jscs.2012.04.010]
[http://dx.doi.org/10.3390/molecules170910192] [PMID: 22926303]
[http://dx.doi.org/10.2174/138955712801264800] [PMID: 22512560]
[http://dx.doi.org/10.2174/092986711793979733] [PMID: 21110816]
[http://dx.doi.org/10.1080/15257770.2019.1615623] [PMID: 31135268]
[http://dx.doi.org/10.1007/s12272-019-01114-3] [PMID: 30661200]
[http://dx.doi.org/10.1016/j.biopha.2019.108612] [PMID: 30798142]
[http://dx.doi.org/10.7150/ijms.3635] [PMID: 22408567]
[http://dx.doi.org/10.1148/radiol.09082134] [PMID: 20032159]
[http://dx.doi.org/10.1111/j.1442-2042.1997.tb00282.x] [PMID: 9354943]
[http://dx.doi.org/10.1016/j.ejmech.2019.03.025] [PMID: 30953881]
[http://dx.doi.org/10.5306/wjco.v7.i1.54] [PMID: 26862491]
[http://dx.doi.org/10.1073/pnas.92.12.5258] [PMID: 7777494]
[http://dx.doi.org/10.3322/canjclin.19.4.202] [PMID: 4979758]
[http://dx.doi.org/10.2174/1568026619666190618130008] [PMID: 31210108]
[http://dx.doi.org/10.1016/j.bmcl.2017.07.015] [PMID: 28716494]
[http://dx.doi.org/10.2174/1568026619666190603094439] [PMID: 31161992]
[http://dx.doi.org/10.1016/j.ejmech.2015.04.002] [PMID: 25874326]
[http://dx.doi.org/10.1016/j.bmc.2015.04.028] [PMID: 25953722]
[http://dx.doi.org/10.1016/j.bmc.2016.09.022] [PMID: 27665180]
[http://dx.doi.org/10.1016/j.ejmech.2018.12.049] [PMID: 30594030]
[http://dx.doi.org/10.1016/j.bmc.2015.05.060] [PMID: 26169762]
[http://dx.doi.org/10.2174/1570180815666180219165119]
[http://dx.doi.org/10.2174/1871520615666150907093855] [PMID: 26343141]
[http://dx.doi.org/10.1016/j.bioorg.2016.02.007] [PMID: 26943479]
[http://dx.doi.org/10.1021/acs.jmedchem.6b00468] [PMID: 27801583]
[http://dx.doi.org/10.1016/j.ejmech.2017.03.017] [PMID: 28324784]
[http://dx.doi.org/10.1016/j.bmcl.2014.12.067] [PMID: 25599837]
[http://dx.doi.org/10.1016/j.bioorg.2018.02.020] [PMID: 29533215]
[http://dx.doi.org/10.1016/j.bioorg.2018.05.011] [PMID: 29803079]
[http://dx.doi.org/10.1016/j.compbiolchem.2018.05.013] [PMID: 30015176]
[http://dx.doi.org/10.1016/j.bmc.2017.03.038] [PMID: 28363444]
[http://dx.doi.org/10.1016/j.ejmech.2018.06.049] [PMID: 29966916]
[http://dx.doi.org/10.1016/j.bmcl.2018.02.008] [PMID: 29456106]
[http://dx.doi.org/10.1016/j.bioorg.2016.09.002] [PMID: 27656775]
[http://dx.doi.org/10.1016/j.ejmech.2016.12.014] [PMID: 27987485]
[http://dx.doi.org/10.1016/j.ejmech.2019.02.033] [PMID: 30798049]
[http://dx.doi.org/10.1111/cbdd.12936] [PMID: 28067996]
[http://dx.doi.org/10.1007/s00280-017-3414-6] [PMID: 28815320]
[http://dx.doi.org/10.3390/molecules22071109] [PMID: 28677624]
[http://dx.doi.org/10.1016/j.tetlet.2018.09.011]
[http://dx.doi.org/10.1016/j.jinorgbio.2015.11.020] [PMID: 26684582]
[http://dx.doi.org/10.1016/j.bmcl.2015.03.001] [PMID: 25801936]
[http://dx.doi.org/10.1016/j.bmcl.2016.04.058] [PMID: 27156770]
[http://dx.doi.org/10.1016/j.bioorg.2018.01.007] [PMID: 29353728]
[http://dx.doi.org/10.1016/j.ejmech.2014.11.011] [PMID: 25461310]
[http://dx.doi.org/10.1016/j.bmcl.2016.08.014] [PMID: 27542307]
[http://dx.doi.org/10.1016/j.ejmech.2017.03.084] [PMID: 28410493]
[http://dx.doi.org/10.1016/j.ejmech.2019.01.001] [PMID: 30654237]
[http://dx.doi.org/10.1016/j.heliyon.2019.e01255] [PMID: 30886919]
[http://dx.doi.org/10.1016/j.ejmech.2016.02.015] [PMID: 26900655]
[http://dx.doi.org/10.1016/j.ejmech.2016.10.052] [PMID: 27823888]
[http://dx.doi.org/10.1080/15257770.2017.1327665] [PMID: 28613111]
[http://dx.doi.org/10.1093/cid/cix881] [PMID: 29040428]
[http://dx.doi.org/10.3390/ijms16023626] [PMID: 25667977]
[http://dx.doi.org/10.1002/chem.201202948] [PMID: 23296491]
[http://dx.doi.org/10.1016/j.cmi.2016.01.011] [PMID: 26812445]
[http://dx.doi.org/10.1016/j.bmc.2004.07.029] [PMID: 15388173]
[http://dx.doi.org/10.2147/IDR.S55778] [PMID: 25878509]
[http://dx.doi.org/10.1021/jm960294s] [PMID: 8831751]
[http://dx.doi.org/10.1128/JCM.00154-08] [PMID: 18508934]
[http://dx.doi.org/10.1016/j.tifs.2016.03.010]
[http://dx.doi.org/10.1039/C7CS00748E] [PMID: 30462112]
[http://dx.doi.org/10.1016/j.bmcl.2015.12.041] [PMID: 26733473]
[http://dx.doi.org/10.1016/j.bmcl.2016.09.059] [PMID: 27727124]
[http://dx.doi.org/10.1016/j.arabjc.2011.11.009]
[http://dx.doi.org/10.4314/tjpr.v14i11.14]
[http://dx.doi.org/10.4155/fmc-2017-0159] [PMID: 29334249]
[http://dx.doi.org/10.1016/j.ejmech.2017.02.046] [PMID: 28246042]
[http://dx.doi.org/10.1016/j.bmc.2016.03.011] [PMID: 26972920]
[http://dx.doi.org/10.1007/s10534-017-0046-6] [PMID: 28840394]
[http://dx.doi.org/10.1080/14756366.2017.1396456] [PMID: 29148294]
[http://dx.doi.org/10.1016/j.bmcl.2015.11.057] [PMID: 26675440]
[http://dx.doi.org/10.1016/j.ejmech.2016.07.039] [PMID: 27508879]
[http://dx.doi.org/10.1016/j.ejmech.2018.04.017] [PMID: 29679902]
[http://dx.doi.org/10.1007/s00044-017-2098-0]
[http://dx.doi.org/10.1016/j.bmcl.2016.02.043] [PMID: 26920799]
[http://dx.doi.org/10.1016/j.bmc.2017.08.010] [PMID: 28835350]
[http://dx.doi.org/10.1111/cbdd.12969] [PMID: 28267891]
[http://dx.doi.org/10.1016/j.bmc.2017.08.015] [PMID: 29032931]
[http://dx.doi.org/10.1016/j.pestbp.2017.10.011] [PMID: 29933979]
[http://dx.doi.org/10.1021/acs.jafc.7b06061] [PMID: 29502398]
[http://dx.doi.org/10.1016/j.ijantimicag.2017.04.016] [PMID: 28687457]
[http://dx.doi.org/10.4314/tjpr.v15i6.20]
[http://dx.doi.org/10.1002/jhet.3409]
[http://dx.doi.org/10.1016/j.ejmech.2016.12.016] [PMID: 27988464]
[http://dx.doi.org/10.1007/s00044-016-1511-4]
[http://dx.doi.org/10.1007/s11164-016-2736-z]
[http://dx.doi.org/10.1007/s11030-015-9640-0] [PMID: 26498121]
[http://dx.doi.org/10.1074/jbc.M603819200] [PMID: 16956889]
[http://dx.doi.org/10.1016/j.molimm.2005.03.015] [PMID: 15869794]
[http://dx.doi.org/10.4049/jimmunol.179.11.7344] [PMID: 18025177]
[http://dx.doi.org/10.1155/2013/210736] [PMID: 23840248]
[http://dx.doi.org/10.1038/bjp.2008.136] [PMID: 18454171]
[http://dx.doi.org/10.1038/sj.bjp.0705231] [PMID: 12746218]
[http://dx.doi.org/10.1016/j.niox.2012.10.003] [PMID: 23085209]
[http://dx.doi.org/10.4049/jimmunol.1002993] [PMID: 21876038]
[http://dx.doi.org/10.1016/j.fitote.2017.10.015] [PMID: 29066299]
[http://dx.doi.org/10.1016/j.molstruc.2018.01.060]
[http://dx.doi.org/10.1016/j.bmcl.2018.04.021] [PMID: 29678461]
[http://dx.doi.org/10.1016/j.bioorg.2016.09.005] [PMID: 27669120]
[http://dx.doi.org/10.1016/j.bioorg.2016.10.003] [PMID: 27750057]
[http://dx.doi.org/10.1016/j.bioorg.2016.11.014] [PMID: 27923497]
[http://dx.doi.org/10.1016/j.bioorg.2017.06.003] [PMID: 28738249]
[http://dx.doi.org/10.1016/j.ejmech.2015.06.020] [PMID: 26117820]
[http://dx.doi.org/10.1016/j.biopha.2018.04.167] [PMID: 29864929]
[http://dx.doi.org/10.1016/j.bioorg.2017.01.015] [PMID: 28160943]
[http://dx.doi.org/10.2174/1573406414666180321141555] [PMID: 29564980]
[http://dx.doi.org/10.1007/s11010-016-2888-6] [PMID: 27928710]
[http://dx.doi.org/10.1016/j.ejmech.2015.12.046] [PMID: 26774922]
[http://dx.doi.org/10.1016/j.bmc.2016.09.013] [PMID: 27667552]
[http://dx.doi.org/10.1016/j.bmcl.2016.12.083] [PMID: 28108247]
[http://dx.doi.org/10.1016/j.bmcl.2015.02.069] [PMID: 25900217]
[http://dx.doi.org/10.1080/10426507.2017.1394302]
[http://dx.doi.org/10.1016/j.bmcl.2016.08.059] [PMID: 27575481]
[http://dx.doi.org/10.1016/j.bmc.2015.06.053] [PMID: 26164624]
[http://dx.doi.org/10.1016/j.ejmech.2017.12.020] [PMID: 29274492]
[http://dx.doi.org/10.1021/acs.jafc.8b02124] [PMID: 30134651]
[http://dx.doi.org/10.1021/acs.jafc.8b03020] [PMID: 30145894]
[http://dx.doi.org/10.1007/s11030-018-9823-6] [PMID: 29572759]
[http://dx.doi.org/10.1007/s12272-014-0378-5] [PMID: 24838380]
[http://dx.doi.org/10.3390/molecules22111811] [PMID: 29109386]
[http://dx.doi.org/10.1002/ps.5229] [PMID: 30284404]
[http://dx.doi.org/10.1038/srep31045] [PMID: 27530962]
[http://dx.doi.org/10.1007/s11030-018-9837-0] [PMID: 29808346]