Abstract
Among the large variety of nitrogen and oxygen-containing heterocycles, 1,3,4- oxadiazole, the scaffold, has attracted considerable attention owing to its ability to show an extensive range of pharmacological actions. According to literature investigations, prepared 1,3,4- oxadiazole and its derivative are pharmacologically significant and consist of a variety of activities, such as anticonvulsant, anticancer, antioxidant, anti-inflammatory, antibacterial, antidiabetic, etc. These heterocyclics are formed mainly by the cyclization reactions of various reactants under diverse reaction circumstances. Therefore, significant efforts of organic chemists have been directed towards the synthesis of new drug candidates containing 1,3,4-oxadiazole subunits connected to an established potential pharmacophore to improve the efficacy and potency. This article aims to highlight recent publications on the various synthesis techniques of 1,3,4-oxadiazole and related compounds over the previous ten years (2011–2021). The purpose of this review is to help researchers by summarizing several synthetic strategies for synthesizing oxadiazole.
Keywords: Heterocycles, 1, 3, 4-oxadiazole, pharmacological actions, synthetic strategies, isomers, biological potential.
Graphical Abstract
[http://dx.doi.org/10.3390/molecules16064339] [PMID: 21613975]
[http://dx.doi.org/10.3184/030823401103169603]
[http://dx.doi.org/10.1021/jm2013248] [PMID: 22185670]
[http://dx.doi.org/10.1074/jbc.272.18.12151] [PMID: 9115286]
[http://dx.doi.org/10.1186/2191-2858-2-8] [PMID: 22380426]
[http://dx.doi.org/10.1016/j.bmcl.2007.04.004] [PMID: 17467984]
[http://dx.doi.org/10.1002/jccs.200700002]
[http://dx.doi.org/10.1016/j.ejmech.2008.01.039] [PMID: 18395299]
[http://dx.doi.org/10.1080/00397911.2017.1360911]
[http://dx.doi.org/10.2174/138955712801264800] [PMID: 22512560]
[http://dx.doi.org/10.1021/ja055438j] [PMID: 16332087]
[http://dx.doi.org/10.1016/S0065-2725(08)60151-8]
[http://dx.doi.org/10.1016/j.bmcl.2009.01.089] [PMID: 19217284]
[http://dx.doi.org/10.1021/jm0342414] [PMID: 15027850]
[http://dx.doi.org/10.1021/jm901268n] [PMID: 19894742]
[http://dx.doi.org/10.1016/j.ejmech.2009.12.072] [PMID: 20110137]
[http://dx.doi.org/10.1248/cpb.56.509] [PMID: 18379099]
[http://dx.doi.org/10.1016/j.bmcl.2005.02.014] [PMID: 15780622]
[http://dx.doi.org/10.1016/j.ejmech.2009.04.006] [PMID: 19423197]
[http://dx.doi.org/10.1016/j.bmc.2010.04.021] [PMID: 20452224]
[http://dx.doi.org/10.1016/j.cbi.2009.07.014] [PMID: 19643099]
[http://dx.doi.org/10.1016/j.ejmech.2012.04.015] [PMID: 22575535]
[http://dx.doi.org/10.1021/jm201504s] [PMID: 22429006]
[http://dx.doi.org/10.1002/1099-0690(200010)2000:20<3363:AID-EJOC3363>3.0.CO;2-I]
[http://dx.doi.org/10.1517/13543784.15.12.1507] [PMID: 17107277]
[http://dx.doi.org/10.1021/ml100029k] [PMID: 24900191]
[http://dx.doi.org/10.1021/jm00232a010] [PMID: 994153]
[http://dx.doi.org/10.1016/j.bmcl.2005.11.094] [PMID: 16377187]
[http://dx.doi.org/10.1080/00397911.2013.879901]
[http://dx.doi.org/10.7164/antibiotics.24.443] [PMID: 4327309]
[http://dx.doi.org/10.1016/j.tetlet.2011.05.146]
[http://dx.doi.org/10.1021/jo2025509] [PMID: 22423599]
[http://dx.doi.org/10.1016/j.tetlet.2004.02.119]
[http://dx.doi.org/10.1016/j.tet.2012.11.071]
[http://dx.doi.org/10.1021/jo0618730] [PMID: 17137395]
[http://dx.doi.org/10.1021/jo302324r] [PMID: 23215154]
[http://dx.doi.org/10.1016/j.tetlet.2008.09.057]
[http://dx.doi.org/10.1016/j.tet.2011.05.100]
[http://dx.doi.org/10.1002/ardp.200700146] [PMID: 18293435]
[http://dx.doi.org/10.1016/j.tetlet.2006.05.033]
[http://dx.doi.org/10.1016/j.tetlet.2009.02.054]
[http://dx.doi.org/10.1080/00397910903134592]
[http://dx.doi.org/10.1515/hc-2012-0179]
[http://dx.doi.org/10.1016/j.ejmech.2010.06.023] [PMID: 20630627]
[http://dx.doi.org/10.1016/j.bmcl.2011.04.142] [PMID: 21612921]
[http://dx.doi.org/10.1021/ol202409r] [PMID: 22007797]
[http://dx.doi.org/10.1021/jf303807a] [PMID: 23134289]
[http://dx.doi.org/10.1021/jo400023z] [PMID: 23394598]
[http://dx.doi.org/10.1016/j.tetlet.2006.07.127]
[http://dx.doi.org/10.1080/00397910802054289]
[http://dx.doi.org/10.1016/j.bmcl.2013.01.041] [PMID: 23434418]
[http://dx.doi.org/10.1055/s-0033-1341043]
[http://dx.doi.org/10.1134/S1023193510010040]
[http://dx.doi.org/10.1016/j.cclet.2013.05.032]
[http://dx.doi.org/10.1016/j.tetlet.2010.06.139]
[http://dx.doi.org/10.1016/j.tetlet.2018.01.037]
[http://dx.doi.org/10.1039/C1OB06512B] [PMID: 22159592]
[http://dx.doi.org/10.1590/S0103-50532008000800024]
[http://dx.doi.org/10.1016/j.ejmech.2013.02.040] [PMID: 23535322]
[http://dx.doi.org/10.1081/SCC-120039492]
[http://dx.doi.org/10.1021/ol200326u] [PMID: 21381681]
[http://dx.doi.org/10.1021/ol100931q] [PMID: 20481612]
[http://dx.doi.org/10.1016/j.tetlet.2006.05.051]
[http://dx.doi.org/10.1016/j.tetlet.2006.07.032]
[http://dx.doi.org/10.1016/j.tetlet.2011.10.152]
[http://dx.doi.org/10.1016/j.tetlet.2007.11.165]
[http://dx.doi.org/10.1016/j.ejmech.2013.04.054] [PMID: 23727537]
[http://dx.doi.org/10.14233/ajchem.2019.22061]
[http://dx.doi.org/10.1002/anie.202107536]
[http://dx.doi.org/10.1021/cr0306790] [PMID: 15137807]
[http://dx.doi.org/10.1016/j.ejmech.2017.03.039] [PMID: 28364658]
[http://dx.doi.org/10.5530/ijper.51.2.31]
[http://dx.doi.org/10.1016/j.ejmech.2016.10.052] [PMID: 27823888]
[http://dx.doi.org/10.1016/j.bmc.2013.11.004] [PMID: 24286761]
[http://dx.doi.org/10.1021/jm500303u] [PMID: 24972008]
[http://dx.doi.org/10.1016/j.arabjc.2015.08.019]
[http://dx.doi.org/10.1016/j.molstruc.2015.07.067]
[http://dx.doi.org/10.1016/j.bmcl.2016.04.058] [PMID: 27156770]
[http://dx.doi.org/10.1016/j.ejmech.2015.12.026] [PMID: 26717204]
[http://dx.doi.org/10.1155/2011/240196]
[http://dx.doi.org/10.3797/scipharm.0912-16] [PMID: 21179342]
[http://dx.doi.org/10.1007/s12039-010-0019-6]
[PMID: 20524426]
[http://dx.doi.org/10.3390/molecules14051898] [PMID: 19471209]
[http://dx.doi.org/10.1016/S0014-827X(98)00063-9] [PMID: 10081816]
[PMID: 24250678]
[http://dx.doi.org/10.1016/j.bmcl.2010.05.059] [PMID: 20558061]
[http://dx.doi.org/10.1016/j.ejmech.2010.02.060] [PMID: 20392546]
[http://dx.doi.org/10.1007/s00044-010-9496-x]
[http://dx.doi.org/10.3923/ijp.2010.696.704]
[http://dx.doi.org/10.1111/j.1747-0285.2010.01066.x] [PMID: 21266018]
[http://dx.doi.org/10.1016/j.bioorg.2017.12.037] [PMID: 29316509]