Abstract
An important bioactive heterocycle having several uses in medicinal chemistry, synthetic organic chemistry, material chemistry, and natural product is indole along with its analogues. Many bioactive indole-based heterocycles have important antibacterial, anti-inflammatory, analgesic, antiviral, antimalarial, chemotherapeutic, antifungal, and anti-TB effects, as well as antioxidant capabilities. Several well-known medications, including tadalafil, rizatriptan, sumatriptan, and fluvastatin are indole- based potential bioactive compounds. Based on the existing and latest evidence, researchers have focused on developing indole-based compounds with novel biological and pharmacological properties for decades. Owing to useful bioactivities, we have described many bioactive indoles and their synthetic methods in this review article.
Graphical Abstract
[http://dx.doi.org/10.1016/j.cclet.2016.12.037]
[http://dx.doi.org/10.1021/acs.jmedchem.5b01219] [PMID: 26757340]
[http://dx.doi.org/10.1080/14786419.2016.1277351] [PMID: 28067066]
[http://dx.doi.org/10.1016/j.bmc.2005.05.053] [PMID: 16002298]
[http://dx.doi.org/10.1016/j.antiviral.2009.05.001] [PMID: 19445965]
[http://dx.doi.org/10.1002/ardp.202000131] [PMID: 32785974]
[http://dx.doi.org/10.1021/np50018a014] [PMID: 7334384]
[http://dx.doi.org/10.1021/jf60200a041] [PMID: 1170225]
[http://dx.doi.org/10.1016/j.bmcl.2016.02.043] [PMID: 26920799]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.059] [PMID: 20727623]
[http://dx.doi.org/10.1021/jm00120a002] [PMID: 2848124]
[http://dx.doi.org/10.1021/cr60095a004]
[http://dx.doi.org/10.1021/cr020033s] [PMID: 12630855]
[http://dx.doi.org/10.1002/ejoc.200800397]
[http://dx.doi.org/10.1016/S0960-894X(99)00133-X] [PMID: 10230641]
[http://dx.doi.org/10.1021/jm501100b] [PMID: 25255204]
[http://dx.doi.org/10.1016/j.jchromb.2003.09.029] [PMID: 15036011]
[http://dx.doi.org/10.1016/j.ejmech.2011.01.062] [PMID: 21353349]
[http://dx.doi.org/10.1016/0010-938X(83)90081-1]
[http://dx.doi.org/10.1016/j.matlet.2007.04.079]
[http://dx.doi.org/10.1021/ja907380d] [PMID: 19950948]
[http://dx.doi.org/10.1002/pol.1984.170220220]
[http://dx.doi.org/10.1002/chem.200802140] [PMID: 19132705]
[http://dx.doi.org/10.1002/asia.201000310] [PMID: 20922748]
[http://dx.doi.org/10.1002/jhet.5570370322]
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
[http://dx.doi.org/10.1055/s-2003-40507]
[http://dx.doi.org/10.1002/anie.200600588] [PMID: 16637095]
[http://dx.doi.org/10.1039/C5NP00032G] [PMID: 26151910]
[http://dx.doi.org/10.1021/ja036191y] [PMID: 14611249]
[http://dx.doi.org/10.1016/j.bmcl.2004.01.071] [PMID: 15050637]
[http://dx.doi.org/10.1016/j.bioorg.2019.103021] [PMID: 31176854]
[http://dx.doi.org/10.1021/cc9900192] [PMID: 10748736]
[http://dx.doi.org/10.1021/cc000002f] [PMID: 10827923]
[http://dx.doi.org/10.1021/cc010049g] [PMID: 11703143]
[http://dx.doi.org/10.1016/S0040-4020(97)00476-6]
[http://dx.doi.org/10.1021/cr050521a] [PMID: 16351058]
[http://dx.doi.org/10.3390/molecules20022973] [PMID: 25685907]
[http://dx.doi.org/10.1016/j.lfs.2005.09.007] [PMID: 16236327]
[http://dx.doi.org/10.2174/092986712803341449] [PMID: 22830349]
[http://dx.doi.org/10.1080/15438620600987106] [PMID: 17214405]
[http://dx.doi.org/10.1126/science.1176827] [PMID: 19965390]
[http://dx.doi.org/10.1136/ebmh.7.4.107] [PMID: 15504795]
[http://dx.doi.org/10.1517/13543784.17.7.1085] [PMID: 18549344]
[http://dx.doi.org/10.1016/j.antiviral.2008.10.009] [PMID: 19028526]
[http://dx.doi.org/10.1126/scitranslmed.3004404] [PMID: 23253612]
[http://dx.doi.org/10.1086/605630] [PMID: 19739972]
[http://dx.doi.org/10.1016/j.bmcl.2010.01.159] [PMID: 20176480]
[http://dx.doi.org/10.1093/cid/ciq146] [PMID: 21208910]
[http://dx.doi.org/10.1016/j.ijmm.2016.05.010] [PMID: 27259840]
[http://dx.doi.org/10.1021/cen-v068n020.p042]
[http://dx.doi.org/10.1146/annurev.med.60.042307.110802] [PMID: 19630576]
[http://dx.doi.org/10.2174/092986707781058805] [PMID: 17627520]
[http://dx.doi.org/10.4274/tjps.55707] [PMID: 32454672]
[http://dx.doi.org/10.1007/s11164-016-2696-3]
[http://dx.doi.org/10.1039/c3cs60386e] [PMID: 24492745]
[http://dx.doi.org/10.1016/j.ejmech.2014.11.033] [PMID: 25563511]
[PMID: 26330857]
[http://dx.doi.org/10.1016/j.bmc.2007.03.024] [PMID: 17395469]
b) Brooks, C.D.W.; Craig, R.A.; Gunn, D.E.; Kolasa, T.; Moore, J.L.; Stewart, A.O.; Int, P.C.T.WO. Pat. 9741100 1998.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.056] [PMID: 25462246]
[http://dx.doi.org/10.1023/B:NERE.0000042208.20730.23] [PMID: 15532537]
[http://dx.doi.org/10.1016/j.jneuroim.2005.05.002] [PMID: 15975667]
[http://dx.doi.org/10.1016/j.ejmech.2007.10.012] [PMID: 18063224]
[http://dx.doi.org/10.2478/v10007-008-0028-x] [PMID: 19103580];
b) Winter, C.A.; Risley, E.A.; Nuss, G.W. Exp. Biol. Med. (Maywood), 1962, 111(3), 544-547.
[http://dx.doi.org/10.3181/00379727-111-27849] [PMID: 14001233]
[http://dx.doi.org/10.1016/j.ejmech.2014.03.003] [PMID: 24631898];
b) Sakurada, T.; Matsumura, T.; Moriyama, T.; Sakurada, C.; Ueno, S.; Sakurada, S. Pharmacology Biochemistry and Behavior, 2003, 75, 115-121.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.025] [PMID: 20621732]
[http://dx.doi.org/10.1016/j.bmcl.2011.04.001] [PMID: 21524574]
[http://dx.doi.org/10.1002/chem.201303510] [PMID: 24243627]
[http://dx.doi.org/10.1124/jpet.107.126680] [PMID: 17660383]
[http://dx.doi.org/10.1021/ja103472a] [PMID: 20486685]
[http://dx.doi.org/10.1016/j.ejmech.2014.10.065] [PMID: 25462257]
[http://dx.doi.org/10.1016/j.antiviral.2014.07.014] [PMID: 25108173]
[http://dx.doi.org/10.1177/095632020601700504] [PMID: 17176631]
[http://dx.doi.org/10.1016/j.apsb.2014.06.003] [PMID: 26579401]
[http://dx.doi.org/10.1016/j.bmc.2003.10.013] [PMID: 14697775]
[http://dx.doi.org/10.1016/j.ejmech.2019.02.019] [PMID: 30798050]
[http://dx.doi.org/10.1016/j.febslet.2011.04.042] [PMID: 21530510]
[http://dx.doi.org/10.1016/j.trstmh.2007.10.002] [PMID: 18035385]
[http://dx.doi.org/10.1016/j.bmc.2005.02.017] [PMID: 15781403]
[http://dx.doi.org/10.1021/ol802506n] [PMID: 19090698]
[http://dx.doi.org/10.1021/jm950395a] [PMID: 8576907]
[http://dx.doi.org/10.1161/01.CIR.0000103683.99399.7E] [PMID: 14662691]
[http://dx.doi.org/10.1021/jm980264k] [PMID: 9685232]
[http://dx.doi.org/10.1016/j.phrs.2007.08.002] [PMID: 17889553]
[http://dx.doi.org/10.1016/j.bmcl.2009.12.107] [PMID: 20079636]
[http://dx.doi.org/10.1126/science.1073126] [PMID: 12130767]
[http://dx.doi.org/10.2174/157018008784619915]
[http://dx.doi.org/10.1080/10611860410001712696] [PMID: 15203896]
[http://dx.doi.org/10.1016/j.bbrc.2005.10.121] [PMID: 16288723]
[http://dx.doi.org/10.1016/j.bmcl.2007.04.035] [PMID: 17548194]
[http://dx.doi.org/10.1016/j.bmcl.2013.11.018] [PMID: 24314395]
[http://dx.doi.org/10.1126/science.1185449] [PMID: 20466923]
[http://dx.doi.org/10.1016/j.jtusci.2016.09.002]
[http://dx.doi.org/10.1016/j.bmcl.2009.04.029] [PMID: 19403307]
[http://dx.doi.org/10.1111/cbdd.12230] [PMID: 24103309]
[http://dx.doi.org/10.1248/cpb.c12-00651] [PMID: 23183543]
[http://dx.doi.org/10.1002/jps.2600720330] [PMID: 6842387]
[http://dx.doi.org/10.1002/ardp.202000100] [PMID: 32909304]
[http://dx.doi.org/10.1002/ardp.200700161] [PMID: 18404776]
[http://dx.doi.org/10.1016/j.bmc.2008.12.058] [PMID: 19157884]
[http://dx.doi.org/10.1016/j.ejmech.2014.04.043] [PMID: 24813879]
[http://dx.doi.org/10.1016/j.bmc.2008.02.091] [PMID: 18378462]
[http://dx.doi.org/10.1007/BF02976488] [PMID: 11235807]
[http://dx.doi.org/10.1021/jm0307741] [PMID: 12825930]
[http://dx.doi.org/10.1016/j.bmcl.2006.09.034] [PMID: 17027264]
[http://dx.doi.org/10.1016/j.bmc.2014.02.008] [PMID: 24613628]
[http://dx.doi.org/10.1002/bio.748] [PMID: 14981640]
[http://dx.doi.org/10.1016/j.bmc.2009.07.077] [PMID: 19683932]
[http://dx.doi.org/10.1248/cpb.50.165] [PMID: 11848203]
[PMID: 15378805]
[http://dx.doi.org/10.1021/jm101614j] [PMID: 21366296]
[http://dx.doi.org/10.1021/jm300477h] [PMID: 22712652]
[http://dx.doi.org/10.1021/jm101142k] [PMID: 21142105]
[http://dx.doi.org/10.1016/j.bmcl.2009.07.076] [PMID: 19664921]
[http://dx.doi.org/10.1007/978-1-4615-4913-0]
[http://dx.doi.org/10.1007/s10295-013-1366-3] [PMID: 24146366]
[http://dx.doi.org/10.1007/s10295-013-1386-z] [PMID: 24342965]
[http://dx.doi.org/10.1016/j.bmcl.2005.08.059] [PMID: 16183286]
[http://dx.doi.org/10.5012/bkcs.2010.31.11.3467]
[http://dx.doi.org/10.1021/jo00289a036]
[http://dx.doi.org/10.1016/j.bmcl.2006.09.076] [PMID: 17046257]
[http://dx.doi.org/10.1016/j.ejmech.2003.11.002] [PMID: 15110970]
[http://dx.doi.org/10.1016/j.bmcl.2009.07.091] [PMID: 19660944]
[http://dx.doi.org/10.1002/jhet.3021]
[http://dx.doi.org/10.1111/cbdd.12613] [PMID: 26132412]
[http://dx.doi.org/10.1007/s11094-013-0973-7]
[http://dx.doi.org/10.1016/S0040-4039(01)01492-7]
[http://dx.doi.org/10.1016/j.tetlet.2013.12.081] [PMID: 24678129]
[http://dx.doi.org/10.1007/s10593-014-1395-5]
[http://dx.doi.org/10.1039/C4RA11428K]
[http://dx.doi.org/10.1007/s11164-016-2478-y]