Abstract
Thiocoumarins and dithiocoumarins are two important classes of sulphurcontaining heterocyclic compounds, which are bioisosteres of coumarins. Herein, various synthetic strategies for these two classes of heterocyclic compounds reported in the literature have been discussed. Different solvents, catalysts, reagents and reaction conditions, which were employed successfully for synthesizing thiocoumarins and dithiocoumarins have also been described concisely in this review. Mechanistic overview has been given wherever it was necessary. In addition, a comparative view of various solvents, catalysts and reagents focusing on their efficiency for synthesizing thiocoumarins and dithiocoumarins, has been discussed as well. Furthermore, pharmacological activities of these two classes of compounds have also been discussed.
Keywords: Advances, bioisosteres, dithiocoumarins, heterocycles, pharmacological activity, synthesis, thiocoumarins, thiooxocoumarins.
Graphical Abstract
[http://dx.doi.org/10.1002/andp.18200640205]
[http://dx.doi.org/10.1016/j.saa.2006.08.023] [PMID: 17023196]
[http://dx.doi.org/10.1002/jps.2600530302] [PMID: 14191429]
[http://dx.doi.org/10.1039/np9890600591] [PMID: 2699016]
[http://dx.doi.org/10.1039/np9971400465] [PMID: 9364778]
[http://dx.doi.org/10.2174/1389557516666160801094919] [PMID: 27488585]
[http://dx.doi.org/10.2174/092986711803414395] [PMID: 21824098]
[http://dx.doi.org/10.2174/0929867325666180104154443] [PMID: 29303071]
[http://dx.doi.org/10.1371/journal.pone.0164585]
[http://dx.doi.org/10.1039/C4NP00162A] [PMID: 26151411]
[http://dx.doi.org/10.1155/2013/963248] [PMID: 23586066]
[http://dx.doi.org/10.1080/14756360409162453] [PMID: 15558956]
[http://dx.doi.org/10.1021/jm901287j] [PMID: 19911821]
[http://dx.doi.org/10.2174/1568011053352550] [PMID: 15720259]
[http://dx.doi.org/10.2174/092986710790936284] [PMID: 20166938]
[http://dx.doi.org/10.2174/1570180812666150901222106]
[http://dx.doi.org/10.3389/fchem.2019.00366] [PMID: 31179271]
[http://dx.doi.org/10.1021/jm101104z] [PMID: 21138273]
[http://dx.doi.org/10.2174/0929867053507315] [PMID: 15853704]
[PMID: 5720680]
[http://dx.doi.org/10.1038/181571a0] [PMID: 13517225]
[http://dx.doi.org/10.1016/0006-2952(74)90351-7] [PMID: 4441426]
[http://dx.doi.org/10.1002/j.1537-2197.1950.tb12186.x]
[http://dx.doi.org/10.1016/S0065-2725(08)60140-3]
[http://dx.doi.org/10.1021/cr60113a001]
[http://dx.doi.org/10.1007/BF00899270]
[http://dx.doi.org/10.1007/BF00905722]
[http://dx.doi.org/10.1002/ardp.19673000615] [PMID: 5249955]
[http://dx.doi.org/10.1002/bscb.19700791107]
[http://dx.doi.org/10.1055/s-1975-23918]
[http://dx.doi.org/10.1055/s-1984-30890]
[http://dx.doi.org/10.1021/ja01278a055]
[http://dx.doi.org/10.5012/bkcs.2007.28.7.1203]
[http://dx.doi.org/10.1021/jo00987a028]
[http://dx.doi.org/10.1016/j.arabjc.2012.04.027]
[http://dx.doi.org/10.15227/orgsyn.012.0076]
[http://dx.doi.org/10.1002/cber.19120450288]
[http://dx.doi.org/10.1039/dt9830000143]
[http://dx.doi.org/10.1039/JR9620000740]
[http://dx.doi.org/10.1071/CH9761413]
[http://dx.doi.org/10.1055/s-1989-28357]
[http://dx.doi.org/10.1055/s-1988-27501]
[http://dx.doi.org/10.1016/S0040-4039(00)75204-X]
[http://dx.doi.org/10.1021/jo01258a106]
[http://dx.doi.org/10.1039/p19720000817]
[http://dx.doi.org/10.1515/znb-1968-0305]
[http://dx.doi.org/10.1002/bscb.19700790109]
[http://dx.doi.org/10.1002/bscb.19690780914]
[http://dx.doi.org/10.1002/bscb.19660750304]
[http://dx.doi.org/10.1002/cber.19600930115]
[http://dx.doi.org/10.15227/orgsyn.047.0001]
[http://dx.doi.org/10.1016/S0040-4039(01)92086-6]
[http://dx.doi.org/10.1021/jo00134a022]
[http://dx.doi.org/10.1080/00397910008087139]
[http://dx.doi.org/10.1016/j.molstruc.2013.01.014]
[http://dx.doi.org/10.1246/bcsj.50.939]
[http://dx.doi.org/10.1246/cl.1978.929]
[http://dx.doi.org/10.1039/c39770000609]
[http://dx.doi.org/10.1246/cl.1979.387]
[http://dx.doi.org/10.1039/jr9540000854]
[http://dx.doi.org/10.1080/10426500701340949]
[http://dx.doi.org/10.1002/jhet.5570340411]
[http://dx.doi.org/10.1002/prac.19853270219]
[http://dx.doi.org/10.1246/cl.1982.1123]
[http://dx.doi.org/10.1021/jo00385a005]
[http://dx.doi.org/10.15227/orgsyn.051.0139]
[http://dx.doi.org/10.1021/jo01350a023]
[http://dx.doi.org/10.1021/jo01340a015]
[http://dx.doi.org/10.1021/jo1014382] [PMID: 20812755]
[http://dx.doi.org/10.1081/SCC-100104003]
[http://dx.doi.org/10.1007/s11172-012-0117-3]
[http://dx.doi.org/10.1002/anie.197805221]
[http://dx.doi.org/10.1002/cctc.201901384]
[http://dx.doi.org/10.1021/ja01124a031]
[http://dx.doi.org/10.1021/ja01299a038]
[http://dx.doi.org/10.1021/ja01480a020]
[http://dx.doi.org/10.1007/BF00635932]
[http://dx.doi.org/10.1016/0040-4020(66)80095-9]
[http://dx.doi.org/10.1002/bscb.19690780903]
[http://dx.doi.org/10.1002/jhet.5570420443]
[http://dx.doi.org/10.1021/jo101572c] [PMID: 20979420]
[http://dx.doi.org/10.1021/ed086p1422]
[http://dx.doi.org/10.1071/CH9871179]
[http://dx.doi.org/10.1038/nclimate1990]
[http://dx.doi.org/10.1017/S0021859605005708]
[http://dx.doi.org/10.1139/g99-044] [PMID: 10464789]
[http://dx.doi.org/10.1002/jhet.5570290124]
[http://dx.doi.org/10.1038/nrrheum.2015.169] [PMID: 26656660]
[http://dx.doi.org/10.1186/s12967-018-1611-7] [PMID: 30170620]
[http://dx.doi.org/10.1038/s41598-018-29604-2] [PMID: 30082828]
[http://dx.doi.org/10.1126/science.1967851] [PMID: 1967851]
[http://dx.doi.org/10.1016/j.bmc.2004.12.013] [PMID: 15698778]
[http://dx.doi.org/10.1146/annurev.pp.45.060194.002101]
[http://dx.doi.org/10.1038/sj.bjc.6605690] [PMID: 20461082]
[http://dx.doi.org/10.1038/nrd2467] [PMID: 18167490]
[http://dx.doi.org/10.1007/s10593-015-1748-8]
[http://dx.doi.org/10.1038/nrd1466] [PMID: 15286732]
[http://dx.doi.org/10.1001/archsurg.1942.01220040047005]
[http://dx.doi.org/10.1016/j.vph.2003.08.002] [PMID: 14746828]
[http://dx.doi.org/10.1007/BF02976367] [PMID: 10403135]
[http://dx.doi.org/10.1073/pnas.1700469114] [PMID: 28739897]
[PMID: 13884474]
[http://dx.doi.org/10.1105/tpc.010214] [PMID: 11752376]
[http://dx.doi.org/10.1074/jbc.M010604200] [PMID: 11134038]
[http://dx.doi.org/10.3322/caac.21492] [PMID: 30207593]
[http://dx.doi.org/10.1016/j.cbi.2008.10.060] [PMID: 19061872]
[http://dx.doi.org/10.1038/cddis.2012.141] [PMID: 23059821]
[http://dx.doi.org/10.1016/j.ejmech.2012.09.006] [PMID: 23047230]
[http://dx.doi.org/10.1007/s11892-007-0038-y] [PMID: 17547842]
[http://dx.doi.org/10.1159/000235623] [PMID: 20016244]
[http://dx.doi.org/10.1152/ajprenal.00396.2007] [PMID: 18322020]
[http://dx.doi.org/10.1016/j.bmc.2014.10.008] [PMID: 25456384]
[http://dx.doi.org/10.2174/1568009033333754] [PMID: 12570657]
[http://dx.doi.org/10.1007/s12013-013-9550-7] [PMID: 23471664]
[http://dx.doi.org/10.1038/nrn919] [PMID: 12209120]
[http://dx.doi.org/10.1007/s11094-019-01978-1]