Abstract
Pyrano- and dipyranocoumarins are classes of naturally occurring organic compounds with very interesting biological activities. This review focuses on the synthetic strategies for the synthesis of pyranocoumarins and dipyranocoumarins and the biological properties of those compounds. The synthesis involves the formation of the pyran ring, at first, from a coumarin or the formation of pyranone moiety from an existing pyran. Pyranocoumarins and dipyranocoumarins present anti-HIV, anti-cancer, neuroprotective, antidiabetic, antibacterial, antifungal, anti-inflammatory activities. Especially khellactones and calanolides are usually potent and selective in anti-HIV activity. Decursin and decursinol derivatives are effective as anticancer, neuroprotective, antidiabetic, antibacterial, and antifungal agents.
Keywords: Pyranocoumarins, dipyranocoumarins, natural products, khellactones, calanolides, decursinol derivatives, anti-HIV activity, anti-cancer activity.
Graphical Abstract
[http://dx.doi.org/10.1111/1365-3040.ep11611630]
[http://dx.doi.org/10.1002/med.10034] [PMID: 12647313]
[http://dx.doi.org/10.2174/1381612043382710] [PMID: 15579073]
[http://dx.doi.org/10.2174/0929867043363721] [PMID: 15579011]
[http://dx.doi.org/10.2174/1381612043382693] [PMID: 15579072]
[http://dx.doi.org/10.1002/cbdv.200890215] [PMID: 19089819]
[http://dx.doi.org/10.1039/C3QO00010A]
[http://dx.doi.org/10.1080/00397911.2014.926374]]
[http://dx.doi.org/10.1039/C4NP00162A] [PMID: 26151411]
[http://dx.doi.org/10.1016/j.ejmech.2017.05.004] [PMID: 28494250]
[http://dx.doi.org/10.1016/S0031-9422(97)00760-7]
[http://dx.doi.org/10.1104/pp.47.2.312] [PMID: 16657614]
[http://dx.doi.org/10.1055/s-2003-37717] [PMID: 12624830]
[http://dx.doi.org/10.1016/0031-9422(91)83459-X]
[http://dx.doi.org/10.1016/S0031-9422(00)81064-X]]
[http://dx.doi.org/10.1021/jm00093a004] [PMID: 1379639]
[http://dx.doi.org/10.1021/cr500075s] [PMID: 25303539]
[http://dx.doi.org/10.1021/acs.jnatprod.7b00579] [PMID: 29048892]
[http://dx.doi.org/10.1002/cber.19210540205]
[http://dx.doi.org/10.1021/jo061221b] [PMID: 16901178]
[http://dx.doi.org/10.1016/0040-4039(92)80027-H]
[http://dx.doi.org/10.1002/ejoc.200700885]
Duñach, E. InIII-Catalysed tandem C–C and C–O bond formation between phenols and allylic acetates. Eur. J. Org. Chem., 2010, 2010(32), 6239-6248.
[http://dx.doi.org/10.1002/ejoc.201000738]]
[http://dx.doi.org/10.1021/ol802800s] [PMID: 19117489]
[http://dx.doi.org/10.1016/j.tetlet.2010.06.058] [PMID: 20936082]
[http://dx.doi.org/10.1248/cpb.11.1042] [PMID: 5888548]
[http://dx.doi.org/10.1016/j.tet.2006.06.079]
[http://dx.doi.org/10.1016/j.ejmech.2016.06.044] [PMID: 27376493]
[http://dx.doi.org/10.1002/hlca.19730560838]
[http://dx.doi.org/10.1002/jhet.5570320136]
[http://dx.doi.org/10.1021/jo062234s] [PMID: 17288382]
[http://dx.doi.org/10.1039/B500303B] [PMID: 15834488]
[http://dx.doi.org/10.1039/c29690000970]
[http://dx.doi.org/10.1039/J39710000796]
[http://dx.doi.org/10.1021/acs.joc.5b02160] [PMID: 26525067]
[http://dx.doi.org/10.1021/np0497447] [PMID: 15679322]
[http://dx.doi.org/10.1016/j.cclet.2015.11.001]]
[http://dx.doi.org/10.1016/S0040-4020(00)01121-2]]
[http://dx.doi.org/10.1155/2014/715091]
[http://dx.doi.org/10.2174/1385272822666180530104302]
[http://dx.doi.org/10.1071/CH9712347]
[http://dx.doi.org/10.1039/p19940003251]
[http://dx.doi.org/10.1515/znb-1985-0512]
[http://dx.doi.org/10.1080/00397919008244901]
[http://dx.doi.org/10.1080/00397918808081317]
[http://dx.doi.org/10.1016/S0040-4039(00)78231-1]
[http://dx.doi.org/10.1002/jhet.5570240234]]
[http://dx.doi.org/10.3987/COM-97-7946]
[http://dx.doi.org/10.1081/SCC-200043203]
[http://dx.doi.org/10.1016/j.tetlet.2007.05.133]
[http://dx.doi.org/10.1002/hlca.19900730709]
[http://dx.doi.org/10.1021/np990241o]
[http://dx.doi.org/10.1016/j.tet.2007.07.041]
[http://dx.doi.org/10.1016/j.tetlet.2007.02.088]
[http://dx.doi.org/10.1021/jo901238y] [PMID: 19950880]
[http://dx.doi.org/10.1055/s-2003-829140]]
[http://dx.doi.org/10.1016/j.tet.2009.03.032]
[http://dx.doi.org/10.1021/jo201342m] [PMID: 21950409]
[http://dx.doi.org/10.1016/j.tetlet.2013.05.061]
[http://dx.doi.org/10.1016/S0040-4020(03)00861-5]
[http://dx.doi.org/10.1055/s-0034-1379141]
[http://dx.doi.org/10.1039/C4OB00180J] [PMID: 24740372]
[http://dx.doi.org/10.1002/ejoc.201700999]
[http://dx.doi.org/10.1002/ejoc.201001674]
[http://dx.doi.org/10.1055/s-0033-1341027]
[http://dx.doi.org/10.1016/j.tetlet.2011.06.101]
[http://dx.doi.org/10.1021/ol203229z] [PMID: 22332883]
[http://dx.doi.org/10.1039/c3cy00901g]
[http://dx.doi.org/10.1007/s11164-018-3363-7]
[http://dx.doi.org/10.1246/bcsj.62.3593]
[http://dx.doi.org/10.1055/s-2006-926329]
[http://dx.doi.org/10.1016/S0040-4039(00)88512-3]
[http://dx.doi.org/10.1016/j.bmc.2006.12.013] [PMID: 17719228]
[http://dx.doi.org/10.1016/S0040-4039(01)00642-6]
[http://dx.doi.org/10.1021/jo000861q] [PMID: 11076610]
[http://dx.doi.org/10.1039/j39690000029]
[http://dx.doi.org/10.5012/bkcs.2006.27.12.2104]]
[http://dx.doi.org/10.1016/j.tet.2006.06.032]
[http://dx.doi.org/10.1016/j.tet.2009.12.016]
[http://dx.doi.org/10.1016/j.ejmech.2004.01.003] [PMID: 15072841]
[http://dx.doi.org/10.1002/jhet.5570440304]
[http://dx.doi.org/10.1021/acs.orglett.5b02728] [PMID: 26451846]
[http://dx.doi.org/10.1016/0040-4020(78)88340-9]
[http://dx.doi.org/10.1039/p19950003135]
[http://dx.doi.org/10.1016/S0040-4039(00)73500-3]
[http://dx.doi.org/10.1016/S0040-4039(02)00428-8]
[http://dx.doi.org/10.1021/ja981142k]
[http://dx.doi.org/10.1021/jo00073a015]
[http://dx.doi.org/10.1016/00404-0399(50)1059Q-]
[http://dx.doi.org/10.1021/jm950797i] [PMID: 8632437]
[http://dx.doi.org/10.1016/0957-4166(96)00433-8]
[http://dx.doi.org/10.1021/jo00115a007]]
[http://dx.doi.org/10.1002/(SICI)1099-1344(199612)38:12<1077:AID-JLCR930>3.0.CO;2-#]]
[http://dx.doi.org/10.1016/S0040-4039(00)01820-7]
[http://dx.doi.org/10.1021/jo035753t] [PMID: 15074925]
[http://dx.doi.org/10.14233/ajchem.2013.13687]
[http://dx.doi.org/10.1080/00397919608003823]
[http://dx.doi.org/10.1002/ejoc.201701684]
[http://dx.doi.org/10.3390/molecules180911485] [PMID: 24043143]
[http://dx.doi.org/10.1021/jm00049a014] [PMID: 7525962]
[http://dx.doi.org/10.1021/np9603784] [PMID: 8792623]
[http://dx.doi.org/10.1016/S0960-894X(01)80543-6]
[http://dx.doi.org/10.1021/np50120a015] [PMID: 7545738]
[http://dx.doi.org/10.1021/jm960355m] [PMID: 9083491]
[http://dx.doi.org/10.1021/js980122d] [PMID: 9724557]
[http://dx.doi.org/10.1177/095632020201300104] [PMID: 12180648]
[http://dx.doi.org/10.1021/jm00078a001] [PMID: 7506311]
[http://dx.doi.org/10.2174/187152012803833071] [PMID: 22583405]
[http://dx.doi.org/10.1055/s-2006-957785] [PMID: 8720379]
[http://dx.doi.org/10.1055/s-2006-957701] [PMID: 9270380]
[http://dx.doi.org/10.1007/BF02976682] [PMID: 14560921]
[http://dx.doi.org/10.1186/bcr1790] [PMID: 17986353]
[http://dx.doi.org/10.1158/1535-7163.MCT-06-0231] [PMID: 17363485]
[PMID: 15705905]
[http://dx.doi.org/10.1124/mol.107.040253] [PMID: 17855653]
[http://dx.doi.org/10.1016/j.fct.2011.06.016] [PMID: 21693165]
[http://dx.doi.org/10.1371/journal.pone.0046697] [PMID: 23071615]
[http://dx.doi.org/10.1016/j.bmcl.2016.06.029] [PMID: 27329797]
[http://dx.doi.org/10.1016/j.eujim.2011.09.007]
[http://dx.doi.org/10.1093/carcin/bgp039] [PMID: 19228635]
[http://dx.doi.org/10.1016/j.leukres.2005.05.001] [PMID: 15992925]
[http://dx.doi.org/10.1080/15384047.2016.1210740] [PMID: 27414656]
[http://dx.doi.org/10.1016/j.canlet.2010.11.002] [PMID: 21122982]
[http://dx.doi.org/10.1155/2013/506324] [PMID: 23818927]
[http://dx.doi.org/10.1089/jmf.2014.3397] [PMID: 26336081]
[http://dx.doi.org/10.1021/np9800295] [PMID: 9722480]
[http://dx.doi.org/10.1021/np50106a013] [PMID: 8021652]
[http://dx.doi.org/10.3390/molecules201219738] [PMID: 26610461]
[http://dx.doi.org/10.3390/molecules18044158] [PMID: 23567363]
[http://dx.doi.org/10.1021/np049642g] [PMID: 15787438]
[http://dx.doi.org/10.1016/S0304-3835(01)00521-3] [PMID: 11410320]
[http://dx.doi.org/10.1021/np000441w] [PMID: 11374978]
[http://dx.doi.org/10.1016/S1074-7427(02)00007-2] [PMID: 12482674]
[http://dx.doi.org/10.1021/np049705v] [PMID: 15679317]
[http://dx.doi.org/10.1211/jpp.59.6.0013] [PMID: 17637179]
[http://dx.doi.org/10.1016/S0278-5846(03)00168-4] [PMID: 14687853]
[http://dx.doi.org/10.1007/s11064-015-1623-0] [PMID: 26077922]
[http://dx.doi.org/10.1002/ptr.5962] [PMID: 29193354]]
[http://dx.doi.org/10.1371/journal.pone.0074886] [PMID: 24073226]
[http://dx.doi.org/10.1002/ptr.3612] [PMID: 21972114]]
[PMID: 9475044]
[http://dx.doi.org/10.2306/scienceasia1513-1874.2008.34.317]
[PMID: 8698423]
[http://dx.doi.org/10.1016/j.bmcl.2016.06.071] [PMID: 27397496]
[http://dx.doi.org/10.1016/j.bmcl.2009.09.031] [PMID: 19811915]
[http://dx.doi.org/10.1016/j.phytochem.2004.07.001] [PMID: 15501254]
[http://dx.doi.org/10.3390/molecules14030939] [PMID: 19255552]
[http://dx.doi.org/10.1016/j.bmc.2006.02.017] [PMID: 16513358]
[http://dx.doi.org/10.1021/jm4019228] [PMID: 24694175]
[http://dx.doi.org/10.1016/S0378-8741(97)00044-5] [PMID: 9234162]
[http://dx.doi.org/10.1016/j.pestbp.2011.08.013]
[http://dx.doi.org/10.1021/np401040d] [PMID: 24597921]