137215-27-1Relevant articles and documents
Anti-AIDS agents 84. Synthesis and anti-human immunodeficiency virus (HIV) activity of 2′-monomethyl-4-methyl- and 1′-thia-4-methyl-(3′R, 4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogs
Xu, Shi-Qing,Yan, Xin,Chen, Ying,Xia, Peng,Qian, Keduo,Yu, Donglei,Xia, Yi,Yang, Zheng-Yu,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
, p. 7203 - 7211 (2010)
In a continuing investigation into the pharmacophores and structure-activity relationship (SAR) of (3′R,4′R)-3′, 4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) as a potent anti-HIV agent, 2′-monomethyl substituted 1′-oxa, 1′-thia, 1′-sulfoxide, and 1′-sulfone analogs were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. Among them, 2′S-monomethyl-4-methyl DCK (5a)? and 2′S-monomethyl-1′-thia-4-methyl DCK (7a) exhibited potent anti-HIV activity with EC50 values of 40.2 and 39.1 nM and remarkable therapeutic indexes of 705 and 1000, respectively, which were better than those of the lead compound DCK in the same assay. In contrast, the corresponding isomeric 2′R-monomethyl-4-methyl DCK (6) and 2′R-monomethyl- 1′-thia-4-methyl DCK (8) showed much weaker inhibitory activity against HIV-1 replication. Therefore, the bioassay results suggest that the spatial orientation of the 2′-methyl group in DCK analogs can have important effects on anti-HIV activity of this compound class.
Design, synthesis and biological evaluation of novel 7-mercaptocoumarin derivatives as α1-adrenoceptor antagonists
Xie, Sai-Sai,Wang, Xiao-Bing,Li, Jiang-Yan,Kong, Ling-Yi
, p. 16 - 24 (2013/02/23)
Study on the pharmacophore model of α1-adrenoceptor (α1-AR) antagonists led to design a series of novel 7-mercaptocoumarin derivatives as α1-AR antagonists. All designed compounds have been synthesized and biologically eva
Synthesis of methyl derivatives of linear and angular thienocoumarins and thiopyranocoumarins
Rodighiero,Pastorini,Chilin,Marotto
, p. 847 - 852 (2007/10/03)
New linear and angular thienocoumarins and thiopyranocoumarins were synthesized. The key intermediates were appropriate methyl derivatives of 7- mercaptocoumarin, which were considered with chloroketones or propargyl chloride. Thioethers were cyclized under various conditions in order to determine which methods produced the best yields of the desired thienocoumarins 15, 16, 17, 18, 22, 23, 24, 27 and thiopyranocoumarins 28 and 29.