- 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
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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.
- 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
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Read Online
- A thiol-thiosulfonate reaction providing a novel strategy for turn-on thiol sensing
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The first thiol-specific turn-on probe, BODIPY-TS, utilizing a thiosulfonate scaffold as the thiol recognition unit was reported. BODIPY-TS displays low toxicity, and features high sensitivity, fast response and quantitative reaction towards thiols. The structural novelty of BODIPY-TS would guide the development of novel thiol probes.
- Ge, Chunpo,Wang, Hao,Zhang, Baoxin,Yao, Juan,Li, Xinming,Feng, Weimin,Zhou, Panpan,Wang, Yawen,Fang, Jianguo
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supporting information
p. 14913 - 14916
(2015/10/06)
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- Design, synthesis and biological evaluation of novel 7-mercaptocoumarin derivatives as α1-adrenoceptor antagonists
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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
- Xie, Sai-Sai,Wang, Xiao-Bing,Li, Jiang-Yan,Kong, Ling-Yi
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- Anti-AIDS agents. Part 56: Synthesis and anti-HIV activity of 7-thia-di-O-(-)-camphanoyl-(+)-cis-khellactone (7-thia-DCK) analogs
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Two thia-DCK analogs (3a,b) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. Compound 3a showed potent anti-HIV activity with an EC50 value of 0.14 μM and a therapeutic index of 1110. However, the corresponding 6-tert-butyl-substituted compound (3b) showed no suppression. The bioassay results indicated that thia-DCK analogs merit attention as potential HIV-1 inhibitors.
- Chen, Ying,Zhang, Qian,Zhang, Beina,Xia, Peng,Xia, Yi,Yang, Zheng-Yu,Kilgore, Nicole,Wild, Carl,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
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p. 6383 - 6387
(2007/10/03)
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- Synthesis of methyl derivatives of linear and angular thienocoumarins and thiopyranocoumarins
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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.
- Rodighiero,Pastorini,Chilin,Marotto
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p. 847 - 852
(2007/10/03)
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- Synthesis of fluorescent 4-methyl-7-thiocoumaryl S-glycosides of sialic acid
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Condensation of 4-methyl-7-thiocoumarin sodium salt with methyl 5-N- acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-D-galacto-2- nonulopyranosonate (2), methyl 5-N-(O-acetylglycolyl)-4,7,8,9-tetra-O- acetyl-2-chloro-2,3,6-trideoxy-D-glyce
- Tanaka,Kai,Sun,Takayanagi,Uda,Furuhata
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p. 1844 - 1848
(2007/10/03)
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- Benzopyranone-β-D-thioxylosides and their use in therapy
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The present invention relates, by way of novel industrial products which are useful in therapy, to the benzopyranone-β-D-thioxyloside compounds of the formula STR1 in which: one of the substituents R or R' is an oxygen atom double-bonded to the corresponding cyclic carbon atom and the other is a group R1, the symbol represents a double bond conjugated to the CO group provided by one of the substituents R or R', X is a sulfur atom or an oxygen atom, R1 and R2, which are identical or different, are each a hydrogen atom, a C1 -C4 alkyl group, a halogen atom, a trifluoromethyl group or a phenyl group, it being possible for R1 and R2, taken together, to form a 7,8,9,10-tetrahydrodibenzo[b,d]pyran-6-one group or a 1,2,3,4-tetrahydro-9H-xanthen-9-one group with the benzopyranone group to which they are bonded, and Y is the hydrogen atom or an aliphatic acyl group.
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