ArticleBioorganic & medicinal chemistry2010
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.
Article in Bioorganic & medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed, 11 citations in OpenAlex.
- Insight on Mercapto-Coumarins: Synthesis and Reactivity.Molecules (Basel, Switzerland) · 2022Review
- Anti-AIDS agents 86. Synthesis and anti-HIV evaluation of 2',3'-seco-3'-nor DCP and DCK analogues.European journal of medicinal chemistry · 2011Article
- Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity.Bioorganic & medicinal chemistry letters · 2011Article
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Authors and funding
10 authors at 3 institutions in 3 countries.
Funding
Abstract
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 EC(50) 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.
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Registered trials
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