Literature

Abstract

New phenolic and aza 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (DCK) analogs were synthesized and assayed for inhibition of HIV-1 IIIB replication in H9 lymphocytes. Compound 16, 4-methyl-1'-aza-DCK (4-methyl-aza-DCK), was less lipophilic than 4-methyl-DCK, and retained sub-micromolar anti-HIV activity with EC(50) and TI values of 0.77 microM and >42, respectively. Moreover, it showed moderately improved metabolic stability. Introduction of phenolic hydroxyl groups to 4-methyl-DCK decreased lipophilicity significantly, but did not improve metabolic stability and also decreased activity.

DOI： 10.1016/j.bmc.2006.12.013

Anti-AIDS agents 66: Syntheses and anti-HIV activity of phenolic and aza 3′,4′-di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) derivatives

Bioorganic & Medicinal Chemistry 2007.0

Anti-aids agents 33.1 Synthesis and anti-HIV activity of mono-methyl substituted 3′,4′-di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues

Bioorganic & Medicinal Chemistry Letters 1998.0

Anti-AIDS agents. Part 47: synthesis and anti-HIV activity of 3-substituted 3′,4′-Di-O-(S)-camphanoyl-(3′R,4′R)-(+)-cis-khellactone derivatives

Bioorganic & Medicinal Chemistry Letters 2001.0

Anti-AIDS agents-XXVIII.1 Synthesis and Anti-HIV activity of methoxy substituted 3′,4′-Di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues

Bioorganic & Medicinal Chemistry Letters 1997.0

Anti-AIDS Agents. 52. Synthesis and Anti-HIV Activity of Hydroxymethyl (3‘R,4‘R)-3‘,4‘-Di-O-(S)-camphanoyl-(+)-cis-khellactone Derivatives

Journal of Medicinal Chemistry 2004.0

Anti-AIDS agents 31.1 synthesis and anti-HIV activity of 4-substituted 3′,4′-di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) thiolactone analogs