Anti-AIDS agents Part 41: synthesis and anti-HIV activity of 3′,4′-di-o-(−)-camphanoyl-(+)-cis-khellactone (DCK) lactam analogues

DCK lactam analogues were synthesized and evaluated for anti-HIV activity against HIV-1 replication in H9 lymphocyte cells. 4-Methyl-DCK lactam (11a) exhibited potent anti-HIV activity with EC50 and therapeutic index values of 0.00024 μM and 119,333, respectively. Scheme 2. Synthesis of DCK lactam analogues. (a) Di-tert-butyl dicarbonate, Et3N; (b) K2OsO2(OH)4, K2CO3, K3Fe(CN)6, (DHQ)2-PYR; (c) (−)-(S)-camphanoyl chloride; (d) TFA.