Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity.

Published

Journal Article

Six 3'R,4'R-di-O-(S)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) and two 3'R,4'R-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were designed, synthesized, and evaluated for inhibition of HIV-1(NL4-3) replication in TZM-bl cells. 2-Ethyl-2'-monomethyl-1'-oxa- and -1'-thia-DCP (5a, 6a), as well as 2-ethyl-1'-thia-DCP (7a) exhibited potent anti-HIV activity with EC(50) values of 30, 38 and 54 nM and therapeutic indexes of 152.6, 48.0 and 100.0, respectively, which were better than or comparable to those of the lead compound 2-ethyl-DCP in the same assay. 4-Methyl-1'-thia-DCK (8a) also showed significant inhibitory activity with an EC(50) of 128 nM and TI of 237.9.

Full Text

Duke Authors

Cited Authors

  • Liu, H-S; Xu, S-Q; Cheng, M; Chen, Y; Xia, P; Qian, K; Xia, Y; Yang, Z-Y; Chen, C-H; Morris-Natschke, SL; Lee, K-H

Published Date

  • October 1, 2011

Published In

Volume / Issue

  • 21 / 19

Start / End Page

  • 5831 - 5834

PubMed ID

  • 21871800

Pubmed Central ID

  • 21871800

Electronic International Standard Serial Number (EISSN)

  • 1464-3405

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2011.07.105

Language

  • eng

Conference Location

  • England