Anti-AIDS agents 72. Bioisosteres (7-carbon-DCKs) of the potent anti-HIV lead DCK

Bioorg Med Chem Lett. 2007 Aug 1;17(15):4316-9. doi: 10.1016/j.bmcl.2007.05.026. Epub 2007 May 16.

Abstract

Three 9,10-di-O-(-)-camphanoyl-7,8,9,10-tetrahydro-benzo[h]chromen-2-one (7-carbon-DCK) analogs (3a-c) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. All three new carbon bioisosteres of the anti-HIV lead DCK showed anti-HIV activity. Compound 3a had an EC(50) value of 0.068 microM, which was comparable to that of DCK in the same assay. The preliminary results indicated that 7-carbon-DCK analogs merit attention as potential HIV-1 inhibitors for further development into clinical trials candidates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Camphor / analogs & derivatives*
  • Camphor / chemistry
  • Camphor / pharmacology
  • Cells, Cultured
  • HIV-1 / drug effects
  • HIV-1 / physiology
  • Humans
  • Lactones / chemistry
  • Lactones / pharmacology*
  • Virus Replication / drug effects

Substances

  • 3'R,4'R-di-O-(-)-camphanoyl-(+)-cis-khellactone
  • Anti-HIV Agents
  • Lactones
  • Camphor