Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

Bioorg Med Chem. 2006 Aug 15;14(16):5651-65. doi: 10.1016/j.bmc.2006.04.034. Epub 2006 Jun 5.


Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / pharmacology
  • Colorimetry
  • HIV Integrase / metabolism*
  • Molecular Structure
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / pharmacology
  • Quinones / chemical synthesis*
  • Quinones / pharmacology
  • Stereoisomerism


  • Anti-HIV Agents
  • Naphthoquinones
  • Quinones
  • conocurvone
  • HIV Integrase