Synthesis of new phorbol derivatives having ethereal side chain and evaluation of their anti-HIV activity

Bioorg Med Chem. 2005 Jul 15;13(14):4383-8. doi: 10.1016/j.bmc.2005.04.056.

Abstract

Several new phorbol derivatives having ethereal substituents at the 12-position were synthesized and subjected to biological evaluation to find new candidates of an anti-HIV agent. Among them, 12-O-(methoxymethyl)phorbol 13-decanoate showed potent inhibitory activity against infection of HIV-1 in MT-4 cells (EC50: 1.3 ng/mL) and relatively low cytotoxicity (CC50: 8.3 microg/mL). This compound was also found to have sufficient stability in mouse plasma compared with the corresponding 12-acetate derivative, which was an equipotent HIV-1 inhibitor, but with an activity that decreased considerably after plasma treatment.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Cell Line
  • Drug Evaluation, Preclinical
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Phorbols / chemical synthesis*
  • Phorbols / chemistry
  • Phorbols / pharmacology*

Substances

  • Anti-HIV Agents
  • Phorbols