Synthesis and anti-HIV activity of 3-alkylamido-3-deoxy-betulinic acid derivatives

Chem Pharm Bull (Tokyo). 2000 Sep;48(9):1387-90. doi: 10.1248/cpb.48.1387.

Abstract

3-Alkylamido-3-deoxy-betulinic acids were synthesized and evaluated for anti-HIV activity as part of the structure-activity relationship study of the potent anti-HIV agent 3-O-(3',3'-dimethyl)-succinyl-betulinic acid (DSB) (2). 3Alpha-diglycorylamide-3-deoxy-betulinic acid demonstrated relatively potent anti-HIV activity (EC50 0.24 microm, TI 728). However, replacing the ester group at C-3 in 2 and its analogues with an amido group yielded inactive or much less potent compounds against HIV replication, indicating that the ester group at C-3 in 2-4 is essential for potent anti-HIV activity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Betulinic Acid
  • Chromatography, High Pressure Liquid
  • HIV-1 / drug effects
  • Magnetic Resonance Spectroscopy
  • Optical Rotation
  • Pentacyclic Triterpenes
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology
  • Virus Replication

Substances

  • Anti-HIV Agents
  • Pentacyclic Triterpenes
  • Triterpenes
  • Betulinic Acid