Novel cyclourethane-derived HIV protease inhibitors: a ring-closing olefin metathesis based strategy

Bioorg Med Chem Lett. 2002 Aug 5;12(15):1993-6. doi: 10.1016/s0960-894x(02)00300-1.

Abstract

A series of novel macrocyclic urethanes incorporating a (R)-hydroxyethylamine isostere was designed and synthesized. Ring size and substituent efffects have been investigated. Cyclourethanes containing 14- to 16-membered rings exhibited low nanomolar inhibitory potencies against HIV-1 protease.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Amines / chemistry
  • Drug Design
  • HIV Protease Inhibitors / chemical synthesis*
  • HIV Protease Inhibitors / pharmacology
  • Kinetics
  • Stereoisomerism
  • Structure-Activity Relationship
  • Urethane / analogs & derivatives*
  • Urethane / chemical synthesis

Substances

  • Alkenes
  • Amines
  • HIV Protease Inhibitors
  • Urethane