Synthesis of a highly active new anti-HIV agent 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine

Bioorg Med Chem Lett. 2003 Nov 3;13(21):3775-7. doi: 10.1016/j.bmcl.2003.07.009.

Abstract

Compounds having methyl, vinyl, and ethynyl groups at the 4'-position of stavudine (d4T: 2',3'-didehydro-3'-deoxythymidine) were synthesized. The compounds were assayed for their ability to inhibit the replication of HIV in cell culture. The 4'-ethynyl analogue (15) was found to be more potent and less toxic than the parent compound stavudine.

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 / pharmacology*
  • Cells, Cultured
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Stavudine / analogs & derivatives*
  • Stavudine / chemical synthesis
  • Stavudine / chemistry*
  • Stavudine / pharmacology*
  • Structure-Activity Relationship
  • Virus Replication / drug effects

Substances

  • Anti-HIV Agents
  • 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine
  • Stavudine