Synthesis of a neamine dimer targeting the dimerization initiation site of HIV-1 RNA

Org Lett. 2007 Oct 25;9(22):4415-8. doi: 10.1021/ol701760k. Epub 2007 Oct 4.

Abstract

A neamine dimer designed to bind to a specific sequence of HIV-1 RNA has been synthesized. Starting from neomycin B (1), a five-step synthesis efficiently provided a key protected neamine monomer 6 (28%). From the latter, coupling reactions with activated diacids gave dimers. After deprotection, a neamine dimer was obtained as the hexachlorohydrate salt 15 with 13% overall yield over nine steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoglycosides / chemistry*
  • Aminoglycosides / pharmacology
  • Anti-HIV Agents / chemical synthesis*
  • Dimerization
  • Framycetin / chemistry*
  • Framycetin / pharmacology
  • HIV-1 / genetics*
  • Molecular Structure
  • Nucleic Acid Conformation
  • RNA, Viral / chemistry*
  • RNA, Viral / genetics*
  • Transcription Initiation Site*

Substances

  • Aminoglycosides
  • Anti-HIV Agents
  • RNA, Viral
  • Framycetin
  • neamine