Synthesis of OSW-1 derivatives by site-selective acylation and their biological evaluation

Org Lett. 2014 Dec 19;16(24):6318-21. doi: 10.1021/ol503044j. Epub 2014 Dec 9.

Abstract

A strategy to site-selectively monoacylate an antitumor saponin OSW-1 was developed using an organotin reagent to rapidly access its derivatives that are useful as chemical probes. 4″-O-Acylated OSW-1 derivatives bearing a fluorophore, an alkyne tag, or biotin were prepared in good yields and were shown to maintain highly cytotoxic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Biotin / chemistry*
  • Cell Line, Tumor
  • Cholestenones / chemical synthesis*
  • Cholestenones / chemistry*
  • Humans
  • Molecular Structure
  • Saponins / chemical synthesis*
  • Saponins / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Cholestenones
  • Saponins
  • OSW 1
  • Biotin