A short entry to alpha-substituted gamma-alkylidene pentenolides. Synthesis and preliminary biological evaluation of novel gelastatin analogues

J Org Chem. 2009 Jan 16;74(2):703-9. doi: 10.1021/jo802082t.

Abstract

Biologically interesting 2-substituted 4-alkylidene pentenolides were prepared with complete control of regio- and stereoselectivity from 2-iodo allylic alcohols via an array of Pd-catalyzed processes, including alkynylation with methyl propiolate, tributyltin hydride addition, and alpha-functionalization. Some of the compounds possess selective cytostatic activity against ovarian carcinoma HeLa S3 and leukemia CCRF-CEM cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Cell Line, Tumor
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Palladium / chemistry
  • Propionates / chemical synthesis*
  • Propionates / chemistry
  • Propionates / pharmacology*

Substances

  • Alkenes
  • Antineoplastic Agents
  • Benzene Derivatives
  • Propionates
  • Palladium