Selective Functionalization of Antimycin A Through an N-Transacylation Reaction

Arnaud Chevalier, Yanmin Zhang, Omar Khdour, Sidney Hecht

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Acylation of 3-(N-formylamino)salicylic acids resulted in transacylation with loss of the formyl moiety. The reaction proceeds through a bis-N-acylated intermediate, which undergoes facile deformylation. This transacylation reaction has been employed for the site-specific functionalization of the mitochondrial poison antimycin A, affording several novel derivatives. The selective cytotoxicity of some of these derivatives toward cultured A549 human lung epithelial adenocarcinoma cells, in comparison with WI-38 normal human lung fibroblasts, illustrates one application of this transacylation reaction.

Original languageEnglish (US)
Pages (from-to)2395-2398
Number of pages4
JournalOrganic Letters
Volume18
Issue number10
DOIs
StatePublished - May 20 2016

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Fingerprint Dive into the research topics of 'Selective Functionalization of Antimycin A Through an N-Transacylation Reaction'. Together they form a unique fingerprint.

  • Cite this