Selective Functionalization of Antimycin A Through an N-Transacylation Reaction

Arnaud Chevalier, Yanmin Zhang, Omar Khdour, Sidney Hecht

Research output: Contribution to journalArticle

5 Citations (Scopus)

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

Fingerprint

Antimycin A
Derivatives
Acylation
lungs
Salicylates
Poisons
Fibroblasts
Cytotoxicity
acylation
poisons
Epithelial Cells
fibroblasts
Lung
acids
cells
Adenocarcinoma of lung

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Selective Functionalization of Antimycin A Through an N-Transacylation Reaction. / Chevalier, Arnaud; Zhang, Yanmin; Khdour, Omar; Hecht, Sidney.

In: Organic Letters, Vol. 18, No. 10, 20.05.2016, p. 2395-2398.

Research output: Contribution to journalArticle

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