Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction

Kevin S. Martin, Michael J. Di Maso, James C. Fettinger, Jared T. Shaw

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The synthesis of a pilot scale library of 116 structurally diverse γ-lactams is reported. The library core structure emanates from a γ-lactam forming one-pot, four-component reaction of ammonium acetate, p-methoxythiophenol, p-methoxybenzaldehyde, and maleic anhydride. Structural diversity then arises from amide coupling, thioaryl cleavage, N-functionalization, and heterocycle forming reactions on this core structure. Computational analysis reveals that the library contains molecular properties and shape diversity suitable for drug lead and biological probe discovery.

Original languageEnglish (US)
Pages (from-to)356-362
Number of pages7
JournalACS Combinatorial Science
Volume15
Issue number7
DOIs
Publication statusPublished - Jul 8 2013

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Keywords

  • γ-lactam
  • amide coupling
  • one-pot, four-component reaction
  • synthesis
  • thioaryl cleavage

ASJC Scopus subject areas

  • Chemistry(all)

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