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

doi:10.1021/co400049f

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	356-362
Number of pages	7
Journal	ACS Combinatorial Science
Volume	15
Issue number	7
DOIs	https://doi.org/10.1021/co400049f
State	Published - Jul 8 2013

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

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10.1021/co400049f

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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.",

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AU - Martin, Kevin S.

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AU - Shaw, Jared T.

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AB - 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.

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KW - thioaryl cleavage

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

Abstract

Keywords

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