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Synthesis of a library of "lead-like" ?-lactams by a one pot, four-component reaction.

ABSTRACT: The synthesis of a pilot scale library of 116 structurally diverse ?-lactams is reported. The library core structure emanates from a ?-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.

SUBMITTER: Martin KS

PROVIDER: S-EPMC3816122 | biostudies-other | 2013 Jul

REPOSITORIES: biostudies-other

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Synthesis of a library of "lead-like" γ-lactams by a one pot, four-component reaction.

Martin Kevin S KS Di Maso Michael J MJ Fettinger James C JC Shaw Jared T JT

ACS combinatorial science 20130612 7

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 ...[more]

PMID: 23682712

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