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

9 Citations (Scopus)

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

Fingerprint

Lactams

Maleic Anhydrides

Amides

Pharmaceutical Preparations

Lead

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

Cite this

Martin, K. S., Di Maso, M. J., Fettinger, J. C., & Shaw, J. T. (2013). Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction. ACS Combinatorial Science, 15(7), 356-362. https://doi.org/10.1021/co400049f

Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction. / Martin, Kevin S.; Di Maso, Michael J.; Fettinger, James C.; Shaw, Jared T.

In: ACS Combinatorial Science, Vol. 15, No. 7, 08.07.2013, p. 356-362.

Research output: Contribution to journal › Article

Martin, KS, Di Maso, MJ, Fettinger, JC & Shaw, JT 2013, 'Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction', ACS Combinatorial Science, vol. 15, no. 7, pp. 356-362. https://doi.org/10.1021/co400049f

Martin KS, Di Maso MJ, Fettinger JC, Shaw JT. Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction. ACS Combinatorial Science. 2013 Jul 8;15(7):356-362. https://doi.org/10.1021/co400049f

Martin, Kevin S. ; Di Maso, Michael J. ; Fettinger, James C. ; Shaw, Jared T. / Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction. In: ACS Combinatorial Science. 2013 ; Vol. 15, No. 7. pp. 356-362.

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Access to Document

10.1021/co400049f