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)

Access to Document

10.1021/co400049f

Cite this

@article{4d64aa086eb94c969be10517cac1bcda,

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

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.",

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

author = "Martin, {Kevin S.} and {Di Maso}, {Michael J.} and Fettinger, {James C.} and Shaw, {Jared T.}",

year = "2013",

month = jul,

day = "8",

doi = "10.1021/co400049f",

language = "English (US)",

volume = "15",

pages = "356--362",

journal = "Journal of Combinatorial Chemistry",

issn = "2156-8952",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Synthesis of a Library of "lead-Like" γ-Lactams by a One Pot, Four-Component Reaction

AU - Martin, Kevin S.

AU - Di Maso, Michael J.

AU - Fettinger, James C.

AU - Shaw, Jared T.

PY - 2013/7/8

Y1 - 2013/7/8

N2 - 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.

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.

KW - γ-lactam

KW - amide coupling

KW - one-pot, four-component reaction

KW - synthesis

KW - thioaryl cleavage

UR - http://www.scopus.com/inward/record.url?scp=84880069988&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880069988&partnerID=8YFLogxK

U2 - 10.1021/co400049f

DO - 10.1021/co400049f

M3 - Article

C2 - 23682712

AN - SCOPUS:84880069988

VL - 15

SP - 356

EP - 362

JO - Journal of Combinatorial Chemistry

JF - Journal of Combinatorial Chemistry

SN - 2156-8952

IS - 7

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this