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 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 languageEnglish (US)
Pages (from-to)356-362
Number of pages7
JournalACS Combinatorial Science
Volume15
Issue number7
DOIs
StatePublished - 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

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 journalArticle

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.
@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 = "7",
day = "8",
doi = "10.1021/co400049f",
language = "English (US)",
volume = "15",
pages = "356--362",
journal = "ACS Combinatorial Science",
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

VL - 15

SP - 356

EP - 362

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

SN - 2156-8952

IS - 7

ER -