Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams

Guido V. Janssen, Joyce A.C. van den Heuvel, Rik P. Megens, Jorg C.J. Benningshof, Huib Ovaa

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised for combinatorial library synthesis in which decoration of the scaffold is varied on both the β-lactam and the saccharine moiety. Within the European Lead Factory (ELF) consortium, a library of 263 compounds was efficiently produced using the developed methodology.
Original languageEnglish
Pages (from-to)41-49
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume26
Issue number1
DOIs
Publication statusPublished - 1 Jan 2018
Externally publishedYes

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Lactams
Microwaves
Scaffolds
Pharmaceutical Preparations
Industrial plants
Lead

Keywords

  • Library synthesis
  • Microwave synthesis
  • Saccharines
  • Staudinger reaction
  • β-Lactams

Cite this

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title = "Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams",
abstract = "Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised for combinatorial library synthesis in which decoration of the scaffold is varied on both the β-lactam and the saccharine moiety. Within the European Lead Factory (ELF) consortium, a library of 263 compounds was efficiently produced using the developed methodology.",
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Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams. / Janssen, Guido V.; van den Heuvel, Joyce A.C.; Megens, Rik P.; Benningshof, Jorg C.J.; Ovaa, Huib.

In: Bioorganic and Medicinal Chemistry, Vol. 26, No. 1, 01.01.2018, p. 41-49.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams

AU - Janssen, Guido V.

AU - van den Heuvel, Joyce A.C.

AU - Megens, Rik P.

AU - Benningshof, Jorg C.J.

AU - Ovaa, Huib

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised for combinatorial library synthesis in which decoration of the scaffold is varied on both the β-lactam and the saccharine moiety. Within the European Lead Factory (ELF) consortium, a library of 263 compounds was efficiently produced using the developed methodology.

AB - Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised for combinatorial library synthesis in which decoration of the scaffold is varied on both the β-lactam and the saccharine moiety. Within the European Lead Factory (ELF) consortium, a library of 263 compounds was efficiently produced using the developed methodology.

KW - Library synthesis

KW - Microwave synthesis

KW - Saccharines

KW - Staudinger reaction

KW - β-Lactams

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DO - 10.1016/j.bmc.2017.11.014

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JF - Bioorganic and Medicinal Chemistry

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