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

doi:10.1016/j.bmc.2017.11.014

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 Journal › Article › Academic › peer-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 language	English
Pages (from-to)	41-49
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	26
Issue number	1
DOIs	https://doi.org/10.1016/j.bmc.2017.11.014
Publication status	Published - 1 Jan 2018
Externally published	Yes

Keywords

Library synthesis
Microwave synthesis
Saccharines
Staudinger reaction
β-Lactams

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http://www.mendeley.com/research/microwaveassisted-diastereoselective-twostep-threecomponent-synthesis-rapid-access-druglike-librarie

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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.",

keywords = "Library synthesis, Microwave synthesis, Saccharines, Staudinger reaction, β-Lactams",

author = "Janssen, {Guido V.} and {van den Heuvel}, {Joyce A.C.} and Megens, {Rik P.} and Benningshof, {Jorg C.J.} and Huib Ovaa",

year = "2018",

month = jan,

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doi = "10.1016/j.bmc.2017.11.014",

language = "English",

volume = "26",

pages = "41--49",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

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

Research output: Contribution to Journal › Article › Academic › peer-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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M3 - Article

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SP - 41

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IS - 1

ER -

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

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Keywords

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