Synthesis of new β-lactam analogs and evaluation of their histone deacetylase (HDAC) activity

Seikwan Oh; Jae Chul Jung

doi:10.1515/znb-2007-1116

Synthesis of new β-lactam analogs and evaluation of their histone deacetylase (HDAC) activity

Seikwan Oh, Jae Chul Jung

Department of Molecular Medicine

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A simple synthesis of the β-lactams 11-13 and 16-17 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involved the O-alkylation of 6-APA and the coupling reactions of freshly prepared N-carbobenzyloxy-L-prolines 5 and 6 and 6-aminopenicillanates 8-10 and 15 in high yields. It was found that all compounds show potent growth inhibitory activity on human tumor cell lines, the most potent compound 16 exhibiting an IC₅₀ = 2.1 μM in vitro.

Original language	English
Pages (from-to)	1459-1464
Number of pages	6
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	62
Issue number	11
DOIs	https://doi.org/10.1515/znb-2007-1116
State	Published - Nov 2007

Keywords

Anticancer
Coupling reaction
Histone deacetylase
Synthesis
β-lactams

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title = "Synthesis of new β-lactam analogs and evaluation of their histone deacetylase (HDAC) activity",

abstract = "A simple synthesis of the β-lactams 11-13 and 16-17 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involved the O-alkylation of 6-APA and the coupling reactions of freshly prepared N-carbobenzyloxy-L-prolines 5 and 6 and 6-aminopenicillanates 8-10 and 15 in high yields. It was found that all compounds show potent growth inhibitory activity on human tumor cell lines, the most potent compound 16 exhibiting an IC50 = 2.1 μM in vitro.",

keywords = "Anticancer, Coupling reaction, Histone deacetylase, Synthesis, β-lactams",

author = "Seikwan Oh and Jung, {Jae Chul}",

note = "Funding Information: This work has been supported by the KOSEF Brain Neurobiology Grant (2007), by the Ewha Global Challenge (BK21) grant, and in part by Cooperative Agreement Number 1-U01 C1000211 from the Centers for Disease Control and Prevention (M. A. A.).",

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AB - A simple synthesis of the β-lactams 11-13 and 16-17 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involved the O-alkylation of 6-APA and the coupling reactions of freshly prepared N-carbobenzyloxy-L-prolines 5 and 6 and 6-aminopenicillanates 8-10 and 15 in high yields. It was found that all compounds show potent growth inhibitory activity on human tumor cell lines, the most potent compound 16 exhibiting an IC50 = 2.1 μM in vitro.

KW - Anticancer

KW - Coupling reaction

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KW - Synthesis

KW - β-lactams

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Synthesis of new β-lactam analogs and evaluation of their histone deacetylase (HDAC) activity

Abstract

Keywords

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