Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors

Seikwan Oh; Hyung In Moon; Jae Chul Jung

doi:10.1515/znb-2008-1108

Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors

Seikwan Oh, Hyung In Moon, Jae Chul Jung

Department of Molecular Medicine

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

2 Scopus citations

Abstract

A simple synthesis, involving a key coupling reaction, and the biological activity of the title compounds 16 and 17 are described. The key fragments are the amine·HCl salt 6 and the acids 9 and 13, which were smoothly coupled by using ethyl(dimethylaminopropyl)carbodiimide (EDCI) and 1- hydroxybenzotriazole (HOBt) in high yield. We have found that the in vitro growth inhibitory potency of the new compounds 16 and 17 exhibits good histone deacetylase (HDAC) activity.

Original language	English
Pages (from-to)	1300-1304
Number of pages	5
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	63
Issue number	11
DOIs	https://doi.org/10.1515/znb-2008-1108
State	Published - 2008

Keywords

4-Oxopiperidine-1-carboxylate
4-Oxopyrrolidine-1-carboxylate
Acetylation
Coupling synthesis

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Oh, S., Moon, H. I., & Jung, J. C. (2008). Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 63(11), 1300-1304. https://doi.org/10.1515/znb-2008-1108

Oh, Seikwan ; Moon, Hyung In ; Jung, Jae Chul. / Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors. In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences. 2008 ; Vol. 63, No. 11. pp. 1300-1304.

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title = "Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors",

abstract = "A simple synthesis, involving a key coupling reaction, and the biological activity of the title compounds 16 and 17 are described. The key fragments are the amine·HCl salt 6 and the acids 9 and 13, which were smoothly coupled by using ethyl(dimethylaminopropyl)carbodiimide (EDCI) and 1- hydroxybenzotriazole (HOBt) in high yield. We have found that the in vitro growth inhibitory potency of the new compounds 16 and 17 exhibits good histone deacetylase (HDAC) activity.",

keywords = "4-Oxopiperidine-1-carboxylate, 4-Oxopyrrolidine-1-carboxylate, Acetylation, Coupling synthesis",

author = "Seikwan Oh and Moon, {Hyung In} 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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doi = "10.1515/znb-2008-1108",

language = "English",

volume = "63",

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Oh, S, Moon, HI & Jung, JC 2008, 'Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors', Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, vol. 63, no. 11, pp. 1300-1304. https://doi.org/10.1515/znb-2008-1108

Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors. / Oh, Seikwan; Moon, Hyung In; Jung, Jae Chul.

In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 63, No. 11, 2008, p. 1300-1304.

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

TY - JOUR

T1 - Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors

AU - Oh, Seikwan

AU - Moon, Hyung In

AU - Jung, Jae Chul

N1 - 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.).

PY - 2008

Y1 - 2008

N2 - A simple synthesis, involving a key coupling reaction, and the biological activity of the title compounds 16 and 17 are described. The key fragments are the amine·HCl salt 6 and the acids 9 and 13, which were smoothly coupled by using ethyl(dimethylaminopropyl)carbodiimide (EDCI) and 1- hydroxybenzotriazole (HOBt) in high yield. We have found that the in vitro growth inhibitory potency of the new compounds 16 and 17 exhibits good histone deacetylase (HDAC) activity.

AB - A simple synthesis, involving a key coupling reaction, and the biological activity of the title compounds 16 and 17 are described. The key fragments are the amine·HCl salt 6 and the acids 9 and 13, which were smoothly coupled by using ethyl(dimethylaminopropyl)carbodiimide (EDCI) and 1- hydroxybenzotriazole (HOBt) in high yield. We have found that the in vitro growth inhibitory potency of the new compounds 16 and 17 exhibits good histone deacetylase (HDAC) activity.

KW - 4-Oxopiperidine-1-carboxylate

KW - 4-Oxopyrrolidine-1-carboxylate

KW - Acetylation

KW - Coupling synthesis

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Oh S, Moon HI, Jung JC. Convenient synthesis and evaluation of biological activity of benzyl (2S)-2-[(R)-1-hydroxy-2-oxo-(1-phenethyl)prop-3-ylcarbamoyl]-4-oxopiperidine- (or -4-oxopyrrolidine)-1-carboxylate as novel histone deacetylase inhibitors. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences. 2008;63(11):1300-1304. doi: 10.1515/znb-2008-1108