Synthesis of sulfonamides and evaluation of their histone deacetylase (HDAC) activity

Seikwan Oh; Hyung In Moon; Il Hong Son; Jae Chul Jung

doi:10.3390/12051125

Synthesis of sulfonamides and evaluation of their histone deacetylase (HDAC) activity

Seikwan Oh, Hyung In Moon, Il Hong Son, Jae Chul Jung

Department of Molecular Medicine

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

20 Scopus citations

Abstract

A simple synthesis of sulfonamides 4-22 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involve N-sulfonylation of L-proline benzyl ester hydrochloride (2) and coupling reaction of N-sulfonyl chloride 3 with amines in high yields. It was found that several compounds showed good cellular potency with the most potent compound 20 exhibiting an IC₅₀ = 2.8 μM in vitro.

Original language	English
Pages (from-to)	1125-1135
Number of pages	11
Journal	Molecules
Volume	12
Issue number	5
DOIs	https://doi.org/10.3390/12051125
State	Published - May 2007

Keywords

Anticancer
Coupling reaction
HDAC
N-sulfonylation

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10.3390/12051125

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title = "Synthesis of sulfonamides and evaluation of their histone deacetylase (HDAC) activity",

abstract = "A simple synthesis of sulfonamides 4-22 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involve N-sulfonylation of L-proline benzyl ester hydrochloride (2) and coupling reaction of N-sulfonyl chloride 3 with amines in high yields. It was found that several compounds showed good cellular potency with the most potent compound 20 exhibiting an IC50 = 2.8 μM in vitro.",

keywords = "Anticancer, Coupling reaction, HDAC, N-sulfonylation",

author = "Seikwan Oh and Moon, \{Hyung In\} and Son, \{Il Hong\} and Jung, \{Jae Chul\}",

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journal = "Molecules",

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T1 - Synthesis of sulfonamides and evaluation of their histone deacetylase (HDAC) activity

AU - Oh, Seikwan

AU - Moon, Hyung In

AU - Son, Il Hong

AU - Jung, Jae Chul

PY - 2007/5

Y1 - 2007/5

N2 - A simple synthesis of sulfonamides 4-22 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involve N-sulfonylation of L-proline benzyl ester hydrochloride (2) and coupling reaction of N-sulfonyl chloride 3 with amines in high yields. It was found that several compounds showed good cellular potency with the most potent compound 20 exhibiting an IC50 = 2.8 μM in vitro.

AB - A simple synthesis of sulfonamides 4-22 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involve N-sulfonylation of L-proline benzyl ester hydrochloride (2) and coupling reaction of N-sulfonyl chloride 3 with amines in high yields. It was found that several compounds showed good cellular potency with the most potent compound 20 exhibiting an IC50 = 2.8 μM in vitro.

KW - Anticancer

KW - Coupling reaction

KW - HDAC

KW - N-sulfonylation

UR - https://www.scopus.com/pages/publications/34249898119

U2 - 10.3390/12051125

DO - 10.3390/12051125

M3 - Article

C2 - 17873846

AN - SCOPUS:34249898119

SN - 1420-3049

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EP - 1135

JO - Molecules

JF - Molecules

IS - 5

ER -

Synthesis of sulfonamides and evaluation of their histone deacetylase (HDAC) activity

Abstract

Keywords

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