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. 2007 May 24;12(5):1125-35.
doi: 10.3390/12051125.

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

Seikwan Oh  1 , Hyung-In Moon, Il-Hong Son, Jae-Chul Jung, Mitchell A Avery
Affiliations

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

Seikwan Oh et al. Molecules. .

Erratum in

  • Molecules. 2009;14(5):1950-1. Avery, Mitchell A [added]

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 microM in vitro.

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Figures

Scheme 1
Scheme 1
Synthesis of sulfonamides 4–7.
Scheme 2
Scheme 2
Synthesis of PMB amine 10.
Scheme 3
Scheme 3
Synthesis of sulfonamides 11–22.
See this image and copyright information in PMC

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