Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue

Shijun Wen, Krystle L. Carey, Youichi Nakao, Nobuhiro Fusetani, Graham Packham, A. Ganesan

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

(Chemical Equation Presented) The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity.

Original languageEnglish
Pages (from-to)1105-1108
Number of pages4
JournalOrganic Letters
Volume9
Issue number6
DOIs
Publication statusPublished - 2007 Mar 15
Externally publishedYes

Fingerprint

Histone Deacetylase Inhibitors
Biological Products
inhibitors
affinity
Zinc
zinc
analogs
evaluation
synthesis
products
azumamide E

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue. / Wen, Shijun; Carey, Krystle L.; Nakao, Youichi; Fusetani, Nobuhiro; Packham, Graham; Ganesan, A.

In: Organic Letters, Vol. 9, No. 6, 15.03.2007, p. 1105-1108.

Research output: Contribution to journalArticle

Wen, Shijun ; Carey, Krystle L. ; Nakao, Youichi ; Fusetani, Nobuhiro ; Packham, Graham ; Ganesan, A. / Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue. In: Organic Letters. 2007 ; Vol. 9, No. 6. pp. 1105-1108.
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