Methylenebis(sulfonamide) linked nicotinamide adenine dinucleotide analogue as an inosine monophosphate dehydrogenase inhibitor

Liqiang Chen, Guangyao Gao, Laurent Bonnac, Daniel J. Wilson, Eric M. Bennett, Hiremagalur N. Jayaram, Krzysztof W. Pankiewicz

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

A methylenebis(sulfonamide) linked NAD analogue has been designed to circumvent the metabolically unstable, ionic nature of the natural pyrophosphate linkage. This NAD analogue is assembled through two Mitsunobu reactions of a methylenebis(sulfonamide) linker with two protected nucleosides. A 2,4-dimethoxybenzyl group is used as a sulfonamide protective group, which allows facile removal under mildly acidic conditions. This NAD analogue inhibits IMPDH at low micromolar concentration.

Original languageEnglish (US)
Pages (from-to)3152-3155
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number11
DOIs
StatePublished - Jun 1 2007

Bibliographical note

Funding Information:
These studies were funded by the Center for Drug Design, University of Minnesota, and USDOD ARMY Grant W81XWH-05-01-0216.

Keywords

  • IMPDH
  • Inosine monophosphate dehydrogenase
  • Methylenebis(sulfonamide)
  • NAD analogue
  • Pyrophosphate mimics

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