Exploring structure-activity relationships of transition state analogues of human purine nucleoside phosphorylase

Gary B. Evans, Richard H. Furneaux, Andrzej Lewandowicz, Vern L. Schramm, Peter C. Tyler

Research output: Contribution to journalArticle

77 Scopus citations

Abstract

The aza-C-nucleosides, Immucillin-H and Immucillin-G, are transition state analogue inhibitors of purine nucleoside phosphorylase, a therapeutic target for the control of T-cell proliferation. Immucillin analogues modified at the 2′-, 3′-, or 5′-positions of the azasugar moiety or at the 6-, 7-, or 8-positions of the deazapurine, as well as methylene -bridged analogues, have been synthesized and tested for their inhibition of human purine nucleoside phosphorylase. All analogues were poorer inhibitors, which reflects the superior capture of transition state features in the parent immucillins.

Original languageEnglish (US)
Pages (from-to)3412-3423
Number of pages12
JournalJournal of Medicinal Chemistry
Volume46
Issue number15
DOIs
StatePublished - Jul 17 2003

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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