Selective Irreversible Inhibitors of Aldose Reductase

Michael W. Smar, Jeffrey J. Ares, Duane D. Miller, Toshihiro Nakayama, Hiroyuki Itabe, Peter F. Kador

Research output: Contribution to journalArticlepeer-review

18 Scopus citations


A series of 5-substituted-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid analogues have been examined as irreversible inhibitors of aldose reductase. The 5-α-bromoacetamide and 5-α-iodoacetamide analogues 5 and 6 gave irreversible inhibition of aldose reductase while the 5-α-chloroacetamide analogue 3 did not show this type of inhibition. Protection studies indicate that irreversible inhibitions are occurring at the inhibitor binding site. Comparative irreversible inhibition studies with rat lens aldose reductase (RLAR) and rat kidney aldehyde reductase (RKALR) indicate that 5-α-haloacetamide analogues 5 and 6 are much more effective inhibitors of RLAR.

Original languageEnglish (US)
Pages (from-to)1117-1120
Number of pages4
JournalJournal of Medicinal Chemistry
Issue number6
StatePublished - Mar 1 1992

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


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