Synthesis and biological activities of aldose reductase inhibitors bearing acyl benzenesulfonamides as carboxylic acid surrogates

Isaac O. Donkor, Yasser S. Abdel-Ghany, Peter F. Kador, Tadashi Mizoguchi, Anita Bartoszko-Malik, Duane D. Miller

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

We have synthesized alrestatin derivatives 1-11 possessing acyl benzenesulfonamide groups as surrogates for the carboxylic acid moiety of alrestatin. Most of the compounds were inactive as aldose reductase inhibitors compared to alrestatin, however, some of them demonstrated selectivity towards inhibition of rat kidney aldehyde reductase compared to rat lens aldose reductase suggesting that structural differences may exist between the carboxylic acid binding domains of these closely related enzymes. The chemoreactive derivatives 9 and l0 suggested the presence of a nucleophile(s) at the carboxylic acid binding site on aldose reductase.

Original languageEnglish (US)
Pages (from-to)15-22
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume33
Issue number1
DOIs
StatePublished - Jan 1998

Keywords

  • Acyl benzenesulfonamide
  • Aldose reductase inhibitor
  • Alrestatin
  • Carboxylic acid surrogate
  • Diabetic complication

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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