Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives

Jun Inoue, Ying She Cui, Osamu Sakai, Yoshikuni Nakamura, Hiromi Kogiso, Peter F Kador

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A novel series of 14 N-nitromethylsulfonanilide derivatives were synthesized and evaluated for their ability to inhibit recombinant aldose reductase. Computational docking simulations provided a good explanation for the observed structure-activity relationships. Kinetic analysis of (2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide, 11, one of the most potent compounds in this series with an IC50=0.35μM, showed uncompetitive inhibition. Subsequent in vitro culture studies of rat lenses with 11 indicated that this series of aldose reductase inhibitors are effective in either preventing or retarding sugar cataract formation associated with diabetes. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)2167-2173
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume8
Issue number8
DOIs
StatePublished - Aug 1 2000

Fingerprint

Aldehyde Reductase
Derivatives
Structure-Activity Relationship
Medical problems
Sugars
Cataract
Lenses
Inhibitory Concentration 50
Rats
Kinetics
(2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide
In Vitro Techniques

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives. / Inoue, Jun; Cui, Ying She; Sakai, Osamu; Nakamura, Yoshikuni; Kogiso, Hiromi; Kador, Peter F.

In: Bioorganic and Medicinal Chemistry, Vol. 8, No. 8, 01.08.2000, p. 2167-2173.

Research output: Contribution to journalArticle

Inoue, Jun ; Cui, Ying She ; Sakai, Osamu ; Nakamura, Yoshikuni ; Kogiso, Hiromi ; Kador, Peter F. / Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives. In: Bioorganic and Medicinal Chemistry. 2000 ; Vol. 8, No. 8. pp. 2167-2173.
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