title: Synthesis of novel benzoic acid derivatives with benzothiazolyl subunit and evaluation as aldose reductase inhibitors.
abstract: Several methyl benzothiazolyloxybenzoates, S-isosters, and the corresponding benzoic acids were synthesized and tested as aldose reductase inhibitors (ARIs). Out of this series, the ester derivative 2a-7 was found to exhibit the highest enzyme-inhibitoric activity. In order to investigate this unexpected result, further modifications were carried out which allowed us to explain this finding and to open a path to a novel class of ARIs.
authors.affiliation: Institute of Pharmacy, University of Innsbruck, Innsbruck, Austria. dietmar.rakowitz@uibk.ac.at
authors.forename: Dietmar
authors.initials: D
authors.lastname: Rakowitz
authors.forename: Barbara
authors.initials: B
authors.lastname: Hennig
authors.forename: Marietta
authors.initials: M
authors.lastname: Nagano
authors.forename: Stefan
authors.initials: S
authors.lastname: Steger
authors.forename: Luca
authors.initials: L
authors.lastname: Costantino
authors.forename: Barbara
authors.initials: B
authors.lastname: Matuszczak
mesh_terms: D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors*; D000818:Animals; D019817:Benzoic Acid / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D052160:Benzothiazoles; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D007908:Lens, Crystalline / Q000201:enzymology; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D052160:Benzothiazoles; D004791:Enzyme Inhibitors; D013844:Thiazoles; D019817:Benzoic Acid; D000449:Aldehyde Reductase; C005465:benzothiazole