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Discovery of Novel Aldose Reductase Inhibitors Characterized by an Alkoxy‐Substituted Phenylacetic Acid Core
Author(s) -
Rakowitz Dietmar,
Gmeiner Andreas,
Matuszczak Barbara
Publication year - 2006
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200600054
Subject(s) - phenylacetic acid , aldose reductase , chemistry , stereochemistry , side chain , aldehyde reductase , alkoxy group , substituent , aldose , enzyme , enzyme inhibitor , alkyl , biochemistry , organic chemistry , glycoside , polymer
In continuation of our effort aimed towards the development of novel aldose reductase inhibitors, several phenylacetic acids bearing an alkoxy substituent in position 3 or 4, respectively, were prepared and screened. The latter represent formal ring opening products of the cyclohexylmethyloxyphenylacetic acids IIa and IIb , recently elaborated in our group. Out of these series, compounds 4aa and 4ba characterized by an n ‐heptyloxy subunit turned out to be the most potent inhibitors. Based on these unexpected results, we suggest that such an alkyl side chain acts as a useful surrogate for the 4‐bromo‐2‐fluorobenzyl residue often found in potent aldose reductase inhibitors.