122670-62-6Relevant articles and documents
Conformationally Rigid Analogues of Aldose Reductase Inhibitor, Tolrestat. Novel Syntheses of Naphthalene-Fused γ-, δ-, and ε-Lactams
Wrobel, Jay,Dietrich, Arlene,Gorham, Beverly J.,Sestanj, Kazimir
, p. 2694 - 2702 (1990)
Cyclic analogues (4-6) of tolrestat (1) and oxotolrestat (2) were prepared by employing novel synthesis routes for the formation of the required γ-, δ-, and ε-lactams.In this regard 2,3,4,5-tetrahydro-9-methoxy-1H-naphthazepin-1-one, 7, and 3,4-dihydro-8-methoxybenzisoquinolin-1(2H)-one, 8, were prepared from a common precursor, namely 2,3-dihydro-7-methoxy-4(1H)-phenanthrenone, 13, and further elaborated to compounds 4a-b and 5a-d, respectively.Compounds 6a-b were prepared from a tolrestat precursor, 5-methyl-2-methoxy-1-(trifluoromethyl)naphthalene, 35.Six- and seven-membered lactam acetic acid methyl esters, 29, resisted vigorous thioamidation condition; therefore, the corresponding thiolactam analogues 4 and 5 could not be prepared.However, thioamidation was achieved in the five-membered ring series, leading to thiolactam 6b.Lactams in the series 4 or 5 were considerably weaker than 1 or 2 as inhibitors of bovine lens aldose reductase although thiolactam 6b had high inhibitory activity.
Syntheses of tolrestat analogues containing additional substituents in the ring and their evaluation as aldose reductase inhibitors. Identification of potent, orally active 2-fluoro derivatives
Wrobel,Millen,Sredy,Dietrich,Gorham,Malamas,Kelly,Bauman,Harrison,Jones,Guinosso,Sestanj
, p. 2504 - 2520 (2007/10/02)
A series of aldose reductase inhibitors were prepared which were analogues of the potent, orally active inhibitor tolrestat (1). These compounds (5, 7, 9, and 10) have an extra substituent on one of the unoccupied positions on the naphthalene ring of 1. P
N-acyl-N-naphthoylglycines as aldose reductase inhibitors
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, (2008/06/13)
Disclosed herein are N-acyl-N-naphthoylglycines and methods of their preparation. The N-acyl-N-naphthoylglycines are novel aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
