TY - JOUR
T1 - Synthesis and biological activities of aldose reductase inhibitors bearing acyl benzenesulfonamides as carboxylic acid surrogates
AU - Donkor, Isaac O.
AU - Abdel-Ghany, Yasser S.
AU - Kador, Peter F.
AU - Mizoguchi, Tadashi
AU - Bartoszko-Malik, Anita
AU - Miller, Duane D.
PY - 1998/1
Y1 - 1998/1
N2 - 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.
AB - 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.
KW - Acyl benzenesulfonamide
KW - Aldose reductase inhibitor
KW - Alrestatin
KW - Carboxylic acid surrogate
KW - Diabetic complication
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U2 - 10.1016/S0223-5234(99)80071-3
DO - 10.1016/S0223-5234(99)80071-3
M3 - Article
AN - SCOPUS:0031952440
SN - 0223-5234
VL - 33
SP - 15
EP - 22
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
IS - 1
ER -