1989
DOI: 10.1248/cpb.37.2398
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Synthesis and aldose reductase-inhibitory activity of benzo(b)furan derivatives possessing a carboxymethylsulfamoyl group.

Abstract: Various benzo[b]furan derivatives with a carboxymethylsulfamoyl group were prepared and evaluated for aldose reductase-inhibitory potency. Most of the compounds displayed significant inhibitory activities (IC50, 10(-8)-10(-7) M). Among the test compounds, the compounds having a carboxymethylsulfamoyl group at the 3- or 4-position exhibited the greatest inhibitory potency. Structure-activity trends of the tested compounds are discussed.

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Cited by 9 publications
(3 citation statements)
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“…The 2-pyrazoly-(8), 2-isoxazolyl-(12), 2-oxadiazolylbenzo [b] furans (15,(17)(18)(19) were inactive (Tables 1, 2). Unfortunately, inhibitory activity of the carboxylic acids (6c, e, 21k) could not be determined, because they are fluorescent compounds.…”
Section: Preparation Of 2-isoxazolylbenzo[b] Furans (9-12)mentioning
confidence: 99%
“…The 2-pyrazoly-(8), 2-isoxazolyl-(12), 2-oxadiazolylbenzo [b] furans (15,(17)(18)(19) were inactive (Tables 1, 2). Unfortunately, inhibitory activity of the carboxylic acids (6c, e, 21k) could not be determined, because they are fluorescent compounds.…”
Section: Preparation Of 2-isoxazolylbenzo[b] Furans (9-12)mentioning
confidence: 99%
“…Bromination of 2-acetyl-7-hydroxybenzo [b]furan (1a) 14 with NBS in an equivalent amount and 2 equivalent amounts in the presence of AlCl 3 gave the 4-bromo compound (1b) 15 and the 4,6-dibromo compound (1c), respectively. Alkylation of 1 with various alkyl halides afforded the corresponding 7alkyloxybenzo [b]furans (2a-2q) (Table S1, ESI †).…”
Section: Chemistrymentioning
confidence: 99%
“…Treatment of 2a with phosphonoamides (5) 12 under Horner-Wadsworth-Emmons (HWE) reaction 13 conditions afforded (E/Z)-2-(2-alkylcarbamoyl-1-methylvinyl)benzo [b]furans ((E/ Z)-3a, -3b, -3c). Compounds 2b, 2c and 2f 14 were also subjected to HWE reaction with the phosphonoamide (5) to give (E/Z)-2-(2-alkylcarbamoyl-1-methylvinyl)benzo [b]furans ((E/Z)-3d, -3e and -3f), respectively. Yields and ratios of E/Z of 3 are shown in Scheme 1.…”
mentioning
confidence: 99%