Inhibition of protein glycation by urea and thiourea derivatives of glycine/proline conjugated benzisoxazole analogue-Synthesis and structure-activity studies

Shantharam, C. S. and Suyoga Vardhan, D. M. and Suhas, R. and Sridhara, M. B. and Channe Gowda, D. (2013) Inhibition of protein glycation by urea and thiourea derivatives of glycine/proline conjugated benzisoxazole analogue-Synthesis and structure-activity studies. European Journal of Medicinal Chemistry, 60. pp. 325-332. ISSN 0223-5234

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Abstract

Synthesis of a new series of urea/thiourea derivatives of Gly/Pro conjugated benzisoxazole has been reported. Structure of the compounds was characterized by physical and spectroscopical data and has been screened for their in vitro antiglycation activity. Several compounds showed promising activity with IC50 < 5 μM compared to standard rutin (IC 50 = 41.9 μM). Further, it was found that compounds containing methoxy and bromine substituents have exerted highly potent activity. Thus, the title compounds represent novel class of potent antiglycating agents.

Item Type:	Article
Uncontrolled Keywords:	article, unclassified drug, Animals, drug synthesis, isoxazole derivative, structure activity relation, in vitro study, Dose-Response Relationship, Drug, Molecular Structure, Structure-Activity Relationship, drug potency, IC 50, oxidation, proton nuclear magnetic resonance, drug conjugation, Cattle, infrared spectrometry, thiourea derivative, urea derivative, unindexed drug, glycine, proline, rutoside, Bovine, Serum Albumin, Urea, 1 (2 bromophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethylthiourea, 1 (3 bromophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethylthiourea, 1 (3 bromophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethylurea, 1 (3 chlorophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxophenylthiourea, 1 (3 chlorophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin1 yl 2 oxoethylurea, 1 (4 bromophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethylurea, 1 (4 chlorophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethylthiourea, 1 (4 chlorophenyl) 3 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethylurea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (2 fluorophenyl)thiourea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (2 fluorophenyl)urea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (2 methoxyphenyl)thiourea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (2 methoxyphenyl)urea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (3 fluorophenyl)urea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (3 methoxyphenyl)thiourea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (3 methoxyphenyl)urea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (4 fluorophenyl)urea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (4 methoxyphenyl)thiourea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 (4 methoxyphenyl)urea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 phenylthiourea, 1 2 4 (6 fluorobenzodisoxazol 3 yl)piperidin 1 yl 2 oxoethyl 3 phenylurea, 2 4 (6 fluorobenzodisoxazol 3 yl)piperidine 1 carbonyl n phenylpyrrolidine 1 carbothioamide, 2 4 (6 fluorobenzodisoxazol 3 yl)piperidine 1 carbonyl n phenylpyrrolidine 1 carboxamide, Glycine, Isoxazoles, Proline, protein glycosylation
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	31 Oct 2019 07:44
Last Modified:	31 Oct 2019 07:44
URI:	http://eprints.uni-mysore.ac.in/id/eprint/9662

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