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2,2-Dimethyl-3,4-dihydro-2H-1,4-benzoxazines as isosteres of 2,2-dimethylchromans acting as inhibitors of insulin release and vascular smooth muscle relaxants

Abstract

The present study describes the synthesis and biological evaluation of 4-phenylureido/thioureido-substituted 2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazines as isosteres of corresponding 2,2-dimethylchromans reported to be pancreatic β-cell KATP channel openers. The benzoxazines were found to be less active as inhibitors of the glucose-induced insulin release than their corresponding chromans, while the myorelaxant activity of some 4-arylureido-substituted benzoxazines was more pronounced than that exhibited by their chroman counterparts. The myorelaxant activity of the most potent benzoxazine 8e was further characterized on rat aortic rings precontracted by 30 mM KCl in the presence of glibenclamide (10 µM) or precontracted by 80 mM extracellular KCl. Our findings indicate that, on vascular smooth muscle cells, the benzoxazine 8e mainly behaved as a calcium entry blocker.

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Publication details

The article was received on 03 Dec 2018, accepted on 01 Feb 2019 and first published on 12 Feb 2019


Article type: Research Article
DOI: 10.1039/C8MD00593A
Citation: Med. Chem. Commun., 2019, Accepted Manuscript

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    2,2-Dimethyl-3,4-dihydro-2H-1,4-benzoxazines as isosteres of 2,2-dimethylchromans acting as inhibitors of insulin release and vascular smooth muscle relaxants

    B. Pirotte, X. Florence, E. Goffin and P. Lebrun, Med. Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C8MD00593A

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