Chemical and Pharmaceutical Bulletin p. 103 - 114 (1996)
Update date:2022-08-02
Topics:
Matsumoto, Yuzo
Tsuzuki, Ryuji
Matsuhisa, Akira
Takayama, Kazuhisa
Yoden, Toru
Uchida, Wataru
Asano, Masaharu
Fujita, Shigeo
Yanagisawa, Isao
Fujikura, Takashi
Strong potassium channel-activating effects were found among a series of novel 4-substituted 3,4-dihydro-2H-1,4-benzoxazine derivatives. The key step in preparation was the nucleophilic substitution of 3,4-dihydro-2H-1,4- benzoxazine (3) with activated halogenopyridines, such as halogenopyridine N- oxides (15a-c) and the borane adduct (15d) of 4-bromopyridine. Structure- activity relationship studies identified 2-(3,4-dihydro-2,2-dimethyl-6- nitro-2H-1,4-benzoxazin-4-yl)pyridine-1-oxide (16a: YM934) as the optimal compound. This compound (16a) showed a more potent oral antihypertensive effect than cromakalim in conscious spontaneously hypertensive rats.
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