Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-[(1H-Benzimidazol-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate, an H^+/K^+-ATPase Inhibitor, Based on Its Reaction with Thiols
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概要
- 論文の詳細を見る
To explore the mechanism of the gastric antisecretion activity of ethyl 2-[(1H-benzimidazol-2-yl)sulfinylmethyl]-4-dimethylamino-5-pyrimidinecarboxylate (5), a potential H^+/K^+-ATPase inhibitor, in the acid compartment of parietal cells, its reaction with some alkylthiols in the presence of hydrochloric acid was investigated. Upon treatment with 2-mercaptoethanol under acidic conditions, 5 gave a characteristic 1 : 2 adduct, ethyl 4-[2-(2-hydroxyethyldithio)-1-(2-hydroxyethylthio)ethylidenamino]pyrimido[1,2-α]benzimidazole-3-carboxylate (6), instead of providing a disulfide of type 3,2-(2-alkyldithiomethylpyridino)benzimidazolide, the product predicted to be formed according to the reaction mechanism of common H^+/K^+-ATPase inhibitors, such as omeprazole or lansoprazole, with mercaptans.With a large excess of 2-mercaptoethanol, 5 provided 2-(2-hydroxyethylthio)-1H-benzimidazole (8) and ethyl 4-dimethylamino-2-(2-hydroxyethyldithio)-5-pyrimidinecarboxylate (9) as well as 6. The transformation mechanisms and their implications are discussed.
- 公益社団法人日本薬学会の論文
- 1995-11-15
著者
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村岡 修
Faculty of Pharmaceutical Sciences, Kinki University
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村岡 修
Faculty Of Pharmaceutical Sciences Kinki University
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寺島 幸司
Research Laboratories, Roussel Morishita Co., Ltd.,
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小野 勝
Faculty of Pharmaceutical Sciences, Kinki University
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小野 勝
Faculty Of Pharmaceutical Sciences Kinki University
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Ono Masaru
Faculty Of Pharmaceutical Sciences Kinki University
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Muraoka O
Shonai Regional Center For Plant Biotechnol. Yamagata
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寺島 幸司
Research Laboratories Roussel Morishita Co. Ltd.
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