Synthesis of Pyrazolone Derivatives. XXXVI. Synthetic and Pharmacological Studies on (4S, 7R)-4,7-Methano-1H (or 2H)-indazoles and indazolium Compounds

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概要

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• (4S, 7R)-1 and 2-substituted-4,7-methanoindazoles were synthesized. The nucleophilic reaction of substituted hydrazines with (1R, 4S)-3-hydroxymethylenebornane-2-one (1) gave corresponding (4S, 7R)-1-substituted-4,7-methano-1H-indazoles (3). Attempts to synthesize 2-substituted-4,7-methanoindazoles starting from (1R, 4S)-3-acetoxymethylenebornane-2-one (5a) were unsuccessful. Quarternization of (4S, 7R)-4,7-methanoindazole (3a) afforded (4S, 7R)-4,7-methano-1H-indazolium compounds (8,9 and 10a, b). (4S, 7R)-2-Substituted-4,7-methanoindazoles (11 and 12) were successfully obtained by the reaction of 3a with acetic anhydride and hydroxylamine-O-sulfonic acid. The structure assignments of the 1 and 2-substituted compounds were made on the basis of their NMR spectra. Pharmacological profiles of newly synthesized compounds were studied in vivo and in vitro. The behavioral symptoms of mice treated with compounds 10a and 10b were serious abnormal gait and catalepsy. The in vitro studies on isolated ileum preparation and isolated heart preparation suggested that compound 10b has effective anticholinergic and antihistaminergic actions.

• 公益社団法人日本薬学会の論文
• 1979-08-25

著者

• 織田 範一

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 伊藤 磯雄

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 伊藤 磯雄

  名古屋市立大学薬学部

• 織田 範一

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 伊藤 磯雄

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 工藤 佳久

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 工藤 佳久

  Faculty Of Pharmaceutical Sciences Nagoya City University:(present Address) Laboratory Of Pharmacolo

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