Novel Histamine H_3 Receptor Antagonists : Synthesis and Evaluation of Formamidine and S-Methylisothiourea Derivatives

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概要

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• In order to obtain a new, potent and selective histamine H_3 receptor antagonist, chemical modifications of thioperamide, a well-known H_3 receptor antagonist, were conducted. A new series of compounds has een synthesized by modifying the thiourea and cyclohexyl groups of thioperamide, and tested for H_3 receptor affinity by receptor binding assay using plasma membrane from rat cerebral cortex. The thiourea group of thioperamide was found to be replaceable with a basic moiety such as formamidine or S-methylisothiourea. Replacement of the cyclohexyl group in thioperamide by a 1-adamantyl or an exo-2-norbornyl group increased the affinity for H_3 receptor. Among the compounds synthesized, N-(1-adamantyl)-N', N'-[3-(4(5)-1H-imidazolyl)pentamethylene]formamidine 3f (AQ0145) showed the highest H_3 receptor affinity, having a potent antagonistic activity. This compound was at least 1000-fold more active towards H_3 than towards H_1 and H_2 receptors.

• 公益社団法人日本薬学会の論文
• 1997-02-15

著者

• 村上 和夫

  阪大院薬

• 近藤 俊哉

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 後藤 隆雄

  トーアエイヨー株式会社

• Kondo T

  Research Division The Green Cross Corporation

• Goto Takaaki

  Faculty Of Pharmaceutical Sciences Tohoku University

• Goto T

  トーアエイヨー

• Fukaya C

  Yoshitomi Pharmaceutical Ind. Ltd. Osaka Jpn

• Fukaya Chikara

  Quality Control Production Division Yoshitomi Pharmaceutical Industries Ltd.

• Fukaya Chikara

  Research Division The Green Cross Corporation

• Sugiura M

  Research Division The Green Cross Corporation

• Goto T

  Hokuriku Univ. Kanazawa Jpn

• Murakami K

  Osaka Univ. Osaka Jpn

• Murakami K

  阪大院薬

• SAKASHITA Hiroshi

  Research Division, The Green Cross Corporation

• GOTO Tomokazu

  Research Division, The Green Cross Corporation

• MUARKAMI Kazuki

  Research Division, The Green Cross Corporation

• SUGIURA Masanori

  Research Division, The Green Cross Corporation

• KONDO Takao

  Research Division, The Green Cross Corporation

• Sakashita H

  Yamanouchi Pharmaceutical Co. Ltd. Ibaraki Jpn

• Sakashita Hiroshi

  Research Division The Green Cross Corporation

• Murakami Kazuki

  Research Division, The Green Cross Corporation

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