Synthesis and Enzymatic Activity of Adenosine 3', 5'-Cyclic Phosphate Analogs

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概要

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• 2-Mono-and 2,6-di-substituted cAMP (cAMP : adenosine 3', 5'-cyclic phosphate) were derived from the corresponding adenosine analogs via the 5'-phosphates. 2-Substituted cAMP and aristeromycin 3', 6'-cyclic phosphate were led to the 8-bromo derivatives. 8-(3,5-Dimethylpyrazol-1-yl)-cAMP was derived from 8-hydrazinoadenosine. 8-(2-Hydroxypropyl-2)-cAMP was prepared by a γ-ray irradiation of cAMP in isopropanol. N^6-Butyl-2-phenyl-cAMP was derived from 2-phenylinosine. 2-or 8-Substituted cAMP was led to its dibutyryl derivative. The activities of these new analogs were assessed with cAMP-dependent protein kinases (PK) and cAMP phosphodiesterases (PDE). 8-Bromo-2-chloro-, 2-chloro-, 2-bromo-, 2-phenylthio-, 8-carbamoyl- and 8-carboxy-cAMP were better activators of PK than cAMP, while 2-substituted analogs were significant substrates and inhibitors of PDE. 2-Phenyl-, benzyl-, phenoxy-, chloro- and bromo-cAMP or aristeromycin 3', 6'-cyclic phosphate had an inhibitory effect on the binding of cAMP to PK equal to or more than cAMP.

• 社団法人日本薬学会の論文
• 1979-04-25

著者

• 牧 良孝

  武田薬品工業株式会社中央研究所

• 丸本 龍二

  Central Research Laboratories Takeda Chemical Industries Ltd.

• 鈴木 剛

  Central Research Division, Takeda Chemical Industries, Ltd.

• 本庄 美喜男

  Central Research Division, Takeda Chemical Industries, Ltd.

• 宮下 修

  Central Research Division, Takeda Chemical Industries, Ltd.

• 吉岡 義夫

  Central Research Division Takeda Chemical Ind. Ltd.

• 本庄 美喜男

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• 宮下 修

  Central Research Division Takeda Chemical Industries Ltd.

• 鈴木 剛

  Central Research Division Takeda Chemical Industries Ltd.

• 牧 良孝

  武田薬品工業中研

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