Studies on the Synthesis of Compounds Related to Adenosine-3', 5'-cyclic Phosphate. VI. : Synthesis and Cardiac Effects of N^6,N^6,2'-O-Trialkyl-, N^6,2'-O-Dialkyl-, and 2'-O-Alkyladenosine-3', 5'-cyclic Phosphates

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概要

• 論文の詳細を見る

• The alkylation of adenosine-3', 5'-cyclic phosphate (cAMP, 1) with alkyl bromides was investigated and various new alkylated cAMP derivatives, N^6,N^6,2'-O-trialkyl cAMPs (2), N^6,2'-O-dialkyl cAMPs (3) and 2'-O-alkyl cAMPs (4), were prepared by a one step reaction without the introduction of a protecting group into 1. Compounds (2) were synthesized from 1 by treatment with alkyl bromides in the presence of NaH or potassium tert-butoxide in dimethyl sulfoxide. Compounds (3) were also synthesized from 1 under conditinos similar to those of the synthesis of 2 except for the use of MeONa as a base. Compounds (4) were prepared from 1 by treatment with alkyl bromides in the presence of 18-crown-6 in dioxane-aqueous KOH solution. N^6,2'-O-Dibenzyl cAMP (3e) was obtained from 1 by the same method as the preparation of 4. These new alkylated derivatives were evaluated for cardiotonic activity in vitro. Some of them showed weak positive inotropic effects and strong negative chronotropic effects. Thus, the presence of the 2'-hydroxyl group seemed to be assential for the appearance of potent positive inotropic activity caused by cAMP derivatives.

• 社団法人日本薬学会の論文
• 1990-06-25

著者

• 加藤 元彦

  Research And Development Division Kikkoman Corporation

• 河田 登美枝

  Department Of Pharmacology School Of Medicine Niigata University

• 今井 純子

  Research And Development Division Kikkoman Corporation

• 片岡 茂博

  Research and Development Division, Kikkoman Corporation

• 山次 信幸

  Research and Development Division, Kikkoman Corporation

• 今井 昭一

  Department of Pharmacology, School of Medicine, Niigata University

• 片岡 茂博

  キッコーマン

• 今井 昭一

  Department Of Pharmacology School Of Medicine Niigata University

• 山次 信幸

  Research And Development Division Kikkoman Corporation

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