Studies on the Synthesis of COmpounds Related to Adenosine 3', 5'-Cyclic Phosphate. IX. Synthesis and Cytotoxic Effect of Adenosine 3', 5'-Cyclic Alkylphosphoramidates

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概要

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• A series of adenosine 3', 5'-cyclic monophosphoramidates (3,cAMP amidates), including long-chain alkyl amidates, were synthesized from adenosine 3', 5'-cyclic monophosphate (1,cAMP) by means of a one-pot reaction. THis reaction proceeded by the treatment of cAMP tributylammonium salt (2) with phosphorus pentachloride (PCl_5) and alkylamine in N, N-dimethylformamide (DMF). Compounds 3 synthesized were investigated to determine their cytotoxic activities on the growth of mouse mastocytoma P-815 cells, mouse manamary tumor FM3A cells, and human mammary tumor ZR-75 cells in culture. It was found that compounds 3h-m showed significant cytotoxic activities against these cell lines, and that cAMP decylamidate (3j) was the most cytotoxic compounds (the concentration required for 50% inhibition of cell growth, ID_<50>=6.0,15.0,2.2 μM, respectively); the antitumor effect on P-815 cells by a total packed cell volume method showed 81.8% inhibition. The cytotoxic activity of 3 increaesd with the increase in alkyl chain length up to 10 carbon atoms and decreased in compounds having longer alkyl chain.

• 公益社団法人日本薬学会の論文
• 1991-12-25

著者

• 片岡 茂博

  Research and Development Division, Kikkoman Corporation

• 山次 信幸

  Research and Development Division, Kikkoman Corporation

• 市川 厚

  Department of Health Chemistry, Faculty of Pharmaceutical Sciences, Kyoto University

• 片岡 茂博

  キッコーマン

• 市川 厚

  Department Of Health Chemistry Faculty Of Pharmaceutical Sciences Kyoto University

• 斉藤 眞

  Noda Institute For Scientific Research

• 那須 綾子

  Research and Development Division, Kikkoman Corp.

• 那須 綾子

  Research And Development Division Kikkoman Corp.

• 山次 信幸

  Research And Development Division Kikkoman Corporation

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