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. 1991 Dec;39(12):3207-10.
doi: 10.1248/cpb.39.3207.

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

M Saito et al. Chem Pharm Bull (Tokyo). .

Abstract

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 (PCl5) 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 mammary 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 compound (the concentration required for 50% inhibition of cell growth, ID50 = 6.0, 15.0, 2.2 microM, respectively); the antitumor effect on P-815 cells by a total packed cell volume method showed 81.8% inhibition. The cytotoxic activity of 3 increased with the increase in alkyl chain length up to 10 carbon atoms and decreased in compounds having longer alkyl chain.

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