Studies on Compounds Related to Antitumor Agents. Syntheses of 8-Substituted N6, N6-Dimethyladenosine Derivatives

• Published in: Chemical & pharmaceutical bulletin Vol. 34; no. 9; pp. 3635 - 3643
• Main Authors: KATO, TETSUO, ARAKAWA, EITARO, OGAWA, SHUICHI, SUZUMURA, YASUKO, KATO, TAKETOSHI
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1986; Maruzen; Japan Science and Technology Agency
• Subjects: antitumor activity; Carbohydrates. Nucleosides and nucleotides; Chemistry; Exact sciences and technology; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Preparations and properties; Antineoplastic agent; Acetal; Purine nucleoside; Ultraviolet spectrum; Oxidation; Ribonucleoside; NMR spectrum; Biological activity; Potassium Permanganates
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.34.3635

N6, N6-Dimethyl-8-methylsulfonyladenosine, obtained from N6, N6-dimethyl-8-methylthioadenosine by highly selective oxidation with KMnO4, was treated with cyanide ion to give 8-cyano-N6, N6-dimethyladenosine. The conversion of the cyano group to methyl imidate, methoxycarbonyl, carbamoyl, carbothioamide, and carboxylic acid moieties was achieved. These 8-substituted N6, N6-dimethyladenosines may possess resonances structures involving positions 6 and 8 in adenosine, as indicated by the spectroscopic data. They showed no antitumor activity.