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Synthesis and properties of 2'-deoxy-8,2'-methylene-cycloadenosine |
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| Authors: | A Matsuda Y Fujisawa M Yamanaka H Tanaka T Miyasaka |
| Institution: | School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060, Japan |
| Abstract: | A method was developed to synthesize 2'-deoxy-8,2'-methylene-cycloadenosine (9) which was a new carbon-bridged cycloadenosine fixed in a high-antitorsional angle region. 3',5'-Di-O-acetyl-8-methanesulfonyl-2'-O-tosyladenosine (5) was cyclized with carbanions of malonic esters, followed by hydrolysis of the ester (7) and decarboxylation to afford 9. Compound 9 showed a positive CD band at 258 nm and was a substrate for adenosine deaminase with a Km of 3.2 × 10-4M and a Vmax of 2% of that of adenosine. |
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