Synthesis and Biological Study of the Cyclopentenyl Carbocyclic Nucleoside Analogue of 5-Azacytidine |
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| Authors: | Benjamin B. Lim Victor E. Marquez Kathryn A. Dobyns David A. Cooney Erik De Clercq |
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| Affiliation: | 1. Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, Division of Cancer Treatment , National Cancer Institute, National Institutes of Health , Bethesda, MD, 20892;2. Rega Institute for Medical Research, Katholieke Universiteit Leuven , B-3000, Leuven, Belgium |
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| Abstract: | Abstract Cyclopentenyl cytosine (CPE-C, 3) possesses excellent antitumor and antiviral activity. The synthesis of the analogous cyclopentenyl triazine nucleoside, 5-aza-CPE-C (4), was accomplished by a novel approach that utilized a key 1-cyclopentenyl-4-methylisobiuret intermediate (7) produced from the corresponding cyclopentenylamine 5. 5-Aza-CPE-C was more than six-hundred times less potent than CPE-C both in its capacity to reduce CTP levels as well as in its antitumor and antiviral activity. |
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