Fluorinated pyrimidine nucleosides. 1. Synthesis of a nitrogen analog of the antitumor agent 2,2'-anhydro-1-.beta.-D-arabinofuranosyl-5-fluorocytosine hydrochloride
The nitrogen-bridged compound 2,2'-anhydro-1-beta-D-arabinofuranosyl-2,4-diamino-5-fluoropyrimidinium chloride (2), an analogue of the antitumor agent anhydro-ara-FC (1), has been synthesized. 5-Fluorocytidine was converted into 1-beta-D-ribofuranosyl-2,4-diamino-5-fluoropyrimidinium chloride (...
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Published in | Journal of medicinal chemistry Vol. 20; no. 3; pp. 344 - 348 |
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Main Author | |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
01.03.1977
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Subjects | |
Online Access | Get full text |
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Summary: | The nitrogen-bridged compound 2,2'-anhydro-1-beta-D-arabinofuranosyl-2,4-diamino-5-fluoropyrimidinium chloride (2), an analogue of the antitumor agent anhydro-ara-FC (1), has been synthesized. 5-Fluorocytidine was converted into 1-beta-D-ribofuranosyl-2,4-diamino-5-fluoropyrimidinium chloride (4), but cyclization of 4 was not achieved due to a competing side reaction. The nitrogen bridge was therefore introduced by cyclization of 5-fluoroisocytidine (10) to give the 2,2'-imino-bridged compound 16. The latter was converted into 2 by the standard procedure of thiation, S-methylation, and treatment with ammonia. Compound 2, as well as a number of the synthetic intermediates, was tested for activity against S180 sarcoma in mice. None of the new compounds exhibited any antitumor activity. |
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Bibliography: | istex:8275B6A586774D712C60C0C03241597567848C86 ark:/67375/TPS-JXC5CM8F-R |
ISSN: | 0022-2623 1520-4804 |
DOI: | 10.1021/jm00213a006 |