| Fluorinated Pyrimidine nucleosides. 1. Synthesis of a nitrogen analogue of the antitumor agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine hydrochloride. | |
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MedLine Citation:
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PMID: 66315 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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A F Cook |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 20 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1977 Mar |
Date Detail:
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Created Date: 1977-05-12 Completed Date: 1977-05-12 Revised Date: 2003-11-14 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 344-8 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Ancitabine
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analogs & derivatives*,
chemical synthesis,
therapeutic use Animals Antineoplastic Agents / chemical synthesis*, therapeutic use Cytarabine / analogs & derivatives* Methods Mice Models, Molecular Molecular Conformation Sarcoma, Experimental / drug therapy |
| Chemical | |
Reg. No./Substance:
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0/Antineoplastic Agents; 147-94-4/Cytarabine; 31698-14-3/Ancitabine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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