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Fluorinated Pyrimidine Nucleosides. 1. Synthesis of a Nitrogen Analogue of the Antitumor Agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine Hydrochloride

Fluorinated Pyrimidine Nucleosides. 1. Synthesis of a Nitrogen Analogue of the Antitumor Agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine Hydrochloride

A F Cook

J Med Chem. 1977 Mar;20(3):344-8.

PMID: 66315

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10212256	Ancitabine hydrochloride		10212-25-6	Price

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