Pyrimidine Nucleosides. III. Reaction of Cytidine or N<SUP>4</SUP>-Acetylcytidine with Partially Hydrolyzed Phosphorus Oxychloride

5'-O-methyl derivatives of 1-.beta.-D-arabinofuranosylcytosine and 1-.beta.-D-arabinofuranosyluracil

“…It occurred to us that an unambiguous synthesis of 5 '-Omethyl-ara-C (III) might be feasible via the recently reported 5'-0-methylcytidine (I)3,4 using the procedure of Kanai,et al,6 for the conversion of cytidine to ara-C via the 2,2'anhydride. It was found that the conversion of I to II proceeded in almost 50% yield.…”

Pharmacokinetics Molecular Modification: Implications in Drug Design Evaluation

“…Cyclocytidine, effective against L-1210 leukemia (139), was synthesized from cytidine (140,141). It appeared less toxic and more effective than I administered once daily for 5 days in L-1210 leukemic mice (141).…”

“…Since pharmacokinetic studies indicate rapid loss of I to inactive metabolite oiu enzymatic deamination, the design of new antimetabolites which are more stable and potentially more effective has evolved. Cyclocytidine, effective against L-1210 leukemia (139), was synthesized from cytidine (140,141). It appeared less toxic and more effective than I administered once daily for 5 days in L-1210 leukemic mice (141).…”

A General Synthesis of 8,2′-Thioanhydropurine Nucleosides

“…Nucleophilic displacement of the cyclo-linkage leads to nucleosides modified on the sugar moiety (1-3) and sometimes on the base moiety (1,(4)(5)(6). Arabino cytidine (7,8) and cordycepin (6) are but two of the important biologically active compounds obtained from cyclonucleosides. Cyclonucleosides have even been detected as intermediates in proposed prebiotic syntheses (9,10) and have been used as intermediates in the chemical synthesis of nucleotides (1 1-13).…”

“…Hampton and Nichol (16) developed an exceedingly simple synthesis of 02,2'-anhydrouridines and other procedures have been developed for the synthesis of 5'-and 3'-cyclouridines (17)(18)(19) as well as cycloderivatives of thymidine (20,21) and cytidine (7,8,9,22). In the purine series, 'Part VI in a series on anhydronucleosides.…”