Deoxy cytidine

Therapeutic Function Antineoplastic, Antiviral Chemical Name Cytidine, 2 -deoxy-2, 2 -difluoro Common Name Difluorodeoxycytidine Gemcitabine Structural Formula ... 

Cycloprotobuxine C, K36 Cyclosativene, T28 Cyclosteroids, T50-51 Cyclotetradecane derivatives, T41 Cycloundecanes, T30 Cyperene, T27 Cyperolone, T19 ep/-a-cyperone, T19 Cyperones, T20 Cyperotundone, T27 Cypridina luciferin, Y20 Cysteine, A4 Cystine, A4 Cytidine, 2 -deoxy, C4 Cytisine, K21 Cytochalasins, Y27... 

RN 154361-50-9 MF CijHzzFNjO MW 359.35 CN 5 -Deoxy-5-fluoro-A -[(pentyloxy)carbonyl]cytidine... 

C27H42FN3O10 174667-24-4) see Capecitabine 5 -deoxy-5-fluoro-A-[(pentyloxy)carbonyl]cytidine 2, 3 -diacetate... 

By analogy with the conversion of uridine 1 into cytidines 6, the conventional amination of inosine 235a, guanosine 235b, or xanthosine 235c and their 2 -deoxy analogues to the adenosines 237 requires ... 

A-Acetyl-9-deoxy-9-fluoroneuraminic acid (591) was prepared by treatment of a protected 6-hydroxyl precursor with A, A-diethylaminosulfur trifluoride (DAST) or through condensation of 2-acetamido-2,6-dideoxy-6-fluoro-D-mannopyranose with potassium di(/ >r/-butyl) oxaloacetate. Compound 591 is a substrate for cytidine monophosphate (CMP)-sialic acid synthetase, giving rise to CMP-5-A-acetyl-9-deoxy-9-fluoroneuraminic acid, which is cytotoxic against tumor cells. 5-A-Acetyl-3-fluoroneuraminic acids 592-594 were prepared through fluorine (or acetyl hypofluorite) addition (in AcOH) to methyl 5-acetamido-4,7,8,9-tetra-0-acetyI-2,6-anhy-dro-2,3,5-trideoxy-D- /ycm>D- a/arto-non-2-enopyranosate. Compound 592 was found to be a potent neuraminidase inhibitor. 

The susceptibilities of some of these fluorinated purine nucleosides to the action of enzymes are now described. In contrast to the inertness of the 2 -deoxy-2 -fluoro- and 3 -deoxy-3 -fluorocytidine analogs 739, 744, and 821 towards cytidine deaminase, the adenosine compounds 867, 883, and 906 are readily deaminated - by the adenosine deaminase in erythrocytes and calf intestine, but the resulting (deaminated) inosine compounds (from 867 and 883), as well as 888, are highly resistant - to cleavage by purine nucleoside phosphorylase (to give hypoxanthine base for the first two). The reason was discussed. Both 867 and 883 can form the 5 -triphosphates, without deamination, in human erythrocytes or murine sarcoma cells in the presence of 2 -deoxycoformycin, an adenosine deaminase inhibitor, but... 

Complete confirmation of the structures assigned to the ribonucleosides has been provided by a study of their 5-0- p -tolylsulfonyl derivatives. Whereas 2,3-O-isopropylideneuridine and 2,3-O-isopropylideneinosine give 5-p-tolylsulfonyl derivatives which, with sodium iodide, are converted to 5-deoxy-5-iodo compounds,30 31 the corresponding adenosine and cytidine... 

In contrast to uridine,389 cytidine does not yield a 5 -chloro-5 -deoxy derivative on reaction with N,N-dimethyl(chlorometh-animinium) chloride instead 2,2 -anhydrocytidine is formed.395 However, thionyl chloride or bromide in hexamethylphosphor-amide at room temperature achieves this selective replacement of the primary hydroxyl group of halogen in cytidine, and also in adenosine, in respective yields of 80 and 75% for the chloro compounds, and 55 and 30% for the bromo analogs.396... 

Figure 9.4 Monoterpene biosynthesis in peppermint oil gland secretory cells. The enzymes involved in this pathway are (1) 1-deoxy-D-xylulose 5-phosphate synthase, (2) 2-C-methyl-D-erythritol 4-phosphate reductoisomerase, (3) 2-C-methyl-D-erythritol 4-phosphate cytidyltransferase, (4) 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol kinase, (5) 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, (6) isopentenyl diphosphate isomerase, (7) geranyl diphosphate synthase, (8)...

Several of the oxo forms of the pyrimidines are particularly important in biological systems, and are normally referred to by their nonsystematic names such as cytosine [4-aminopyrimidin-2(l//)-one] 5, uracil [2,4(1//,3//)-pyrimidinedione] 6, and thymine (5-methyluracil) 7. Their nucleoside derivatives are also normally referred to by their nonsytematic names such as cytidine (l-/3-D-ribofuranosylcytosine) 8 and thymidine [l-(2-deoxy-/3-D-ribofur-anosyl)-5-methyluracil] 9. 

Selective chlorination or bromination of the 5 -hydroxyl group in unprotected D-ribonucleosides has been achieved75 by treatment with thionyl chloride or thionyl bromide, respectively, in hexamethyl-phosphoric triamide at room temperature for 10-15 hours the 5 -deoxy-5 -halogeno derivatives of cytidine and adenosine have been prepared in this way. The reactions presumably occur by way of alkoxyphosphonium salts as intermediates.78... 

The esters of cytidine 5 -pyrophosphate with 6-deoxy-a-D-xylo-hexopyranos-4-ulose (15) and 3,6-dideoxy-a-D-ert/f/iro-hexopyranos-4-ulose (16) are probably normal metabolites in Gram-negative bac-... 

A similar ester was prepared from cytidine 5 -triphosphate and 3-deoxy-D-manno-octulosonic acid by use of an enzyme188 from Escherichia coli, but its purification failed because of the extreme lability of this derivative. 

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