Cytidine 5-deoxy-5-fluoro

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... 

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... 

Condensation of LXVIa (R = p-toluyl) with monomercurithymine (prepared from 1-acetylthymine) produces a mixture of acylated nucleoside anomers (LXVlb and LXVIc, R = thyminyl) which are separated and de-esterified to thymidine and a-thymidine. Similarly, reaction of N-acetylcytosinemercury (LV) with LXVIa (R = p-chlorobenzoyl) yields the a and ft anomers of acylated 2-deoxycytidine which, after separation and deacylation, are converted smoothly to 2-deoxycytidine (LXVlb, R = H, R = cytosinyl) and its a anomer (LXVIc). In like manner, 2-deoxy-5 -fluoro-uridine and -cytidine were synthesized, along with their... 

Deoxy-5-fluoro-N4-((n-pentyloxy)carbonyl)cytidine may be prepared according to US Patent No. 6,114,520. 

From 2, 3 -bis-0-(tert-butyldimethylsilyl)-5 -deoxy-5-fluorocytidine and n-pentylchloroformate in dichloromethane and pyridine may be obtained 2, 3 -bis-0-(tert-butyldimethylsilyl)-5 -deoxy-5-fluoro-N4-((pentyloxy)carbonyl) cytidine.From 2, 3 -bis-0-(tert-butyldimethylsilyl)-5 -deoxy-5-fluoro-N4-((pentyloxy)carbonyl)cytidineand tetrabutylammonium fluoride in tetrahydrofuran at room temperature for 2 hours may be prepared the product which by hydrolyses may be converted to 5-deoxy-5-fluoro-N4-((pentyloxy)carbonyl)cytidine. Purification of the product may be carried out by silica gel chromatography (using dichloromethane methanol = 20 1 as an eluent). 

Metabolic pathway of capecitabine to 5-FU. 5-DFCR = 5 -deoxy-5-fluoro-cytidine 5-DFUR = 5 -deoxy-5-fluorouridine... 

Figure 4 Catalytic activation of cytosine for C5-methylation by nucleophilic addition of a thiolate at the C6 position, (a) The chemical mechanism of enzymatic DNA cytosine-S methylation. Mechanism-based inhibition of DMA MTases by cytidine analogs 5-fluoro-2 -deoxycytidine (b), 5-aza-2 -deoxy-cytidine (c), and 2-pyrimidinone-l-p-D-(2 -deoxyriboside) (d).

Deoxy-6-fluoromannose, D-104 2 -Deoxy-2 -(fluoromethylene)cytidine, T-48 9-(3-Deoxy-3-fluoro-p-D-ribofuranosyl)guanine, D-94 2-Deoxy-2-fluororibopyranosyl fluoride, D-105 2-Deoxy-2-fluororibose, D-106... 

In their initial work, these authors reported a poten-tiometric study on the ability of the Zn " " complex of cyclen (80) to interact with the deoxyribonucleotides 2 -deoxyadenosine (dA), 2 -deoxyguanosine (dG), 2 -deoxy-cytidine (dC), 2 -deoxythymidine (dT), uridine (U), and 3 -azido-3 - deoxythymidine (AZT). [Zn(80)] " had a good selectivity for dT, U, AZT, and the related derivatives Ff (ftorafur, 5-fluoro-l-(tetrahydro-2-furyl)uracil), and... 

Reaction of e. coli ribonucleotide reductase with ( )-2 -fluoro-methylene-2 -deoxy-cytidine 5 -diphosphate... 

Deoxy-5-fluoro-A4-(3,4,5-trimethoxybenzoyl)cytidine has been prepared as a prodrug of the antitumour agent 5 -deoxy-5-fluorouridine, and its stability and degradation were examined at... 

Azido and 3 -amino analogues of 2 -deoxy-5-substituted uridine and cytidine, together with 3 -amino-5 -fluoro-thymidine, have been prepared by standard procedures using 3 -0-mesyl ester intermediates the most active anti-cancer compounds were the 3 -amino-5-fluoro analogues of 2 -deoxyuridine and 2 -deoxycytidine cuid the 3 -amino analogue of 2 -deoxycytidine.An alternative doubleinversion sequence at C-3 using a 3 -chloro-3 -deoxyxylo-nucleo-side intermediate has been described for the preparation of 3 -... 

C2oH 8N7Na02iP, Sodium guanylyl-3, 5 -cytidine hydrate, 39B, 899 C21H31FN2O11S, 2,3,4,5-Tetraacetyl-1-deoxy-1-ethylthio-1-(5-fluoro-uracil-1-yl)-D-arabinose aldehydrol ethanol solvate, 43B, 580 C22H32N3O13, Cytidine N-carbobenzoxyglutamic acid (1 1) dihydrate, 41B, 519... 

D-lyxopyranosyl nucleosides with hydrogen halides to give the 3 -bromo- or 3 -chloro-3 -deoxy-nucleosides (406), or a mixture of the 2 - and 3 -fluoro-deoxy-nucleosides (407). 9-(3-Deoxy-3-iodo-)3-D-xylofuranosyl)hypoxanthine has been synthesized and converted into 3 -amino-3 -deoxy- and 3, 4 -unsatu-rated nucleosides as shown in Scheme 138. Both l-(2-deoxy-2-fluoro- and 2-chloro-2-deoxy-j8-D-arabinofuranosyl)cytidine have been prepared from the corresponding halogeno-sugar derivatives by standard methods (see Schemes 43 and 46). ... 

Cytidine has been converted into l-(5-amino-5-deoxy-j8-D-arabinofuranosyl) cytosine by a sequence of reactions involving A-benzoylation, sulphonation, acetylation, displacement with azide ion, e/c., and l-(3-amino-3-deoxy-jS-D-arabinofuranosyl)-6-azauracil was derived from 2, 3 -di-0-methanesulphonyl-5 -O-trityl-6-azauridine via 2,2 - and 2, 3 -anhydro-nucleosides. Other syntheses have been accomplished by the condensation of an appropriately derivatized amino-sugar with either a pyrimidine or purine derivative for example, the Hilbert route was used to prepare l-(2-amino-2-deoxy-a-D-arabino- and -jS-o-xylo-furanosyl)cytosine. > The reactivity of l,3,4,6-tetra-0-acetyl-2-acyl-amido-2-deoxy-j3-D-glucopyranoses in condensation reactions with 2,6-dichloro-purine, theophylline, and 6-benzylaminopurine was shown to be in the order benzamido > acetamido > phthalimido. 9-(3-Acetamido-2,5-di-0-acetyl-3-deoxy-j8-D-ribofuranosyl)-2,6-dichloropurine has been synthesized and converted into the corresponding 2,6-diamino- and 6-amino-2-chloro(fluoro)-nucleosides. ... 

Jhansi RaniV, RaghavendraA, Kishore P, Nanda KumarY, Hema Kumar K, Jagadeeswarareddy K (2012) Synthesis and biological activity evaluation of cytidine-5 -deoxy-5-fluoro-N-[(alkoxy/aryloxy)] carbonyl-cycUc 2, 3 -carbonates. Eur J Med Chem 54 690-696... 

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