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5- Trifluoromethyl- 2 -deoxyuridine

Trifluridine, C2qH22F2N20, (5-trifluoromethyl-2 -deoxyuridine [70-00-8] F TdU, 14) was first prepared (30) in 1962. It is used for topical therapy of herpes vims-infected eyes. It is especially usefiil for treating infections that are resistant to IdU therapy. Like IdU, trifluridine is incorporated into DNA in place of thymidine in both infected and uninfected cells. But it is 10 times more potent than IdU against herpes keratitis in rabbits and 10 times more soluble in water. Trifluridine is also usefiil in treating human cytomegalovims (HCMV), but its toxicity to bone marrow may limit its clinical use. [Pg.305]

Trifluoromethyl-2 -deoxyuridine, trifluridine (Viroptic ), is an anti-viral drug acting on TS via another mechanism. It is a mechanism-based inactivator of thy-midylate synthase (Figs. 27 and 28). Trifluridine is marketed for the topical treatment of Herpes simplex virus infection in eyes. [Pg.580]

Trifluridine (5-trifluoromethyl-2 -deoxyuridine) (Viroptic ) is marketed for the topical treatment of herpes simplex virus infection in the eyes. This antiviral drug is a mechanism-based inactivator of thymidylate synthase. The mechanism of inhibition and synthesis of trifluoridine are reported in Chapter 7. [Pg.284]

Trifluridine (5-trifluoromethyl-2 -deoxyuridine) is a fluorinated pyrimidine nucleoside with in vitro inhibitory activity against HSV types 1 and 2, CMV, vaccinia, and some adenoviruses. [Pg.825]

Nestler HJ and Garrett ER, Prediction of stability in pharmaceutical preparations XV, Kinetics of hydrolysis of 5-trifluoromethyl-2 -deoxyuridine, /. Pharm. Sci., 1117-1125 (1968). Cited in Ritschel. NB No further details reported. Also reported the following values (spectro unless noted) 5-trifluoromethyl-2 -deoxyuridine, 7.85 5-carboxy-2 -deoxyuridine, 4.0 and 9.8 5-trifluoromethyluracil, 7.4 and 12.6 (kinetic) 5-carboxyuracil, 4.20 and 9.10 5-carboxyuracil, 4.25 (potentio) and 8.90 (potentio) uracil, 9.0 and >13.0. [Pg.494]

Ritschel Nestler HJ and Garrett ER, Prediction of stability in pharmaceutical preparations XV, Kinetics of hydrolysis of 5-trifluoromethyl-2 -deoxyuridine, J. Pharm. Sci, 1117-1125 (1968). [Pg.636]

Trifluoromethyl-2 -deoxyuridine (C10H11F3N2O5) 5-Trifluoromethyluracil (C5H3F3N2O2) l-(3-Trifluoromethylphenyl)piperazine (C11H13F3N2)... [Pg.689]

Synonyms 2 -deoxy-5-(trifluoromethyl)uridine 5-(trifluoromethyl)-2 -deoxyuridine F3TDR Viroptic trifluorothymidine TFT Thilo ... [Pg.1238]

Heidelberger C, Parsons DG, Remy DC (1964) Syntheses of 5-trifluoromethyluracil and 5-trifluoromethyl-2 -deoxyuridine. J Med Chem 7 1-5... [Pg.572]

Wataya Y, Sonobe Y, Maeda M, Yamaizumi Z, Aida M, Santi DV (1987) Reaction of 5-trifluoromethyl-2 -deoxyuridine and l-methyl-5-trifluoromethyluracil with methoxy-amine model studies for the interaction between thymidylate synthetase and 5-trif luoromethyl-2 -deoxyutidine 5 -phosphate. J Chem Soc Perkin Trans 1 2141-2147... [Pg.572]

Takatori S, Matsuda A, Yamashita J-I, Hayatsu H, Wataya Y (1994) Rapid, stepwise substitution of fluorines in 5-trifluoromethyl-2 -deoxyuridine by bisidfite. Nucleos Nucleot 13 2105-2111... [Pg.572]

TakedaS, Yamashita J, SaitoH, UcMda J, SatakeH,YamadaY, UnemiN, WatayaY,Hayatsu H (1991) Antitumor activity of FTC-092, a masked 5-trifluoromethyl-2 -deoxyuridine derivative. Cancer Chemother Pharmacol 29 122-126... [Pg.662]

FLUORINECOMPOUNDS,ORGANIC - FLUORINATED AROMATIC COMPOUNDS] (Volll) 5-Trifluoromethyl-2y-deoxyuridine [70-00-8]... [Pg.1017]

This nucleoside 202 can be synthesized in a number of ways biological transformation using nucleic base transferase, trifluoromethylation of 2 -deoxyuridine or 2 -deoxy-5-halouridine, or a coupling reaction of silylated 5-triiluoromethylur-acil 203 and 2-deoxyribose derivative 204 " (see Scheme 12.47). In the last case, 5-trifluoromethyluracil 205 is an important intermediate for the preparation of 202. [Pg.449]

Target compound 202 is also provided by reacting a halogenated perfluor-oalkane (e.g., trifluoromethyl iodide) with a nucleic acid base (2 -deoxyuridine 216) in the presence of a sulfoxide, hydrogen peroxide, and an iron (11) salt (Scheme 12.48). [Pg.451]

Markley JC, Chirakul P, Sologub D, Sigurdsson ST (2001) Incorporation of 2 -deoxy-5-(trifluoromethyl)uridine and 5-cyano-2 -deoxyuridine into DNA. Bioorg Med Chem Lett 11 2453-2455... [Pg.572]

An alternative approach to 7 was based on direct trifluoromethylation of the corresponding deoxyuridine derivatives 32 or 84, using CFjCOOH-XeFj [108] and CF3I-CU-HMPA [109] as the reagents, respectively (Scheme 23). [Pg.600]

Dipple A, Heidelbetger C (1966) Fluorinated pyrimidines. XXVIII. The synthesis of 5-trifluoromethyl-6-azauracil and 5-trifluotomethyl-6-aza-2 -deoxyuridine. J Med Chem 9 715-718... [Pg.713]

See other pages where 5- Trifluoromethyl- 2 -deoxyuridine is mentioned: [Pg.52]    [Pg.272]    [Pg.448]    [Pg.306]    [Pg.246]    [Pg.363]    [Pg.312]    [Pg.272]    [Pg.52]    [Pg.84]    [Pg.349]    [Pg.272]    [Pg.121]    [Pg.448]    [Pg.450]    [Pg.306]    [Pg.246]    [Pg.363]    [Pg.312]    [Pg.600]    [Pg.131]    [Pg.537]    [Pg.272]   
See also in sourсe #XX -- [ Pg.123 ]



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