Literature DB >> 17900141

Improved chemical syntheses of 5,6-dihydro-5-fluorouracil.

Andrew L LaFrate1, John A Katzenellenbogen.   

Abstract

5,6-dihydro-5-fluorouracil (5-DHFU) is a metabolite of the chemotherapy drug 5-fluorouracil (5-FU) of importance for biological studies. 5-DHFU has been prepared by enzymatic reduction of 5-FU and in very low yield by hydrogenation of 5-FU; however, a practical chemical synthesis is not available. Facile racemic syntheses of 5-DHFU from 5-FU or uracil, using p-methoxybenzyl protecting groups followed by L-Selectride reduction, are reported.

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Year:  2007        PMID： 17900141      PMCID： PMC2562335          DOI： 10.1021/jo071255z

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Iridium-catalyzed asymmetric hydrogenation of fluorinated olefins using N,P-ligands: a struggle with hydrogenolysis and selectivity.

Authors:  Mattias Engman; Jarle S Diesen; Alexander Paptchikhine; Pher G Andersson
Journal:  J Am Chem Soc       Date:  2007-03-22       Impact factor: 15.419

2.  Benzhydryl as an efficient selective nitrogen protecting group for uracils.

Authors:  Fan Wu; Musole G Buhendwa; Donald F Weaver
Journal:  J Org Chem       Date:  2004-12-24       Impact factor: 4.354

3.  Stereoselective total syntheses and reassignment of stereochemistry of the freshwater cyanobacterial hepatotoxins cylindrospermopsin and 7-epicylindrospermopsin.

Authors:  Geoffrey R Heintzelman; Wen-Kui Fang; Stephen P Keen; Grier A Wallace; Steven M Weinreb
Journal:  J Am Chem Soc       Date:  2002-04-17       Impact factor: 15.419

4.  Lack of contribution of dihydrofluorouracil and alpha-fluoro-beta-alanine to the cytotoxicity of 5'-deoxy-5-fluorouridine on human keratinocytes.

Authors:  Jean-Louis Fischel; Patricia Formento; Joseph Ciccolini; Marie-Christine Etienne-Grimaldi; G Milano
Journal:  Anticancer Drugs       Date:  2004-11       Impact factor: 2.248

5.  Severe 5-fluorouracil toxicity associated with a marked alteration of pharmacokinetics of 5-fluorouracil and its catabolite 5-fluoro-5,6-dihydrouracil: a case report.

Authors:  G Bocci; R Danesi; G Allegrini; F Innocenti; A Di Paolo; A Falcone; P F Conte; M Del Tacca
Journal:  Eur J Clin Pharmacol       Date:  2002-12       Impact factor: 2.953

Review 6.  Pyrimidine degradation defects and severe 5-fluorouracil toxicity.

Authors:  A B P van Kuilenburg; R Meinsma; A H van Gennip
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2004-10       Impact factor: 1.381

Review 7.  5-fluorouracil: mechanisms of action and clinical strategies.

Authors:  Daniel B Longley; D Paul Harkin; Patrick G Johnston
Journal:  Nat Rev Cancer       Date:  2003-05       Impact factor: 60.716

8.  (R)-5-fluoro-5,6-dihydrouracil: kinetics of oxidation by dihydropyrimidine dehydrogenase and hydrolysis by dihydropyrimidine aminohydrolase.

Authors:  D J Porter; J A Harrington; M R Almond; G T Lowen; T Spector
Journal:  Biochem Pharmacol       Date:  1994-08-17       Impact factor: 5.858
  8 in total
  2 in total

Review 1.  Dihydrofolate reductase, thymidylate synthase, and serine hydroxy methyltransferase: successful targets against some infectious diseases.

Authors:  Hina Shamshad; Rowaida Bakri; Agha Zeeshan Mirza
Journal:  Mol Biol Rep       Date:  2022-03-07       Impact factor: 2.742

2.  Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation.

Authors:  Yi-Yun Yu; Gunda I Georg
Journal:  Chem Commun (Camb)       Date:  2013-03-25       Impact factor: 6.222
  2 in total

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