38645-23-7Relevant academic research and scientific papers
Selective oxidation of uracil and adenine derivatives by the catalytic system MeReO3/H2O2 and MeReO3/urea hydrogen peroxide
Saladino, Raffaele,Carlucci, Paola,Danti, Maria Chiara,Crestini, Claudia,Mincione, Enrico
, p. 10031 - 10037 (2007/10/03)
Methyltrioxorhenium (MTO) is a useful and selective catalyst for the oxidation of uracil and purine derivatives using environmentally friendly hydrogen peroxide (H2O2, 30% water solution) or hydrogen peroxide/urea adduct (UHP) as oxygen atom donors. In particular, the MTO/UHP system constitutes a convenient combination to convert uracil derivatives into the biologically relevant 5,6-oxiranyl-5,6-dihydrouracils in good yields. Purine derivatives are selectively oxidized to the corresponding 1-oxides, the best yield being obtained in the presence of pyrazine-2-carboxylic acid (PCA). The oxidation of the plasmid pBG1 is also reported as the first example of double-strand DNA cleavage mediated by the catalytic system MTO/H2O2. (C) 2000 Elsevier Science Ltd.
Oxidation of 1,3-dimethylthymine and 1,3-dimethyluracil with oxone in the solid to solid state
Hong, Yongrae,Chang, Soonjae,Hahn, Bosup,Toda, Fumio
, p. 1455 - 1459 (2007/10/03)
The oxidation of the title substrates with Oxone in the presence of camphor in the solid to solid state afforded a simple and efficient method for epoxidation under mild reaction condition.
Oxidation of 1,3-dimethylthymine with oxone catalyzed by 5,10,15,20-tetrakis (4N-methylpyridiniumyl)porphyrinatomanganese (III) pentaacetate
Chauhan,Gupta, Mamta,Gulati,Nizar
, p. 1267 - 1270 (2007/10/03)
The reaction of 1,3-dimethylthymine 2 with KHSO5 (oxone) catalyzed by 5, 10, 15, 20-tetrakis-(4N-methylpyridiniumyl)porphyrinatomanganese (III) pentaacetate 1 [T4MPyPMn (III) (OAc)5] in phosphate buffer gives 1,3-dimethyl-5-hydroxymethyluracil 3, 1,3-dimethyl-5-formyluracil 4, 1,3-dimethyluracil-5-carboxylic acid 5, cis-1,3-dimethylthymine-5,6-glycol 6 and 1,3,5-trimethyl-5-hydroxybarbituric acid 8 in different yields depending on the pH of the reaction medium. Oxidation of the 5-methyl group of 1,3-dimethylthymine to 1,3-dimethyl-5-hydroxymethyluracil 3, 1,3-dimethyl-5-formyluracil 4 and the corresponding acid 5 with oxone catalyzed by T4MPyPMn (III) (OAc)5 may be explained by hydrogen abstraction and recombination mechanism, whereas oxidation of 5,6-double bond of thymine to cis-1,3-dimethylthymine-5,6-glycol 6 and 1,3,5-trimethyl-5-hydroxybarbituric acid 8 may be explained either by electron transfer followed by oxygen atom transfer or by the involvement of hydroxy radicals.
Studies on the chemistry of pyrimidine derivatives with dimethyldioxirane: Synthesis, cytotoxic effect and antiviral activity of new 5,6-oxiranyl-5,6-dihydro and 5-hydroxy-5,6-dihydro-6-substituted uracil derivatives and pyrimidine nucleosides
Saladino, Raffaele,Bernini, Roberta,Crestini, Claudia,Mincione, Enrico,Bergamini, Alberto,Marini, Stefano,Palamara, Anna Teresa
, p. 7561 - 7578 (2007/10/02)
The oxidation of uracil derivatives and pyrimidine nucleosides performed in CH2Cl2 with dimethyldioxirane afforded new 5,6-oxiranyl-5,6-dihydro and cis-/trans-5,6-dihvdroxv-5,6-dihydro-derivatives. When the oxidations were performed in the presence of methanol as nucleophile cis- and trans- 5-hydroxy-6-methoxy-5,6-dihydro derivatives were obtained in acceptable yields. Cis- and trans-1,3- dimethyl-5-hydroxy-6-alkylamino-5,6-dihydro uracils were obtained by nucleophilic ring opening of the 1,3-dimethyl-5,6-oxiranyl-5,6-dihydro uracil in the purified form. Interestingly some of the new title products revealed low cytotoxicity and selective antiviral activity against DNA and RNA Viruses. In particular, compound 17b shows a strong and selective inhibition of the Sendai virus with lower effect on Herpes Simplex-1 virus. Compound 17b is also able to slightly inhibit HIV-1 virus at high concentrations, but in this case a cytotoxic effect was observed.
Oxidation of uracil derivatives and pyrimidine nucleosides by dimethyldioxirane: A new and mild synthesis of 5,6-oxiranyl-5,6-dihydro and 5,6-dihydroxy-5,6-dihydro-derivatives
Lupattelli, Paolo,Saladino, Raffaele,Mincione, Enrico
, p. 6313 - 6316 (2007/10/02)
The oxidation of title substrates with dimethyldioxirane afforded 5,6-oxiranyl-5,6-dihydro and cis- / trans-5,6-disubstituted-5,6-dihydro-derivatives.
Oxidation of Thymines by Peroxosulfate Ions in Water
Itahara, Toshio,Fujii, Yukiko,Tada, Miki
, p. 3421 - 3424 (2007/10/02)
Oxidation of thymines by sodium peroxodisulfate in water at 85 deg C gave the corresponding 5-(hydroxymethyl)uracils and 5-formyluracils.The reaction may proceed via thymine cation radicals.On the other hand, oxidation of thymines by potassium peroxomonosulfate in water gave the corresponding cis-5,6-dihydroxy-5,6-dihydrothymines and 5-hydroxy-5-methylbarbituric acids.Furthermore, treatment of thymine with both potassium peroxomonosulfate and hydrogen peroxide in water gave cis-6-hydroperoxy-5-hydroxy-5,6-dihydrothymine.
OXIDATION OF 1,3-DIMETHYL DERIVATIVES OF PYRIMIDINE BASES WITH m-CHLOROPERBENZOIC ACID
Harayama, Takashi,Kotoji, Kayoko,Yoneda, Fumio,Taga, Tooru,Osaki, Kenji,Nagamatsu, Tomohisa
, p. 2056 - 2058 (2007/10/02)
Oxidation of 1,3-dimethylthymine (1), 1,3-dimethyluracil (2), and 5-fluoro-1,3-dimethyluracil (3) with m-chloroperbenzoic acid were investigated. 1 gave the cis diol 5,6-dihydrothymine derivative (4) stereoselectively.Its stereostructure was definitely determined by an X-ray analysis. 2 afforded 7, 8, and 9, and 3 afforded 8.KEYWORDS - m-chloroperbenzoic acid oxidation; 1,3-dimethylthymine; 1,3-dimethyluracil; 5-fluoro-1,3-dimethyluracil; cis 5,6-dihydroxy-5,6-dihydrothymine
