69304-47-8Relevant articles and documents
Syntheses of 5-(2-radiohaloethyl)- and 5-(2-radiohalovinyl)-2′-deoxyuridines. Novel types of radiotracer for monitoring cancer gene therapy with PET
Yu, Chung-Shan,Eisenbarth, Joseph,Runz, Armin,Weber, Klaus,Zeisler, Stephan,Oberdorfer, Franz
, p. 421 - 439 (2003)
Syntheses of 5-(2-[18F]fluoroethyl)- (1) 5-(2-[80Br] bromoethyl), (2), undeprotected (E)-5-(2-[18F]fluorovinyl)- (3) and (E)-5-(2-[80Br]bromovinyl),2′-deoxyuridines (4) as the tracers for monitoring cancer gene therapy with positron emission tomography were described. Decay corrected radiochemical yield and synthesis time including labeling and HPLC purification from end of bombardment for 1 was 9.5% and 2 hours, respectively; yield and time for 2 was 16% and 2 hours, respectively. Chemical (approximate to radiochemical) yield and time for synthesis of 3 was 7.5% and 7 minutes, respectively. Radiochemical yield and synthesis time including labeling and HPLC purification of an analytical sample of 4 was 60% and 30 minutes, respectively. Both 2 and 4 received the side reactions during HPLC purification, i.e. ring closure and cleavage of glycosidic bond, respectively. Application of 2 and 4 needed to be confirmed by in vitro or in vivo experiments. Radiochemical yield of 1 could be optimized by employing a modified protocol for preparation of its precursor. The preparation of fluorovinyl counterparts had demonstrated the potential utility of the stannane, 3-tolyl-3′,5′-di-O-acetyl-(E)-5-(2-stannylvinyl)- 2′-deoxyuridine 7. Copyright
Novel synthesis process of bromovudine and bromovudine
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, (2021/08/11)
The invention discloses a novel synthesis process of bromovudine and bromovudine, which comprises the following steps: taking beta-thymidine as an initial raw material, carrying out a formylation reaction on beta-thymidine and DMF-DMA to generate an intermediate I, heating the intermediate I and acetic acid to form a ring to generate an intermediate II, and reacting the intermediate II with hydrobromic acid to obtain the bromovudine. The novel synthesis process of bromovudine comprises the following steps: firstly, carrying out formylation reaction on beta-thymidine and DMF-DMA, then heating with acetic acid to form a ring, and finally, carrying out ring opening reaction with hydrobromic acid to obtain the bromovudine. The beta-thymidine is used as the starting material, the starting material is low in price and easy to obtain, expensive palladium does not need to be used as a catalyst, and the raw material cost of bromovudine can be effectively reduced. The synthetic route of the bromovudine is short, the conditions are mild, the operation is convenient, and the method is suitable for industrial production.
A comparison between immobilized pyrimidine nucleoside phosphorylase from Bacillus subtilis and thymidine phosphorylase from Escherichia coli in the synthesis of 5-substituted pyrimidine 2′-deoxyribonucleosides
Serra, Immacolata,Bavaro, Teodora,Cecchini, Davide A.,Daly, Simona,Albertini, Alessandra M.,Terreni, Marco,Ubiali, Daniela
, p. 16 - 22 (2013/10/22)
Pyrimidine nucleoside phosphorylase from Bacillus subtilis (BsPyNP, E.C. 2.4.2.3) and thymidine phosphorylase from Escherichia coli (EcTP, E.C. 2.4.2.4) were used, as immobilized enzymes, in the synthesis of 5-halogenated pyrimidine 2′-deoxyribonucleosides (14-18) by transglycosylation in fully aqueous medium. From the comparative study of the two biocatalysts, no remarkable differences emerged about their substrate specificity, bioconversion yield, stability in organic cosolvents (DMF and MeCN). Moreover, both biocatalysts could be recycled for at least 5 times with no loss of the productivity. Both enzymes do not accept arabinonucleosides and 2′,3′- dideoxynucleosides as substrates, whereas they catalyze bioconversions involving 5′-deoxyribonucleosides and 5-halogenated uracils. The synthesis of compounds 14-18 proceeded at a similar conversion (33-68% for BsPyNP and 25-62% for EcTP, respectively). Immobilization was found to exert, for both the biocatalysts, a dramatic enhancement of stability upon incubation in MeCN. Optimization of 5-fluoro-2′-deoxyuridine (14) synthesis (pH 7.5, 10 mM phosphate buffer, nucleoside/nucleobase 3:1 molar ratio) and subsequent scale-up afforded the target compound in 73% (EcTP) or 76% (BsPyNP) conversion (about 9 g/L).
