- A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues
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A general and efficient approach was developed for the introduction of S-functionality at the C-5 position of cytosine and uracil nucleosides and their analogues. The key step is a palladium-catalyzed C-S coupling of the corresponding 5-bromo nucleoside derivative and alkyl thiol. The butyl 3-mercaptopropionate coupling products were further converted to the corresponding disulphides, the stable precursors of 5-mercaptopyrimidine nucleosides. the Partner Organisations 2014.
- Kananovich, Dzmitry G.,Reino, Alli,Ilmarinen, Kaja,Roomusoks, Marko,Karelson, Mati,Lopp, Margus
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p. 5634 - 5644
(2014/07/22)
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- An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI)
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An efficient and facile strategy has been developed for bromination of nucleosides using sodium monobromoisocyanurate (SMBI). Our methodology demonstrates bromination at the C-5 position of pyrimidine nucleosides and the C-8 position of purine nucleosides. Unprotected and also several protected nucleosides were brominated in moderate to high yields following this procedure.
- Maity, Jyotirmoy,Stromberg, Roger
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p. 12740 - 12750
(2013/11/06)
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- Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin
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Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5-dimethylhydantoin in aprotic solvents such as CH 2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination.
- Rayala, Ramanjaneyulu,Wnuk, Stanislaw F.
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experimental part
p. 3333 - 3336
(2012/07/30)
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- Highly efficient method for C-5 halogenation of pyrimidine-based nucleosides in ionic liquids
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A novel, highly efficient, convenient, and benign methodology for C-5 halogenation of pyrimidine-based nucleosides has been developed using N-halosuccinimides as halogenating reagents without using any catalyst in ionic liquid medium. The ionic liquids were successfully recovered and reused for all the reactions. Georg Thieme Verlag Stuttgart.
- Kumar, Vineet,Yap, Jeremy,Muroyama, Andrew,Malhotra, Sanjay V.
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experimental part
p. 3957 - 3962
(2010/03/26)
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- CYTIDINE ANALOGS AND METHODS OF USE
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Cytidine analogs, their prodrugs and/or metabolites are employed as pharmaceutically active compounds for treatment of diseases responsive to such compounds. Particularly preferred diseases include viral diseases (e.g., HCV infection) and neoplasms.
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Page/Page column 21
(2010/02/08)
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- Photoinduced energy transfer in associated but noncovalently linked photosynthetic model systems
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The synthesis and photophysical characterization of nucleobase-substituted porphyrins designed to form rigid hydrogen-bonded ensembles, and to allow for energy transfer within the resulting complexes, is reported. Watson-Crick nucleobase-pairing interacti
- Sessler, Jonathan L.,Wang, Bing,Harriman, Anthony
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p. 704 - 714
(2007/10/02)
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- Mechanisms of Bromination of Uracil Derivatives. 6. Cytosine and N-Substituted Derivatives
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The reactions of bromine with cytosine, 1-methylcytosine, cytidine, and 3-methylcytosine in acidic aqueous sloutions have been studied.Initially adducts (5-bromo-5,6-dihydro-6-hydroxycytosines) are produced which are clearly observable by proton NMR, albeit in their protonated forms in the acidic media used.In time the adducts undergo elimination of water to give substitution products, 5-bromocytosines.Kinetic measurements of the initial reaction in the pH range 0-5 are consistent with the adducts resulting from rate-determining attack of bromine in the free base form of the cytosine substrates followed by capture of the cation so produced by water.An alternative mechanism involving first hydration and then bromine attack can be ruled out.
- Tee, Oswald S.,Kornblatt, Mary Judith,Berks, Charles G.
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p. 1018 - 1023
(2007/10/02)
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