Literature DB >> 22773864

Bromination at C-5 of Pyrimidine and C-8 of Purine Nucleosides with 1,3-Dibromo-5,5-dimethylhydantoin.

Ramanjaneyulu Rayala1, Stanislaw F Wnuk.   

Abstract

Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5- dimethylhydantoin in aprotic solvents such as CH(2)Cl(2), CH(3)CN, 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 efficiency of bromination.

Entities:  

Year:  2012        PMID： 22773864      PMCID： PMC3389796          DOI： 10.1016/j.tetlet.2012.04.081

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  9 in total

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Journal:  J Med Chem       Date:  1985-10       Impact factor: 7.446

7.  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.

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Journal:  J Med Chem       Date:  1985-09       Impact factor: 7.446

8.  Synthesis and tumor uptake of 5-82Br- and 5-131I-labeled 5-halo-1-(2-fluoro-2-deoxy-beta-D-ribofuranosyl)uracils.

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Journal:  J Med Chem       Date:  1989-06       Impact factor: 7.446

9.  Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.

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  9 in total
  5 in total

1.  Studies toward the oxidative and reductive activation of C-S bonds in 2'-S-aryl-2'-thiouridine derivatives.

Authors:  Ramanjaneyulu Rayala; Alain Giuglio-Tonolo; Julie Broggi; Thierry Terme; Patrice Vanelle; Patricia Theard; Maurice Médebielle; Stanislaw F Wnuk
Journal:  Tetrahedron       Date:  2016-04-21       Impact factor: 2.457

2.  Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.

Authors:  Jessica Zayas; Marie Annoual; Jayanta Kumar Das; Quentin Felty; Walter G Gonzalez; Jaroslava Miksovska; Nima Sharifai; Akira Chiba; Stanislaw F Wnuk
Journal:  Bioconjug Chem       Date:  2015-07-02       Impact factor: 4.774

3.  Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization.

Authors:  Sam Kavoosi; Ramanjaneyulu Rayala; Brenna Walsh; Maria Barrios; Walter G Gonzalez; Jaroslava Miksovska; Logesh Mathivathanan; Raphael G Raptis; Stanislaw F Wnuk
Journal:  Tetrahedron Lett       Date:  2016-08-19       Impact factor: 2.415

4.  Salvadenosine, a 5'-deoxy-5'-(methylthio) nucleoside from the Bahamian tunicate Didemnum sp.

Authors:  Matthew T Jamison; Christopher N Boddy; Tadeusz F Molinski
Journal:  J Org Chem       Date:  2014-10-20       Impact factor: 4.354

5.  Palladium-catalyzed direct arylation of 5-halouracils and 5-halouracil nucleosides with arenes and heteroarenes promoted by TBAF.

Authors:  Yong Liang; Jennifer Gloudeman; Stanislaw F Wnuk
Journal:  J Org Chem       Date:  2014-04-23       Impact factor: 4.354
  5 in total

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