Literature DB >> 31588837

Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs.

Jong Hyun Cho1, Leda C Bassit2, Franck Amblard2, Raymond F Schinazi2.   

Abstract

Novel 7-trifluoromethyl-7-deazapurine ribonucleoside analogs (13a-c) and their Protides (15a-c) were successfully synthesized from ribolactol or 1-α-bromo-ribose derivatives using Silyl-Hilbert-Johnson or nucleobase-anion substitution reactions followed by key aromatic trifluoromethyl substitution. Newly prepared compounds were evaluated against a panel of RNA viruses, including HCV, Ebola or Zika viruses.

Entities:  

Keywords:  7-trifluoromethyl-7-deazapurine ribonucleoside; RNA viruses; Silyl-Hilbert-Johnson; protides

Mesh:

Substances:

Year:  2019        PMID: 31588837      PMCID: PMC7668401          DOI: 10.1080/15257770.2019.1674333

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN: 1525-7770            Impact factor:   1.381


  45 in total

1.  Aromatic trifluoromethylation with metal complexes.

Authors:  Olesya A Tomashenko; Vladimir V Grushin
Journal:  Chem Rev       Date:  2011-04-01       Impact factor: 60.622

Review 2.  Approved Antiviral Drugs over the Past 50 Years.

Authors:  Erik De Clercq; Guangdi Li
Journal:  Clin Microbiol Rev       Date:  2016-07       Impact factor: 26.132

3.  Synthesis and significant cytostatic activity of 7-hetaryl-7-deazaadenosines.

Authors:  Aurelie Bourderioux; Petr Naus; Pavla Perlíková; Radek Pohl; Iva Pichová; Ivan Votruba; Petr Dzubák; Petr Konecný; Marián Hajdúch; Kirsten M Stray; Ting Wang; Adrian S Ray; Joy Y Feng; Gabriel Birkus; Tomas Cihlar; Michal Hocek
Journal:  J Med Chem       Date:  2011-07-11       Impact factor: 7.446

4.  Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines.

Authors:  J S Pudlo; M R Nassiri; E R Kern; L L Wotring; J C Drach; L B Townsend
Journal:  J Med Chem       Date:  1990-07       Impact factor: 7.446

5.  6-(Het)aryl-7-deazapurine ribonucleosides as novel potent cytostatic agents.

Authors:  Petr Naus; Radek Pohl; Ivan Votruba; Petr Dzubák; Marián Hajdúch; Ria Ameral; Gabriel Birkus; Ting Wang; Adrian S Ray; Richard Mackman; Tomas Cihlar; Michal Hocek
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

6.  An efficient synthesis of 7-functionalized 7-deazapurine beta-D- Or beta-L-ribonucleosides: glycosylation of pyrrolo[2,3-D]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-Or L-ribofuranose.

Authors:  Xiaohua Peng; Frank Seela
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2007       Impact factor: 1.381

Review 7.  Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases.

Authors:  Lars Petter Jordheim; David Durantel; Fabien Zoulim; Charles Dumontet
Journal:  Nat Rev Drug Discov       Date:  2013-06       Impact factor: 84.694

8.  Synthesis and Evaluation of 2,6-Modified Purine 2'-C-Methyl Ribonucleosides as Inhibitors of HCV Replication.

Authors:  Longhu Zhou; Hongwang Zhang; Sijia Tao; Maryam Ehteshami; Jong Hyun Cho; Tamara R McBrayer; Philip Tharnish; Tony Whitaker; Franck Amblard; Steven J Coats; Raymond F Schinazi
Journal:  ACS Med Chem Lett       Date:  2015-11-23       Impact factor: 4.345

9.  Synthesis and biological activity of 5-fluorotubercidin.

Authors:  Xiaojing Wang; Punit P Seth; Ray Ranken; Eric E Swayze; Michael T Migawa
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2004       Impact factor: 1.381

10.  Synthesis and antiviral activity of 7-deazaneplanocin A against orthopoxviruses (vaccinia and cowpox virus).

Authors:  Balakumar Arumugham; Hyo-Joong Kim; Mark N Prichard; Earl R Kern; Chung K Chu
Journal:  Bioorg Med Chem Lett       Date:  2005-11-03       Impact factor: 2.940

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