2. Academic Validation
  3. Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7-Deazapurine Ribonucleosides

Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7-Deazapurine Ribonucleosides

  • J Med Chem. 2017 Mar 23;60(6):2411-2424. doi: 10.1021/acs.jmedchem.6b01766.
Michal Tichý 1,  Sabina Smoleń 1,  Eva Tloušt'ová 1,  Radek Pohl 1,  Tomáš Oždian 2,  Klára Hejtmánková 2,  Barbora Lišková 2,  Soňa Gurská 2,  Petr Džubák 2,  Marián Hajdúch 2,  Michal Hocek 1 3
Affiliations

Affiliations

  • 1 Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Gilead Sciences & IOCB Research Center , Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
  • 2 Institute of Molecular and Translational Medicine, Palacky University and University Hospital in Olomouc, Faculty of Medicine and Dentistry , Hněvotínská 5, CZ-775 15 Olomouc, Czech Republic.
  • 3 Department of Organic Chemistry, Faculty of Science, Charles University in Prague , Hlavova 8, CZ-12843 Prague 2, Czech Republic.
PMID: 28221790 DOI: 10.1021/acs.jmedchem.6b01766
Abstract

Two isomeric series of new thieno-fused 7-deazapurine ribonucleosides (derived from 4-substituted thieno[2',3':4,5]pyrrolo[2,3-d]pyrimidines and thieno[3',2':4,5]pyrrolo[2,3-d]pyrimidines) were synthesized by a sequence involving Negishi coupling of 4,6-dichloropyrimidine with iodothiophenes, nucleophilic azidation, and cyclization of tetrazolopyrimidines, followed by glycosylation and cross-couplings or nucleophilic substitutions at position 4. Most nucleosides (from both isomeric series) exerted low micromolar or submicromolar in vitro cytostatic activities against a broad panel of Cancer and leukemia cell lines and some Antiviral activity against HCV. The most active were the 6-methoxy, 6-methylsulfanyl, and 6-methyl derivatives, which were highly active to Cancer cells and less toxic or nontoxic to fibroblasts.

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