title: Synthesis and Anti-HCV Activity of 4-Methoxy-7H-Pyrrolo[2,3-d] Pyrimidine Carbocyclic Nucleosides.
abstract: The present study includes the exploration of new possible nucleoside mimetics based on 4-methoxy-7H-pyrrolo[2,3-d]pyrimidine carbocyclic nucleosides (4a-g), which were synthesized by 10-15 synthetic steps and characterized adequately. We report the anti-HCV activities and cytotoxicities of 4a-g. Compound 4a was analyzed by single crystal X-ray diffraction which showed some puckering in the cyclopentene ring with a 2'-endo conformation and anti-base disposition (χ = -125.7°).
authors.affiliation: a Department of Chemistry , Birla Institute of Technology , Mesra , Ranchi , India.
authors.forename: Anandarajan
authors.initials: A
authors.lastname: Thiyagarajan
authors.affiliation: b Division of Antiviral Chemotherapy, Graduate School of Medical and Dental Sciences , Kagoshima University , Kagoshima , Japan.
authors.forename: Masaaki
authors.initials: M
authors.lastname: Toyama
authors.affiliation: b Division of Antiviral Chemotherapy, Graduate School of Medical and Dental Sciences , Kagoshima University , Kagoshima , Japan.
authors.forename: Masanori
authors.initials: M
authors.lastname: Baba
authors.affiliation: a Department of Chemistry , Birla Institute of Technology , Mesra , Ranchi , India.
authors.forename: Ashoke
authors.initials: A
authors.lastname: Sharon
authors.affiliation: a Department of Chemistry , Birla Institute of Technology , Mesra , Ranchi , India.
authors.forename: Chandralata
authors.initials: C
authors.lastname: Bal
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004353:Drug Evaluation, Preclinical; D016174:Hepacivirus / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011758:Pyrroles / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides; D011758:Pyrroles
keywords: 7H-pyrrolo[2,3-d]pyrimidine; Carbocyclic nucleosides; HCV; Selectfluor; tributylvinyltin; trimethylsilylacetylene