title: Synthesis and biological activity of benzo-fused 7-deazaadenosine analogues. 5- and 6-substituted 4-amino- or 4-alkylpyrimido[4,5-b]indole ribonucleosides.
abstract: Two series of new 4-aminopyrimido[4,5-b]indole ribonucleosides bearing phenyl or hetaryl group at position 5 or 6 have been prepared by Suzuki or Stille cross-coupling reactions employing X-Phos ligand with (het)arylboronic acids or stannanes. A series of 4-substituted nucleosides has been also prepared by Pd-catalyzed cross-couplings or nucleophilic substitution. Some of these compounds displayed moderate antiviral activities against HCV and dengue viruses.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic.
authors.forename: Michal
authors.initials: M
authors.lastname: Tichý
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Eva
authors.initials: E
authors.lastname: Tloušt'ová
authors.forename: Jan
authors.initials: J
authors.lastname: Weber
authors.forename: Gina
authors.initials: G
authors.lastname: Bahador
authors.forename: Yu-Jen
authors.initials: YJ
authors.lastname: Lee
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003716:Dengue Virus / Q000187:drug effects; D018922:HL-60 Cells; D006367:HeLa Cells; D056945:Hep G2 Cells; D016174:Hepacivirus / Q000187:drug effects; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity
chemical_list: D000998:Antiviral Agents; D007211:Indoles; D012263:Ribonucleosides; D010165:Palladium; C030374:indole; D000241:Adenosine
keywords: Anti-dengue virus activity; Nucleosides; Pyrimido[4,5-b]indoles; Suzuki and Stille cross-coupling