title: Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides.
abstract: A series of new pyrimido[4,5-b]indole ribonucleosides bearing phenyl or hetaryl group at position 4 has been prepared by selective Pd-catalyzed cross-coupling reactions of the corresponding protected 4,6-dichloropyrimido[4,5-b]indole ribonucleoside with (het)arylboronic acids or stannanes followed by deprotection. Further cross-couplings under harsher conditions and employing X-Phos ligand proceeded at the position 6 leading to 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides. Some of these compounds displayed antiviral activity against Dengue virus.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
authors.forename: Michal
authors.initials: M
authors.lastname: Tichý
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Hao Ying
authors.initials: HY
authors.lastname: Xu
authors.forename: Yen-Liang
authors.initials: YL
authors.lastname: Chen
authors.forename: Fumiaki
authors.initials: F
authors.lastname: Yokokawa
authors.forename: Pei-Yong
authors.initials: PY
authors.lastname: Shi
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003716:Dengue Virus / Q000187:drug effects / Q000378:metabolism; D056945:Hep G2 Cells; D016174:Hepacivirus / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D010165:Palladium; D011743:Pyrimidines / Q000737:chemistry*; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D007211:Indoles; D011743:Pyrimidines; D012263:Ribonucleosides; D010165:Palladium; C030374:indole; C030986:pyrimidine