Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides

Michal Tichý, Radek Pohl, Hao Ying Xu, Yen Liang Chen, Fumiaki Yokokawa, Pei Yong Shi, Michal Hocek

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6123-6133
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number20
DOIs
StatePublished - Oct 15 2012

Keywords

  • Anti-dengue virus activity
  • Nucleosides
  • Pyrimido[4,5-b]indoles
  • Suzuki and Stille cross-coupling

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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