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 journalArticle

26 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Ribonucleosides
Antiviral Agents
Bearings (structural)
Dengue Virus
Cross Reactions
Viruses
Ligands
Acids
indole

Keywords

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

ASJC Scopus subject areas

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

Cite this

Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides. / Tichý, Michal; Pohl, Radek; Xu, Hao Ying; Chen, Yen Liang; Yokokawa, Fumiaki; Shi, Pei-Yong; Hocek, Michal.

In: Bioorganic and Medicinal Chemistry, Vol. 20, No. 20, 15.10.2012, p. 6123-6133.

Research output: Contribution to journalArticle

Tichý, Michal ; Pohl, Radek ; Xu, Hao Ying ; Chen, Yen Liang ; Yokokawa, Fumiaki ; Shi, Pei-Yong ; Hocek, Michal. / Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides. In: Bioorganic and Medicinal Chemistry. 2012 ; Vol. 20, No. 20. pp. 6123-6133.
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