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

doi:10.1016/j.bmc.2012.08.021

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

Biochemistry & Molecular Biology

Research output: Contribution to journal › Article › peer-review

57 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 language	English (US)
Pages (from-to)	6123-6133
Number of pages	11
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	20
DOIs	https://doi.org/10.1016/j.bmc.2012.08.021
State	Published - 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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10.1016/j.bmc.2012.08.021

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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.",

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

author = "Michal Tich{\'y} and Radek Pohl and Xu, \{Hao Ying\} and Chen, \{Yen Liang\} and Fumiaki Yokokawa and Shi, \{Pei Yong\} and Michal Hocek",

note = "Funding Information: This work was supported by the Academy of Sciences of the Czech Republic (RVO: 61388963), Czech Science Foundation (P207/11/0344) and by Gilead Sciences, Inc. We would like to thank Feng Gu, Kah Fei Wan and Chang Bok Lee for assisting with testing the compounds. ",

year = "2012",

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day = "15",

doi = "10.1016/j.bmc.2012.08.021",

language = "English (US)",

volume = "20",

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T1 - Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides

AU - Tichý, Michal

AU - Pohl, Radek

AU - Xu, Hao Ying

AU - Chen, Yen Liang

AU - Yokokawa, Fumiaki

AU - Shi, Pei Yong

AU - Hocek, Michal

N1 - Funding Information: This work was supported by the Academy of Sciences of the Czech Republic (RVO: 61388963), Czech Science Foundation (P207/11/0344) and by Gilead Sciences, Inc. We would like to thank Feng Gu, Kah Fei Wan and Chang Bok Lee for assisting with testing the compounds.

PY - 2012/10/15

Y1 - 2012/10/15

N2 - 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.

AB - 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.

KW - Anti-dengue virus activity

KW - Nucleosides

KW - Pyrimido[4,5-b]indoles

KW - Suzuki and Stille cross-coupling

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UR - https://www.scopus.com/pages/publications/84866950720#tab=citedBy

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DO - 10.1016/j.bmc.2012.08.021

M3 - Article

C2 - 22985963

AN - SCOPUS:84866950720

SN - 0968-0896

VL - 20

SP - 6123

EP - 6133

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 20

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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