Nucleosides, Nucleotides and Nucleic Acids

, volume 24 , issue 10-12 , pages 1417-1437

Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides

Jiong J Chen ¹

Wei Yuan ¹

John D. Williams ²

JOHN C. DRACH ^{2, 3}

LEROY B. TOWNSEND ^{1, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

a Department of Chemistry , College of Literature, Sciences and the Arts, University of Michigan , Ann Arbor, Michigan, USA |

b Department of Medicinal Chemistry , College of Pharmacy, University of Michigan , Ann Arbor, Michigan, USA |

c Department of Biologic and Materials Sciences , School of Dentistry, University of Michigan , Ann Arbor, Michigan, USA |

Publication type: Journal Article

Publication date: 2005-09-01

Taylor & Francis

Nucleosides, Nucleotides and Nucleic Acids

scimago Q3

wos Q4

SJR: 0.312

CiteScore: 2.1

Impact factor: 1.3

ISSN: 15257770, 15322335

DOI: 10.1080/15257770500265646

Copy DOI

PubMed ID: 16438026

Biochemistry

General Medicine

Genetics

Molecular Medicine

Abstract

2,5, 6-Trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB), 2-bromo-5, 6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB) and 2-benzylthio-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BTDCRB) are benzimidazole nucleosides that exhibit strong and selective anti-HCMV activity. Polyhalogenated indole C-nucleosides were prepared as 1-deaza analogs of the benzimidazole nucleosides TCRB and BDCRB. A mild Knoevenagel coupling reaction between an indol-2-thione and a ribofuranose derivative was developed for the synthesis of 2-benzylthio-5, 6-dichloro-3-(beta-D-ribofuranosyl)indole (12). 3-(beta-D-ribofuranosyl)-2,5,6-trichloroindole (16) was prepared from 12 in 4 steps. A Lewis acid-mediated glycosylation method was then developed to prepare the targeted 2-haloindole C-nucleoside 16 stereoselectively in four steps from the corresponding 2-haloindole aglycons. Only 12 was active against HCMV but it also was somewhat cytotoxic.

Found

1 citation

Shchepochkin Alexandr

PhD in Chemistry

35 publications, 524 citations, 1 review

h-index: 13

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Ural Federal University

Research interests

"Smart" materials

Green chemistry

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Chen J. J. et al. Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides // Nucleosides, Nucleotides and Nucleic Acids. 2005. Vol. 24. No. 10-12. pp. 1417-1437.

GOST all authors (up to 50) Copy

Chen J. J., Yuan W., Williams J. D., DRACH J. C., TOWNSEND L. B. Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides // Nucleosides, Nucleotides and Nucleic Acids. 2005. Vol. 24. No. 10-12. pp. 1417-1437.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1080/15257770500265646

UR - https://doi.org/10.1080/15257770500265646

TI - Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides

T2 - Nucleosides, Nucleotides and Nucleic Acids

AU - Chen, Jiong J

AU - Yuan, Wei

AU - Williams, John D.

AU - DRACH, JOHN C.

AU - TOWNSEND, LEROY B.

PY - 2005

DA - 2005/09/01

PB - Taylor & Francis

SP - 1417-1437

IS - 10-12

VL - 24

PMID - 16438026

SN - 1525-7770

SN - 1532-2335

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2005_Chen,

author = {Jiong J Chen and Wei Yuan and John D. Williams and JOHN C. DRACH and LEROY B. TOWNSEND},

title = {Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides},

journal = {Nucleosides, Nucleotides and Nucleic Acids},

year = {2005},

volume = {24},

publisher = {Taylor & Francis},

month = {sep},

url = {https://doi.org/10.1080/15257770500265646},

number = {10-12},

pages = {1417--1437},

doi = {10.1080/15257770500265646}

}

MLA

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MLA Copy

Chen, Jiong J., et al. “Design, Synthesis, and Antiviral Evaluation of Some Polyhalogenated Indole C-nucleosides.” Nucleosides, Nucleotides and Nucleic Acids, vol. 24, no. 10-12, Sep. 2005, pp. 1417-1437. https://doi.org/10.1080/15257770500265646.

Publisher

Taylor & Francis

Journal

Nucleosides, Nucleotides and Nucleic Acids

scimago Q3

wos Q4

SJR

0.312

CiteScore

2.1

Impact factor

1.3

ISSN

15257770 (Print)

15322335 (Electronic)