Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2′-deoxycytidine analogs

Wajdi Michel Zoghaib, Shajan Mannala, V. Sagar Gupta, Guy Tourigny

Research output: Contribution to journalArticle

Abstract

Analogs of (E)-5-(2-bromovinyl)-2′-deoxycytidine (BrVdCyd) (1) by substitution at N 4 were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N 4-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N 4-propanoyl-BrVdCyd (3) had good activity and N 4-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N 4-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.

Original languageEnglish
Pages (from-to)364-376
Number of pages13
JournalNucleosides, Nucleotides and Nucleic Acids
Volume31
Issue number4
DOIs
Publication statusPublished - Apr 1 2012

Fingerprint

Molecular Conformation
Deoxycytidine
Human Herpesvirus 1
Simplexvirus
Viruses
Conformations
Thermodynamic properties
Substitution reactions
Deamination
5-(2-bromovinyl)-2'-deoxycytidine
3'-deoxycytidine

Keywords

  • (E)-5-(2-bromovinyl)-2′-deoxycytidine
  • conformational analysis
  • Herpes simplex virus

ASJC Scopus subject areas

  • Genetics
  • Biochemistry
  • Molecular Medicine

Cite this

Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2′-deoxycytidine analogs. / Zoghaib, Wajdi Michel; Mannala, Shajan; Gupta, V. Sagar; Tourigny, Guy.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 31, No. 4, 01.04.2012, p. 364-376.

Research output: Contribution to journalArticle

@article{a6284f7ed6864195ac38c2e496061fa6,
title = "Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2′-deoxycytidine analogs",
abstract = "Analogs of (E)-5-(2-bromovinyl)-2′-deoxycytidine (BrVdCyd) (1) by substitution at N 4 were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N 4-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N 4-propanoyl-BrVdCyd (3) had good activity and N 4-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N 4-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.",
keywords = "(E)-5-(2-bromovinyl)-2′-deoxycytidine, conformational analysis, Herpes simplex virus",
author = "Zoghaib, {Wajdi Michel} and Shajan Mannala and Gupta, {V. Sagar} and Guy Tourigny",
year = "2012",
month = "4",
day = "1",
doi = "10.1080/15257770.2012.661214",
language = "English",
volume = "31",
pages = "364--376",
journal = "Nucleosides, Nucleotides and Nucleic Acids",
issn = "1525-7770",
publisher = "Taylor and Francis Ltd.",
number = "4",

}

TY - JOUR

T1 - Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2′-deoxycytidine analogs

AU - Zoghaib, Wajdi Michel

AU - Mannala, Shajan

AU - Gupta, V. Sagar

AU - Tourigny, Guy

PY - 2012/4/1

Y1 - 2012/4/1

N2 - Analogs of (E)-5-(2-bromovinyl)-2′-deoxycytidine (BrVdCyd) (1) by substitution at N 4 were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N 4-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N 4-propanoyl-BrVdCyd (3) had good activity and N 4-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N 4-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.

AB - Analogs of (E)-5-(2-bromovinyl)-2′-deoxycytidine (BrVdCyd) (1) by substitution at N 4 were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N 4-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N 4-propanoyl-BrVdCyd (3) had good activity and N 4-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N 4-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.

KW - (E)-5-(2-bromovinyl)-2′-deoxycytidine

KW - conformational analysis

KW - Herpes simplex virus

UR - http://www.scopus.com/inward/record.url?scp=84859166375&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84859166375&partnerID=8YFLogxK

U2 - 10.1080/15257770.2012.661214

DO - 10.1080/15257770.2012.661214

M3 - Article

VL - 31

SP - 364

EP - 376

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

SN - 1525-7770

IS - 4

ER -