Synthesis, conformation, and antiviral activity of 5-methoxymethyl-2′-deoxycytidine analogs

Wajdi M. Zoghaib; Shajan Mannala; V. Sagar Gupta; Guy Tourigny; R. Stephen Reid

doi:10.1081/NCN-120019532

Synthesis, conformation, and antiviral activity of 5-methoxymethyl-2′-deoxycytidine analogs

Wajdi M. Zoghaib^*, Shajan Mannala, V. Sagar Gupta, Guy Tourigny, R. Stephen Reid

^*Corresponding author for this work

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

3 Citations (Scopus)

Abstract

Analogs of 5-methoxymethyl-2′-deoxycytidine, MMdCyd (1) by substitution at N⁴ were synthesized to impart resistance against deamination. The anti HSV-1 activity and solution conformation of analogs were determined. N⁴-Butanoyl-MMdCyd (10) was a potent inhibitor of HSV-1 replication while N⁴-hexanoyl-MMdCyd (11), N⁴-propanoyl-MMdCyd (9) and N⁴-acetyl-MMdCyd (8) had good activity against HSV-1 replication. All other analogs were devoid of activity against HSV-1.

Original language	English
Pages (from-to)	223-238
Number of pages	16
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	22
Issue number	2
DOIs	https://doi.org/10.1081/NCN-120019532
Publication status	Published - 2003
Externally published	Yes

Keywords

5-methoxymethyl-2′-deoxycytidine
Conformation
Herpes Simplex Virus

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Genetics

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10.1081/NCN-120019532

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title = "Synthesis, conformation, and antiviral activity of 5-methoxymethyl-2′-deoxycytidine analogs",

abstract = "Analogs of 5-methoxymethyl-2′-deoxycytidine, MMdCyd (1) by substitution at N4 were synthesized to impart resistance against deamination. The anti HSV-1 activity and solution conformation of analogs were determined. N4-Butanoyl-MMdCyd (10) was a potent inhibitor of HSV-1 replication while N4-hexanoyl-MMdCyd (11), N4-propanoyl-MMdCyd (9) and N4-acetyl-MMdCyd (8) had good activity against HSV-1 replication. All other analogs were devoid of activity against HSV-1.",

keywords = "5-methoxymethyl-2′-deoxycytidine, Conformation, Herpes Simplex Virus",

author = "Zoghaib, {Wajdi M.} and Shajan Mannala and Gupta, {V. Sagar} and Guy Tourigny and Reid, {R. Stephen}",

note = "Funding Information: This research was funded by grants from the Medical Research Council of Canada to Dr. V. S. Gupta, grant: MA 10254. The authors wish to thank the College of Graduate Studies and Research, University of Saskatchewan, for scholarship support to Mr. Wajdi Michel Zoghaib and Mr. Shajan Mannala, and the Department of Chemistry, University of Saskatchewan, for providing funds for consumables. The authors also wish to thank Dr. Sashi Kumar and Dr. Allan Stuart for their constructive advice and helpful discussions.",

year = "2003",

doi = "10.1081/NCN-120019532",

language = "English",

volume = "22",

pages = "223--238",

journal = "Nucleosides, Nucleotides and Nucleic Acids",

issn = "1525-7770",

number = "2",

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T1 - Synthesis, conformation, and antiviral activity of 5-methoxymethyl-2′-deoxycytidine analogs

AU - Zoghaib, Wajdi M.

AU - Mannala, Shajan

AU - Gupta, V. Sagar

AU - Tourigny, Guy

AU - Reid, R. Stephen

N1 - Funding Information: This research was funded by grants from the Medical Research Council of Canada to Dr. V. S. Gupta, grant: MA 10254. The authors wish to thank the College of Graduate Studies and Research, University of Saskatchewan, for scholarship support to Mr. Wajdi Michel Zoghaib and Mr. Shajan Mannala, and the Department of Chemistry, University of Saskatchewan, for providing funds for consumables. The authors also wish to thank Dr. Sashi Kumar and Dr. Allan Stuart for their constructive advice and helpful discussions.

PY - 2003

Y1 - 2003

N2 - Analogs of 5-methoxymethyl-2′-deoxycytidine, MMdCyd (1) by substitution at N4 were synthesized to impart resistance against deamination. The anti HSV-1 activity and solution conformation of analogs were determined. N4-Butanoyl-MMdCyd (10) was a potent inhibitor of HSV-1 replication while N4-hexanoyl-MMdCyd (11), N4-propanoyl-MMdCyd (9) and N4-acetyl-MMdCyd (8) had good activity against HSV-1 replication. All other analogs were devoid of activity against HSV-1.

AB - Analogs of 5-methoxymethyl-2′-deoxycytidine, MMdCyd (1) by substitution at N4 were synthesized to impart resistance against deamination. The anti HSV-1 activity and solution conformation of analogs were determined. N4-Butanoyl-MMdCyd (10) was a potent inhibitor of HSV-1 replication while N4-hexanoyl-MMdCyd (11), N4-propanoyl-MMdCyd (9) and N4-acetyl-MMdCyd (8) had good activity against HSV-1 replication. All other analogs were devoid of activity against HSV-1.

KW - 5-methoxymethyl-2′-deoxycytidine

KW - Conformation

KW - Herpes Simplex Virus

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JO - Nucleosides, Nucleotides and Nucleic Acids

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SN - 1525-7770

IS - 2

ER -

Synthesis, conformation, and antiviral activity of 5-methoxymethyl-2′-deoxycytidine analogs

Abstract

Keywords

ASJC Scopus subject areas

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