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

Chemistry

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

Keywords

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

ASJC Scopus subject areas

Biochemistry
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.",

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AU - Zoghaib, Wajdi M.

AU - Mannala, Shajan

AU - Gupta, V. Sagar

AU - Tourigny, Guy

AU - Reid, R. Stephen

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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.

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