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
N1 - Funding Information:
Received 10 January 2012; accepted 23 January 2012. This research was funded by grants from the Medical Research Council of Canada to Dr. V. S. Gupta, Grant No. MA 10254. The corresponding author wishes to thank Dr. Sashi Kumar and Dr. Allan Stuart for their constructive advice and helpful discussions. Address correspondence to Wajdi Michel Zoghaib, Department of Chemistry, Sultan Qaboos University, P.O. Box 36, Al-Khod, 123, Oman. E-mail: zoghaibw@squ.edu.om
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 - Herpes simplex virus
KW - conformational analysis
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U2 - 10.1080/15257770.2012.661214
DO - 10.1080/15257770.2012.661214
M3 - Article
C2 - 22444197
AN - SCOPUS:84859166375
SN - 1525-7770
VL - 31
SP - 364
EP - 376
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 4
ER -