SYNTHESIS, MOLECULAR CONFORMATION AND ACTIVITY AGAINST HERPES SIMPLEX VIRUS OF (E)-5-(2-BROMOVINYL)-2′-DEOXYCYTIDINE ANALOGS

被引：0
|
作者：
Zoghaib, Wajdi Michel [1 ]
Mannala, Shajan [3 ]
Gupta, V. Sagar [3 ]
Tourigny, Guy [2 ]
机构：
[1] Sultan Qaboos Univ, Dept Chem, Al Khoud 123, Oman
[2] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 0W0, Canada
[3] Univ Saskatchewan, Dept Biomed Sci, Saskatoon, SK S7N 0W0, Canada
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2012年 / 31卷 / 04期
基金：
英国医学研究理事会;
关键词：
Herpes simplex virus; (E)-5-(2-bromovinyl)-2 '-deoxycytidine; conformational analysis; CRYSTAL-STRUCTURES; THYMIDINE KINASE; 5-METHOXYMETHYL-2'-DEOXYCYTIDINE; NUCLEOSIDES; DNA;
D O I：
10.1080/15257770.2012.661214
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
引用
收藏
页码：364 / 376
页数：13
相关论文
共 50 条
  • [1] SYNTHESIS AND ANTIVIRAL ACTIVITY OF (E)-5-(2-BROMOVINYL)URACIL AND (E)-5-(2-BROMOVINYL)URIDINE
    DECLERCQ, E
    DESGRANGES, C
    HERDEWIJN, P
    SIM, IS
    JONES, AS
    MCLEAN, MJ
    WALKER, RT
    JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (02) : 213 - 217
  • [2] TREATMENT OF EXPERIMENTAL HERPES-SIMPLEX VIRUS ENCEPHALITIS WITH (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE IN MICE
    DECLERCQ, E
    ZHANG, ZX
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1982, 22 (03) : 421 - 425
  • [3] PROBLEMS ASSOCIATED WITH THE USE OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE FOR TYPING HERPES-SIMPLEX VIRUS
    SWIERKOSZ, EM
    ARENS, MQ
    RIVETNA, KA
    JOURNAL OF CLINICAL MICROBIOLOGY, 1985, 21 (03) : 459 - 461
  • [4] SYNTHESIS OF 3'-MODIFIED ANALOGS OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE
    DYATKINA, NB
    KRAYEVSKY, AA
    GERMAN, G
    JANTALIPINSKI, M
    LANGEN, P
    YARTSEVA, IV
    BIOORGANICHESKAYA KHIMIYA, 1986, 12 (03): : 408 - 415
  • [5] (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE IN THE TREATMENT OF EXPERIMENTAL HERPES-SIMPLEX KERATITIS
    MAUDGAL, PC
    DECLERCQ, E
    DESCAMPS, J
    MISSOTTEN, L
    DESOMER, P
    BUSSON, R
    VANDERHAEGHE, H
    VERHELST, G
    WALKER, RT
    JONES, AS
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1980, 17 (01) : 8 - 12
  • [6] EFFECT OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE ON SYNTHESIS OF HERPES-SIMPLEX VIRUS TYPE-1-SPECIFIC POLYPEPTIDES
    SIEGEL, SA
    OTTO, MJ
    DECLERCQ, E
    PRUSOFF, WH
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1984, 25 (05) : 566 - 570
  • [7] EFFICACY OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE IN THE TREATMENT OF EXPERIMENTAL HERPES-SIMPLEX VIRUS ENCEPHALITIS IN MICE
    PARK, NH
    PAVANLANGSTON, D
    DECLERCQ, E
    ANTIVIRAL RESEARCH, 1983, 3 (01) : 7 - 15
  • [8] SYNTHESIS AND ANTIVIRAL PROPERTIES OF (E)-5-(2-BROMOVINYL)-2'-DEOXYCYTIDINE-RELATED COMPOUNDS
    JONES, AS
    SAYERS, JR
    WALKER, RT
    DECLERCQ, E
    JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) : 268 - 271
  • [9] EFFICACY OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE IN THE TOPICAL TREATMENT OF HERPES-SIMPLEX KERATITIS
    MAUDGAL, PC
    MISSOTTEN, L
    DECLERCQ, E
    DESCAMPS, J
    DEMEUTER, E
    ALBRECHT VON GRAEFES ARCHIV FUR KLINISCHE UND EXPERIMENTELLE OPHTHALMOLOGIE, 1981, 216 (04): : 261 - 268
  • [10] HERPES-SIMPLEX VIRUS TYPE-1 THAT EXHIBITS HERPES-SIMPLEX VIRUS TYPE-2 SENSITIVITY TO (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE
    DOCHERTY, JJ
    DOBSON, AT
    TRIMBLE, JJ
    JENNINGS, BA
    INTERVIROLOGY, 1991, 32 (05) : 308 - 315
12345