Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series

被引:57
|
作者
Amblard, F
Aucagne, V
Guenot, P
Schinazi, RF
Agrofoglio, LA
机构
[1] ICOA, UMR 6005, UFR Sci, Inst Chim Organ & Analyt, F-45067 Orleans 2, France
[2] Univ Rennes 1, CRMPO, F-35042 Rennes, France
[3] Emory Univ, Biochem Pharmacol Lab, Dept Pediat, Sch Med, Atlanta, GA 30033 USA
[4] Emory Univ, Sch Med, Vet Affairs Med Ctr, Atlanta, GA 30033 USA
基金
美国国家科学基金会;
关键词
nucleosides; furopyrimidine; antiviral activity;
D O I
10.1016/j.bmc.2004.11.057
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
The synthesis of novel acyclic nucleosides in the 5-alkynyl and 6-alkylfuro[2,3-d]pyrimidine series is described. These compounds were evaluated against HIV and HSV in order to determine their spectrum of antiviral activity. Their cytotoxicities against PBM, CEM and VERO cells were also determined. Compounds 21d and 24b displayed moderate EC50S of 2.7 and 4.9 muM, respectively, against HIV-1 and of 6.3 and 4.8 muM, respectively, against HSV. Nevertheless, these compounds also showed cellular toxicity, suggesting that the antiviral effects are secondary to the toxic effects. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1239 / 1248
页数:10
相关论文
共 50 条
  • [21] Synthesis of pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidine derivatives for antiviral evaluation
    Shamroukh, Ahmed H.
    Zaki, Magdi E. A.
    Morsy, Eman M. H.
    Abdel-Motti, Faiza M.
    Abdel-Megeid, Farouk M. E.
    ARCHIV DER PHARMAZIE, 2007, 340 (05) : 236 - 243
  • [22] Novel 5′-Norcarbocyclic Derivatives of Bicyclic Pyrrolo- and Furano[2,3-d]Pyrimidine Nucleosides
    Klimenko, Anna A.
    Matyugina, Elena S.
    Logashenko, Evgeniya B.
    Solyev, Pavel N.
    Zenkova, Marina A.
    Kochetkov, Sergey N.
    Khandazhinskaya, Anastasia L.
    MOLECULES, 2018, 23 (10):
  • [23] SYNTHESIS, ANTIPROLIFERATIVE, AND ANTIVIRAL ACTIVITY OF CERTAIN 4-AMINOPYRROLO(2,3-D)PYRIDAZINE NUCLEOSIDES - AN ENTRY INTO A NOVEL SERIES OF ADENOSINE-ANALOGS
    MEADE, EA
    WOTRING, LL
    DRACH, JC
    TOWNSEND, LB
    JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (03) : 526 - 533
  • [24] Pyrimidinethione as a building block in heterocyclic synthesis: synthesis of pyrano[2,3-d]pyrimidine, chromeno[2,3-d]pyrimidine, pyrido[3′,2′:5,6]pyrano[2,3-b]pyridine, and pyrimido[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives
    Reheim, Mohamed Ahmed Mahmoud Abdel
    Hafiz, Ibrahim Saad Abdel
    Elian, Mohamed Ahmed
    HETEROCYCLIC COMMUNICATIONS, 2016, 22 (06) : 311 - 317
  • [25] Bicyclic furano-, pyrrolo-, and thiopheno[2,3-d] derivatives of pyrimidine nucleosides: Synthesis and antiviral properties
    M. A. Ivanov
    L. A. Aleksandrova
    Russian Journal of Bioorganic Chemistry, 2013, 39 : 22 - 39
  • [26] Bicyclic furano-, pyrrolo-, and thiopheno[2,3-d] derivatives of pyrimidine nucleosides: Synthesis and antiviral properties
    Ivanov, M. A.
    Aleksandrova, L. A.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2013, 39 (01) : 22 - 39
  • [27] PYRIDINE AND PYRIDO[2,3-D]PYRIMIDINE DERIVATIVES WITH POTENTIAL ANTIVIRAL ACTIVITY
    RIDI, M
    CORTI, P
    LAZZI, L
    CHIMICA & L INDUSTRIA, 1969, 51 (02): : 202 - &
  • [28] A NOVEL SYNTHESIS OF PYRANO[2,3-D]PYRIMIDINE DERIVATIVES
    QUINTELA, JM
    PEINADOR, C
    MOREIRA, MJ
    TETRAHEDRON, 1995, 51 (20) : 5901 - 5912
  • [29] SYNTHESIS AND ANTITUBERCULOSIS ACTIVITY OF BENZOTHIENO[2,3-D]PYRIMIDINE
    KAPUSTINA, MV
    AMELKIN, OY
    KHARIZOMENOVA, IA
    SHVEDOV, VI
    FILITIS, LN
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1991, 25 (07): : 38 - 39
  • [30] Synthesis of certain 6-benzyl-5-methylthieno[2,3-d]pyrimidine
    El-Meligie, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1997, 36 (12): : 1126 - 1131