Synthesis of New Cyclic and Acyclic 5-Halouridine Derivatives as Potential Antiviral Agents

被引：8
|
作者：
Elshehry, Mohamed F. [1 ,2 ]
Balzarini, Jan [3 ]
Meier, Chris [1 ]
机构：
[1] Univ Hamburg, Fac Sci, Dept Chem, D-20146 Hamburg, Germany
[2] Natl Res Ctr, Pesticide Dept, Cairo 12622, Egypt
[3] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
来源：
SYNTHESIS-STUTTGART | 2009年 / 05期
关键词：
bioorganic chemistry; drugs; antiviral agents; nucleosides; glycosylation; IMMUNODEFICIENCY-VIRUS TYPE-1; GENERAL SYNTHESIS; N-GLYCOSIDES; HIV; NUCLEOSIDES; TOXICITY; SERIES; AZT;
D O I：
10.1055/s-0028-1083369
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of new cyclic and acyclic nucleoside analogues was achieved by alkylation of 5-halogenated 6-(2,4-dichlorophenoxymethyl)pyrimidine-2,4-dione following the Vorbruggen coupling procedure. Nucleoside analogues of the 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)-type were obtained as well as analogues of ganciclovir, acyclovir, and ribonucleosides. All compounds were tested against a variety of viruses. Three of the new compounds were potent and selective anti-HIV-1 inhibitors.
引用
收藏
页码：841 / 847
页数：7
相关论文
共 50 条
  • [31] Synthesis and antiviral evaluation of cyclic and acyclic 2-methyl-3-hydroxy-4-pyridinone nucleoside derivatives
    Barral, K
    Balzarini, J
    Neyts, J
    De Clercq, E
    Hider, RC
    Camplo, M
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (01) : 43 - 50
  • [32] STUDIES ON ANTIVIRAL AGENTS .1. SYNTHESIS AND INVITRO ANTIVIRAL ACTIVITY OF NEW KANAMYCIN A DERIVATIVES
    MATSUDA, K
    YASUDA, N
    TSUTSUMI, H
    TAKAYA, T
    JOURNAL OF ANTIBIOTICS, 1985, 38 (04): : 547 - 549
  • [33] SYNTHESIS AND ANTIVIRAL EVALUATION OF FUROPYRIMIDINE DIONES CYCLIC AND ACYCLIC, NUCLEOSIDE ANALOGS
    RENAULT, J
    JOURDAN, F
    LADUREE, D
    ROBBA, M
    HETEROCYCLES, 1995, 41 (05) : 937 - 945
  • [34] SYNTHESIS OF NEW BENZIMIDAZOLE DERIVATIVES AS POTENTIAL ANTIMICROBIAL AGENTS
    BADAWEY, ESAM
    HASSAN, AMM
    KAPPE, T
    ARCHIV DER PHARMAZIE, 1991, 324 (06) : 355 - 357
  • [35] Synthesis of new indazole derivatives as potential antioxidant agents
    Sapnakumari, Majal
    Narayana, Badiadka
    Sarojini, Balladka Kunhanna
    Madhu, Leelavathi Narayana
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (05) : 2368 - 2376
  • [36] Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents
    Napiorkowska, Mariola
    Cieslak, Marcin
    Kazmierczak-Baranska, Julia
    Krolewska-Golinska, Karolina
    Nawrot, Barbara
    MOLECULES, 2019, 24 (08)
  • [37] Synthesis of new indazole derivatives as potential antioxidant agents
    Majal Sapnakumari
    Badiadka Narayana
    Balladka Kunhanna Sarojini
    Leelavathi Narayana Madhu
    Medicinal Chemistry Research, 2014, 23 : 2368 - 2376
  • [38] Synthesis of Cyclic and Acyclic Pyrimidine Nucleosides Analogues with Anticipated Antiviral Activity
    El-Shehry, Mohamed F.
    El Telbani, Emad M.
    Hegab, Mohamed I.
    ACTA CHIMICA SLOVENICA, 2018, 65 (02) : 401 - 406
  • [39] Synthesis of alkenyl acyclonucleosides derivatives of 5-halogenouracil as antiviral and antitumoral agents
    Rochdi, A
    Taourirte, M
    Redwane, N
    Lazrek, HB
    Barascut, JL
    Imbach, JL
    NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (4-5): : 673 - 674
  • [40] SYNTHESIS OF SOME NEW 3-(3'-CARBOXYPHENYLTHIOSEMICARBAZONO)-2-INDOLINONE DERIVATIVES AS POTENTIAL ANTIVIRAL AGENTS
    SHUKLA, SK
    SINGH, SP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (07): : 697 - 699
12345