Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

被引:9
作者
Yoshimura, Yuichi [1 ]
Saito, Yukako [1 ]
Natori, Yoshihiro [1 ]
Wakamatsu, Hideaki [1 ]
机构
[1] Tohoku Med & Pharmaceut Univ, Fac Pharmaceut Sci, Aoba Ku, 4-4-1 Komatsushima, Sendai, Miyagi 9818558, Japan
基金
日本学术振兴会;
关键词
nucleoside; antitumor; antiviral; 4 '-thionucleoside; antiherpes virus; Pummerer reaction; IMMUNODEFICIENCY-VIRUS TYPE-1; ANTI-HERPESVIRUS ACTIVITY; IN-VITRO; PYRIMIDINE NUCLEOSIDES; BIOLOGICAL-ACTIVITIES; GEMCITABINE; 1-(2-DEOXY-2-FLUORO-4-THIO-BETA-D-ARABINOFURANOSYL)CYTOSINE; ENANTIOMERS; DERIVATIVES; HIV;
D O I
10.1248/cpb.c17-00636
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Many attempts have been made to synthesize structurally novel nucleoside derivatives in order to identify effective compounds for the treatment of tumors and virus-caused disease. At our laboratories, as part of our efforts to synthesize 4'-thionucleosides, we have identified and characterized biologically active nucleosides. During the course of our synthetic study, we developed the Pummerer-type thioglycosylation reaction. As a result, we synthesized a potent antineoplastic nucleoside, 1-(2-deoxy-2-fiuoro-beta-D-4-thio-arabino-furanosyl)cytosine (4'-thioFAC), and several novel 4'-thionucleosides that possess antiherpes virus activities.
引用
收藏
页码:139 / 146
页数:8
相关论文
共 54 条
  • [11] SYNTHESIS AND PROPERTIES OF NUCLEOTIDES CONTAINING 4-THIO-D-RIBOFURANOSE
    HOFFMAN, DJ
    WHISTLER, RL
    [J]. BIOCHEMISTRY, 1970, 9 (11) : 2367 - &
  • [12] Action of Anti-HIV drugs and resistance: Reverse transcriptase inhibitors and protease inhibitors
    Imamichi, T
    [J]. CURRENT PHARMACEUTICAL DESIGN, 2004, 10 (32) : 4039 - 4053
  • [13] KITA Y, 1985, CHEM PHARM BULL, V33, P4235
  • [14] THE CHEMISTRY OF O-SILYLATED KETENE ACETAL - PUMMERER REARRANGEMENT OF SULFOXIDES INTO ALPHA-SILOXYSULFIDES
    KITA, Y
    YASUDA, H
    TAMURA, O
    ITOH, F
    TAMURA, Y
    [J]. TETRAHEDRON LETTERS, 1984, 25 (41) : 4681 - 4682
  • [15] Synthesis of novel pyrimidine apiothionucleosides and in vitro evaluation of their cytotoxicity
    Kotoulas, Stefanos S.
    Kojic, Vesna V.
    Bogdanovic, Gordana M.
    Koumbis, Alexandros E.
    [J]. TETRAHEDRON, 2015, 71 (21) : 3396 - 3403
  • [16] Synthesis and cytotoxic evaluation of novel pyrimidine deoxyapiothionucleosides
    Kotoulas, Stefanos S.
    Kojic, Vesna V.
    Bogdanovic, Gordana M.
    Koumbis, Alexandros E.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (11) : 3364 - 3367
  • [17] Anti-herpesvirus activity profile of 4′-thioarabinofuranosyl purine and uracil nucleosides and activity of 1-β-D-2′-fluoro-4′-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus
    Machida, H
    Ashida, N
    Miura, S
    Endo, M
    Yamada, K
    Kitano, K
    Yoshimura, Y
    Sakata, S
    Ijichi, O
    Eizuru, Y
    [J]. ANTIVIRAL RESEARCH, 1998, 39 (02) : 129 - 137
  • [18] MACHIDA H, 1993, NUCLEOSIDES AND NUCLEOTIDES AS ANTITUMOR AND ANTIVIRAL AGENTS, P245
  • [19] L-Nucleoside enantiomers as antivirals drugs:: A mini-review
    Mathe, Christophe
    Gosselin, Gilles
    [J]. ANTIVIRAL RESEARCH, 2006, 71 (2-3) : 276 - 281
  • [20] NUCLEOSIDES AND NUCLEOTIDES .97. SYNTHESIS OF NEW BROAD-SPECTRUM ANTINEOPLASTIC NUCLEOSIDES, 2'-DEOXY-2'-METHYLIDENECYTIDINE (DMDC) AND ITS DERIVATIVES
    MATSUDA, A
    TAKENUKI, K
    TANAKA, M
    SASAKI, T
    UEDA, T
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) : 812 - 819