Synthesis of 9-membered masked enediyne analogues possessing DNA intercalator and sugar moieties

被引:13
|
作者
Takahashi, T [1 ]
Tanaka, H [1 ]
Matsuda, A [1 ]
Doi, T [1 ]
Yamada, H [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem Engn, Meguro Ku, Tokyo 1528552, Japan
关键词
D O I
10.1016/S0960-894X(98)00605-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Syntheses of hybrid DNA cleaving molecules which have the 9-membered enediyne structure of kedarcidin with the DNA intercalator of NCS and/or the sugar moieties were accomplished. Introduction of the sugar moieties to the masked enediyne was achieved via S-alkylation of a bromoacetate derivative with a sugar-containing thiol without the need for protection of the sugar moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3299 / 3302
页数:4
相关论文
共 50 条
  • [1] DNA cleaving activities of 9-membered masked enediyne analogues possessing DNA intercalator and sugar moieties
    Takahashi, T
    Tanaka, H
    Matsuda, A
    Doi, T
    Yamada, H
    Matsumoto, T
    Sasaki, D
    Sugiura, Y
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (23) : 3303 - 3306
  • [2] Recent progress in syntheses of 9-membered masked enediyne analogues and their DNA cleaving activities
    Takahashi, T
    Tanaka, H
    Doi, T
    Yamada, H
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1998, 56 (11) : 987 - 999
  • [3] An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked Enediyne Using an Automated Synthesizer
    Tanaka, Yoshikazu
    Fuse, Shinichiro
    Tanaka, Hiroshi
    Doi, Takayuki
    Takahashi, Takashi
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (06) : 1111 - 1121
  • [4] Synthesis of nine-membered, masked enediyne analogues with DNA intercalators and its DNA cleaving activities
    Takahashi, T
    Tanaka, H
    Yamada, H
    Matsumoto, T
    Sugiura, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1524 - 1526
  • [5] Total synthesis of 9-membered enediyne antibiotic N1999-A2: Absolute stereochemistry and DNA cleavage
    Kobayashi, S
    Hirama, M
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2004, 62 (03) : 184 - 193
  • [6] A NOVEL SYNTHESIS OF A 9-MEMBERED RING
    HUFF, RK
    MOPPETT, CE
    SUTHERLA.JK
    [J]. CHEMICAL COMMUNICATIONS, 1968, (19) : 1192 - &
  • [7] Discovery of pentaene polyols by the activation of an enediyne gene cluster: biosynthetic implications for 9-membered enediyne core structures
    Pan, Jian
    Tan, Qingwen
    Zhu, Saibin
    Yan, Xiaohui
    Li, Yu
    Zhuang, Zhoukang
    Zhu, Xiangcheng
    Duan, Yanwen
    Huang, Yong
    [J]. CHEMICAL SCIENCE, 2022, 13 (45) : 13475 - 13481
  • [8] 9-Membered Carbocycles: Strategies and Tactics for their Synthesis
    Huber, Tatjana
    Wildermuth, Raphael E.
    Magauer, Thomas
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (47) : 12107 - 12120
  • [9] SYNTHESIS OF A 9-MEMBERED CYCLIC ANALOG OF THE NEOCARZINOSTATIN CHROMOPHORE AND ITS DNA-CLEAVING ACTIVITY
    TAKAHASHI, T
    TANAKA, H
    HIRAI, Y
    DOI, T
    YAMADA, H
    SHIRAKI, T
    SUGIURA, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (11): : 1657 - 1659
  • [10] SYNTHESIS OF 9-MEMBERED HETEROCYCLES VIA BETA-LACTAMS
    BOSE, AK
    HOFFMAN, WH
    MANHAS, MS
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1976, 172 (SEP3): : 60 - 60