Synthesis and biological evaluation of QRSTUVWXYZA′ domains of maitotoxin

被引:0
|
作者
机构
[1] Nicolaou, K.C.
[2] Heretsch, Philipp
[3] Nakamura, Tsuyoshi
[4] Rudo, Anna
[5] Murata, Michio
[6] Konoki, Keiichi
来源
Nicolaou, K.C. | 1600年 / American Chemical Society卷 / 136期
关键词
The synthesis of QRSTUVWXYZA′ domains 7; 8; and 9 of the highly potent marine neurotoxin maitotoxin (1); the largest secondary metabolite isolated to date; is described. The devised synthetic strategy entailed a cascade Takai-Utimoto ester olefination/ring closing metathesis to construct ring Y; a hydroxydithioketal cyclization/methylation sequence to cast ring X; a Horner-Wadsworth-Emmons coupling of WXYZA′ ketophosphonate 11 with QRSTU aldehyde 12 to form enone 10; and a reductive hydroxyketone ring closure to forge ring V. 2D NMR spectroscopic analysis and comparison of 13C chemical shifts with those of the corresponding carbons of maitotoxin revealed close similarities supporting the originally assigned structure of this region of the natural product. Biological evaluations of various synthesized domains of maitotoxin in this and previous studies from these laboratories led to fragment structure-activity relationships regarding their ability to inhibit maitotoxin-elicited Ca2+ influx in rat C6 glioma cells. © 2014 American Chemical Society;
D O I
暂无
中图分类号
学科分类号
摘要
Journal article (JA)
引用
收藏
相关论文
共 50 条
  • [41] Synthesis and biological evaluation of cytostatin analogues
    Bialy, L
    Waldmann, H
    CHEMICAL COMMUNICATIONS, 2003, (15) : 1872 - 1873
  • [42] Synthesis and biological evaluation of gambierol analogues
    Fuwa, H
    Kainuma, N
    Satake, M
    Sasaki, M
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) : 2519 - 2522
  • [43] Synthesis and Biological Evaluation of Curcuminoid Derivatives
    Feng, Ling
    Li, Yang
    Song, Zhi-fang
    Li, Hui-jing
    Huai, Qi-yong
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2015, 63 (11) : 873 - 881
  • [44] SYNTHESIS AND BIOLOGICAL EVALUATION OF MODIFIED TAXOLS
    JITRANGSRI, C
    KINGSTON, DGI
    MAGRI, NF
    HORWITZ, S
    MELLADO, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 188 (AUG): : 118 - MEDI
  • [45] SYNTHESIS AND BIOLOGICAL EVALUATION OF POTENTIAL IMMUNOMODULATORS
    PHILLIPS, NC
    STILLINGS, MR
    INTERNATIONAL JOURNAL OF IMMUNOPHARMACOLOGY, 1980, 2 (03): : 203 - 204
  • [46] Synthesis and biological evaluation of fluorinated acyclothionucleosides
    Gouault-Bironneau, Sonia
    Sene, Aboubacary
    Catel, Jean-Marie
    Lequeux, Thierry
    JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (09) : 848 - 851
  • [47] Synthesis and biological evaluation of new thiazolopyrimidines
    Said, M
    Abouzid, K
    Mouneer, A
    Ahmedy, A
    Osman, AM
    ARCHIVES OF PHARMACAL RESEARCH, 2004, 27 (05) : 471 - 477
  • [48] Synthesis and Biological Evaluation of Neopeltolide and Analogs
    Cui, Yubo
    Balachandran, Raghavan
    Day, Billy W.
    Floreancig, Paul E.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (05): : 2225 - 2235
  • [49] SYNTHESIS AND IN VITRO BIOLOGICAL EVALUATION OF CANANODINE
    Yusuf, Abdullah
    Aibibula, Paruke
    Zhang, Ju-Bao
    Huang, Guo-Zheng
    Aisa, Haji Akber
    Zhao, Jiang-Yu
    HETEROCYCLES, 2021, 102 (03) : 506 - 515
  • [50] Synthesis and Biological Evaluation of Bisthiazoles and Polythiazoles
    Al-Omair, Mohammed A.
    Sayed, Abdelwahed R.
    Youssef, Magdy M.
    MOLECULES, 2018, 23 (05):