Synthesis and biological activity of mycalolide analogs

被引:28
|
作者
Suenaga, Kiyotake [1 ]
Kimura, Tomoyuki [1 ]
Kuroda, Takeshi [1 ]
Matsui, Keita [1 ]
Miya, Saori [1 ]
Kuribayashi, Satomi [1 ]
Sakakura, Akira [1 ]
Kigoshi, Hideo [1 ]
机构
[1] Univ Tsukuba, Dept Chem, Tsukuba, Ibaraki 3058571, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/j.tet.2006.06.046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mycalolide analog 4, consisting only of the side chain of mycalolide B (2), a trisoxazole macrolide of marine origin, was stereoselectively synthesized using Roush crotylboration, an Evans aldol reaction, and a Paterson aldol reaction as key steps. The analog 4 was found to have strong actin-depolymerizing activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8278 / 8290
页数:13
相关论文
共 50 条
  • [41] Design, Synthesis, and Biological Evaluations of Aplyronine A-Mycalolide B Hybrid Compound
    Kobayashi, Kenichi
    Fujii, Yusuke
    Hirayama, Yuichiro
    Kobayashi, Shinichi
    Hayakawa, Ichiro
    Kigoshi, Hideo
    ORGANIC LETTERS, 2012, 14 (05) : 1290 - 1293
  • [42] Synthesis and biological activity of photostable and persistent abscisic acid analogs
    Takeuchi, Jun
    Asakura, Haruka
    Ozasa, Yuri
    Koide, Motoki
    Ohnishi, Toshiyuki
    Todoroki, Yasushi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (48) : 9616 - 9622
  • [43] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SULFIDE AND SULFONIUM ANALOGS OF SULPIRIDE
    HARROLD, MW
    WALLACE, RA
    FAROOQUI, T
    URETSKY, N
    MILLER, DD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 108 - MEDI
  • [44] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF THE METHYLTHIO ANALOGS OF FLUOXETINE AND SEPROXETINE
    KRUSHINSKI, JH
    ROBERTSON, DW
    MAYLE, DA
    WONG, DT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 162 - MEDI
  • [45] Synthesis and biological activity of glycolipids, with a focus on gangliosides and sulfatide analogs
    Ikami, T
    Ishida, H
    Kiso, M
    SPHINGOLIPID METABOLISM AND CELL SIGNALING, PT A, 2000, 311 : 547 - 568
  • [46] Design, synthesis and biological activity of peptidomimetic analogs of insect allatostatins
    Xie, Yong
    Kai, Zhen Peng
    Tobe, Stephen S.
    Deng, Xi Le
    Ling, Yun
    Wu, Xiao Qin
    Huang, Juan
    Zhang, Li
    Yang, Xin Ling
    PEPTIDES, 2011, 32 (03) : 581 - 586
  • [47] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF MERCAPTOTHIOLCARBOXYLIC ACIDS AND THEIR CYCLIC ANALOGS
    LISINA, NI
    VASILEVA, TP
    BYSTROVA, VM
    KILDISHEVA, OV
    CHERNOV, GA
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1987, 21 (02): : 177 - 181
  • [48] New analogs of antiherpes virus drugs - synthesis and biological activity
    Stankova, I. G.
    Dzimbova, T. A.
    Shishkov, S. A.
    Kostova, K. A.
    Galabov, A. S.
    AMINO ACIDS, 2007, 33 (03) : XVII - XVII
  • [49] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF BETA-MELANOTROPINS AND ANALOGS
    LEMAIRE, S
    YAMASHIRO, D
    RAO, AJ
    LI, CH
    JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (01) : 155 - 158
  • [50] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ANALOGS OF FECAPENTAENE-12
    GOVINDAN, SV
    KINGSTON, DGI
    GUNATILAKA, AAL
    VANTASSELL, RL
    WILKINS, TD
    DEWIT, PP
    VANDERSTEEG, M
    VANDERGEN, A
    JOURNAL OF NATURAL PRODUCTS, 1987, 50 (01): : 75 - 83