Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

被引:42
|
作者
Smith, AB
Freeze, BS
LaMarche, MJ
Hirose, T
Brouard, I
Rucker, PV
Xian, M
Sundermann, KF
Shaw, SJ
Burlingame, MA
Horwitz, SB
Myles, DC [1 ]
机构
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
[2] Kosan Biosci Inc, Hayward, CA 94545 USA
[3] Albert Einstein Coll Med, Dept Mol Pharmacol, Bronx, NY 10461 USA
关键词
D O I
10.1021/ol047686a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule-stabilizing agent (divided by)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined. exploiting two synthetically simplified scaffolds. as well as the parent (+)-discodermolide framework.
引用
收藏
页码:311 / 314
页数:4
相关论文
共 50 条
  • [41] Design, synthesis and antibacterial evaluation of novel AHL analogues
    Ren, Jing-Li
    Zhang, En
    Ye, Xian-Wei
    Wang, Meng-Meng
    Yu, Bin
    Wang, Wen-Hua
    Guo, Ya-Zhuo
    Liu, Hong-Min
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (14) : 4154 - 4156
  • [42] Synthesis and Evaluation of S- and C(1)-Substituted Analogues of Lincomycin
    Collin, Marie-Pierre
    Hobbie, Sven N.
    Boettger, Erik C.
    Vasella, Andrea
    HELVETICA CHIMICA ACTA, 2009, 92 (02) : 230 - 266
  • [43] Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues
    Wang, Baozhu
    Cheng, Jiagao
    Xu, Zhiping
    Xu, Xiaoyong
    Shao, Xusheng
    Li, Zhong
    MOLECULES, 2012, 17 (09) : 10014 - 10025
  • [44] Synthesis and biological evaluation of two novel 2′-substituted tiazofurin analogues
    Popsavin, M
    Torovic, L
    Kojic, V
    Bogdanovic, G
    Popsavin, V
    TETRAHEDRON LETTERS, 2004, 45 (38) : 7125 - 7128
  • [45] Design, Synthesis and Evaluation of Fluorescent Analogues of Abscisic Acid
    Gonzalez, Florenci, V
    Bou-Iserte, Lledo
    Miguel-Lopez, Borja
    de la Hoz-Rodriguez, Sergio
    Kersten, Christian
    Sanchez-Sarasua, Sandra
    Espinosa-Fernandez, Veronica
    Maria Sanchez-Perez, Ana
    CHEMISTRYSELECT, 2020, 5 (26): : 8015 - 8019
  • [46] Design, synthesis, and biological evaluation of thiophene analogues of chalcones
    Romagnoli, Romeo
    Baraldi, Pier Giovanni
    Carrion, Maria Dora
    Cara, Carlota Lopez
    Cruz-Lopez, Olga
    Preti, Delia
    Tolomeo, Manlio
    Grimaudo, Stefania
    Di Cristina, Antonella
    Zonta, Nicola
    Balzarini, Jan
    Brancale, Andrea
    Sarkar, Taradas
    Hamel, Ernest
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (10) : 5367 - 5376
  • [47] Design, synthesis, and bioactivity evaluation of antitumor sorafenib analogues
    Zhou, Shiyang
    Chen, Guangying
    RSC ADVANCES, 2018, 8 (66): : 37643 - 37651
  • [48] Design, synthesis and evaluation of a series of novel fumagillin analogues
    Fardis, M
    Pyun, HJ
    Tario, J
    Jin, HL
    Kim, CU
    Ruckman, J
    Lin, Y
    Green, L
    Hicke, B
    BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) : 5051 - 5058
  • [49] Design, synthesis and evaluation of serine protease inhibitor analogues
    Kamoune, Laila
    De Borggraeve, Wim M.
    Gielens, Constant
    Voet, Arnout
    Robeyns, Koen
    De Maeyer, Marc
    Van Meervelt, Luc
    Compernolle, Frans
    Hoornaert, Georges
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (18) : 2977 - 2986
  • [50] Synthesis and Biological Evaluation of Novel Substituted Pyrrolyl and Pyrazolyl Oxazolidinone Analogues
    Kwon, Jin-Sun
    Hong, Chang-Sung
    Jung, Ju-Young
    Yu, Seung-Woo
    Ryu, Jung-Su
    Kim, Young-Jae
    Yoon, Jong-Min
    Lee, Hong-Sub
    Kang, Jae-Hoon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (08): : 1895 - 1898