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
  • [1] Design, synthesis, and in vitro biological evaluation of (+)-discodermolide analogues.
    Xian, M
    LaMarche, MJ
    Hirose, T
    Freeze, BS
    Smith, AB
    Burlingame, MA
    Shaw, SJ
    Sundermann, KF
    Zhang, D
    Petryka, J
    Mendoza, E
    Liu, FH
    Myles, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U81 - U81
  • [2] Design, synthesis, and biological evaluation of novel metabolically stable (+)-discodermolide analogues
    Guo, Boying
    Zhang, Nan
    McDaid, Hayley
    Horwitz, Susan
    Smith, Amos
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [3] Design, synthesis and cytotoxicity of discodermolide analogues.
    Burlingame, MA
    Shaw, SJ
    Sundermann, KF
    Zhang, D
    Petryka, J
    Mendoza, E
    Liu, FH
    Myles, DC
    LaMarche, MJ
    Hirose, T
    Freeze, BS
    Smith, AB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U183 - U183
  • [4] Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
    Preet Anand
    Baldev Singh
    Medicinal Chemistry Research, 2013, 22 : 1648 - 1659
  • [5] Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
    Anand, Preet
    Singh, Baldev
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) : 1648 - 1659
  • [6] Conception, Synthesis, and Biological Evaluation of Original Discodermolide Analogues
    de Lemos, Elsa
    Agouridas, Evangelos
    Sorin, Geoffroy
    Guerreiro, Antonio
    Commercon, Alain
    Pancrazi, Ange
    Betzer, Jean-Francois
    Lannou, Marie-Isabelle
    Ardisson, Janick
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (36) : 10123 - 10134
  • [7] Design, total synthesis, and evaluation of C(13)-C(14) cyclopropane analogues of (+)-discodermolide
    Smith, AB
    Xian, M
    Liu, FH
    ORGANIC LETTERS, 2005, 7 (21) : 4613 - 4616
  • [8] (+)-discodermolide: total synthesis, construction of novel analogues, and biological evaluation
    Smith, Amos B., III
    Freeze, B. Scott
    TETRAHEDRON, 2008, 64 (02) : 261 - 298
  • [9] Synthesis, anticholinesterase activity and molecular modeling study of novel carbamate-substituted thymol/carvacrol derivatives
    Kurt, Belma Zengin
    Gazioglu, Isil
    Dag, Aydan
    Salmas, Ramin Ekhteiari
    Kayik, Gulru
    Durdagi, Serdar
    Sonmez, Fatih
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (04) : 1352 - 1363
  • [10] Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues
    Burlingame, MA
    Shaw, SJ
    Sundermann, KF
    Zhang, D
    Petryka, J
    Mendoza, E
    Liu, FH
    Myles, DC
    LaMarche, MJ
    Hirose, T
    Freeze, BS
    Smith, AB
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) : 2335 - 2338