Design, synthesis and biological evaluation of bridged epothilone D analogues

被引：13

作者：

Chen, Qiao-Hong ^{[1
]}

Ganesh, Thota ^{[1
,2
]}

Brodie, Peggy ^{[1
]}

Slebodnick, Carla ^{[1
]}

Jiang, Yi ^{[3
]}

Banerjee, Abhijit ^{[2
]}

Bane, Susan ^{[3
]}

Snyder, James P. ^{[2
]}

Kingston, David G. I. ^{[1
]}

机构：

[1] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA

[2] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

[3] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 24期

关键词：

D O I：

10.1039/b814823f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Six epothilone D analogues with a bridge between the C4-methyl and the C12-methyl carbons were prepared in an attempt to constrain epothilone D to its proposed tubulin-binding conformation. Ring-closing metathesis (RCM) was employed as the key step to build the C4-C26 bridge. In antiproliferative assays in the human ovarian cancer (A2780) and prostate cancer (PC3) cell lines, and also in tubulin assembly assay, all these compounds proved to be less active than epothilone D.

引用

页码：4542 / 4552

页数：11

共 50 条

[41] Design, synthesis and biological evaluation of sulfenimine cephalosporin analogues as β-lactamase inhibitors
Kai Zhang
Huaiwei Ding
Ailong Shi
Qi Huang
Hongrui Song
Decai Fu
Chemical Research in Chinese Universities, 2015, 31 : 388 - 393
[42] Design, synthesis, and biological evaluation of the analogues of glaziovianin A, a potent antitumor isoflavone
Hayakawa, Ichiro
Ikedo, Akiyuki
Chinen, Takumi
Usui, Takeo
Kigoshi, Hideo
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (19) : 5745 - 5756
[43] Design, synthesis, and biological properties of highly potent tubulysin D analogues
Patterson, Andrew W.
Peltier, Hillary M.
Sasse, Florenz
Ellman, Jonathan A.
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (34) : 9534 - 9541
[44] Design, synthesis and biological evaluation of novel etoposide analogues as cytotoxic agents
Liu Ying-Qian
Yang Hua
Tian Xuan
CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (06) : 785 - 790
[45] Design, Synthesis and Biological Evaluation of Sulfenimine Cephalosporin Analogues as β-Lactamase Inhibitors
Zhang Kai
Ding Huaiwei
Shi Ailong
Huang Qi
Song Hongrui
Fu Decai
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2015, 31 (03) : 388 - 393
[46] 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
[47] Design, Synthesis, and Biological Evaluation of Ring-Opened Bengamide Analogues
Tai, Wan-Yi
Zhang, Run-Tao
Ma, Yi-Ming
Gu, Min
Liu, Gang
Li, Jia
Nan, Fa-Jun
CHEMMEDCHEM, 2011, 6 (09) : 1555 - 1558
[48] Novel promising linezolid analogues: Rational design, synthesis and biological evaluation
De Rosa, Margherita
Zanfardino, Anna
Notomista, Eugenio
Wichelhaus, Thomas A.
Saturnino, Carmela
Varcamonti, Mario
Soriente, Annunziata
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 : 779 - 785
[49] Design and synthesis of bridged γ-lactams as analogues of β-lactam antibiotics
Aszodi, J
Rowlands, DA
Mauvais, P
Collette, P
Bonnefoy, A
Lampilas, M
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (10) : 2489 - 2492
[50] Synthesis and biological evaluation of highly potent analogues of epothilones B and D
Altmann, KH
Bold, G
Caravatti, G
Flörsheimer, A
Guagnano, V
Wartmann, M
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (24) : 2765 - 2768

← 1 2 3 4 5 →