Deletion of the oxetane ring in docetaxel analogues:: Synthesis and biological evaluation

被引:13
|
作者
Deka, V [1 ]
Dubois, J [1 ]
Thoret, S [1 ]
Guéritte, F [1 ]
Guénard, D [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1021/ol036043c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Two new docetaxel analogues have been prepared starting from 10-deacetylbaccatin III. Both derivatives lack the oxetane D-ring but possess the 4alpha-acetoxy group, which is important for biological activity. The influence of a more or less constrained C-ring was evaluated by adding, or not adding, a double bond in this ring. Both compounds were found to be equally less active than docetaxel in biological assays.
引用
收藏
页码:5031 / 5034
页数:4
相关论文
共 50 条
  • [21] Synthesis and biological evaluation of gambierol analogues
    Fuwa, H
    Kainuma, N
    Satake, M
    Sasaki, M
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) : 2519 - 2522
  • [22] Synthesis and biological evaluation of spirastrellolide A analogues
    Manda, Jagadeesh Nagendra
    Butler, Barry
    Aponick, Aaron
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [23] Synthesis and biological evaluation of apicularen A analogues
    Petri, AF
    Sasse, F
    Maier, ME
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (09) : 1865 - 1875
  • [24] Synthesis and biological evaluation of cruentaren A analogues
    Vintonyak, Viktor V.
    Cala, Marcellino
    Lay, Frank
    Kunze, Brigitte
    Sasse, Florenz
    Maiera, Martin E.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) : 3709 - 3720
  • [25] Synthesis and Biological Evaluation of Isofebrifugine Analogues
    Zhang, Jinjin
    Huang, Baohua
    Lu, Yujing
    Li, Wenbin
    Zhuang, Zichong
    Ke, Donghua
    Zhong, Jingpeng
    Zhou, Jinlin
    Chen, Qian
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (12) : 1004 - 1010
  • [26] Synthesis, Biological Evaluation and Docking Studies of Ring-Opened Analogues of Ipomoeassin F
    O'Keefe, Sarah
    Bhadra, Pratiti
    Duah, Kwabena B.
    Zong, Guanghui
    Tenay, Levise
    Andrews, Lauren
    Schneider, Hayden
    Anderson, Ashley
    Hu, Zhijian
    Aljewari, Hazim S.
    Hall, Belinda S.
    Simmonds, Rachel E.
    Helms, Volkhard
    High, Stephen
    Shi, Wei Q.
    MOLECULES, 2022, 27 (14):
  • [27] Toward "E-Ring-Free" Lamellarin Analogues: Synthesis and Preliminary Biological Evaluation
    Rusanov, Daniil A.
    Alfadul, Samah Mutasim
    Portnyagina, Ekaterina Yu.
    Silyanova, Eugenia A.
    Kuznetsov, Nikita A.
    Podpovetny, Kirill E.
    Samet, Alexander V.
    Semenov, Victor V.
    Babak, Maria V.
    CHEMBIOCHEM, 2023, 24 (11)
  • [28] Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogues
    Gunatilaka, AAL
    Ramdayal, FD
    Sarragiotto, MH
    Kingston, DGI
    Sackett, DL
    Hamel, E
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08): : 2694 - 2703
  • [29] Synthesis and biological evaluation of simplified pironetin analogues with modifications in the side chain and the lactone ring
    Roldan, Steven
    Cardona, Adria
    Conesa, Laura
    Murga, Juan
    Falomir, Eva
    Carda, Miguel
    Alberto Marco, J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (01) : 220 - 232
  • [30] A novel D-ring modified taxoid: synthesis and biological evaluation of a γ-lactone analogue of docetaxel
    Gao, Feng
    Yang, Zhan-Kun
    Chen, Qiao-Hong
    Chen, Xiao-Guang
    Wang, Feng-Peng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (02) : 361 - 366