Synthesis of 5(20)deoxydocetaxel, a new active docetaxel analogue

被引:33
作者
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
taxoids; docetaxel; oxetane; 10-deacetyl baccatin III; microtubules;
D O I
10.1016/S0040-4039(00)00379-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5(20)Deoxydocetaxel was prepared from 13-oxo-10-deacetyl baccatin III. This compound is the first docetaxel analogue with a modified D-ring which is as active as paclitaxel on microtubules. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3331 / 3334
页数:4
相关论文
共 18 条
[1]   SYNTHESIS OF A FUNCTIONALIZED BIS-SPIROACETAL [J].
BRIMBLE, MA ;
WILLIAMS, GM ;
BAKER, R ;
JAMES, M .
TETRAHEDRON LETTERS, 1990, 31 (21) :3043-3046
[2]   2-MONOSUBSTITUTED-1,3-OXAZOLIDINES AS IMPROVED PROTECTIVE GROUPS OF N-BOC-PHENYLISOSERINE IN DOCETAXEL PREPARATION [J].
DIDIER, E ;
FOUQUE, E ;
TAILLEPIED, I ;
COMMERCON, A .
TETRAHEDRON LETTERS, 1994, 35 (15) :2349-2352
[3]  
FARINA V, 1995, CHEM PHARM TAXOL ITS
[4]   Synthesis of azetidine-type taxanes [J].
Fenoglio, I ;
Nano, GM ;
VanderVelde, DG ;
Appendino, G .
TETRAHEDRON LETTERS, 1996, 37 (18) :3203-3206
[5]  
GEORG I, 1995, ACS S SERIES, V583
[6]   TAXOL AND TAXOTERE - DISCOVERY, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
GUENARD, D ;
GUERITTEVOEGELEIN, F ;
POTIER, P .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :160-167
[7]  
Guenard D., 1995, CURRENT PHARM DESIGN, V1, P95
[8]   Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogues [J].
Gunatilaka, AAL ;
Ramdayal, FD ;
Sarragiotto, MH ;
Kingston, DGI ;
Sackett, DL ;
Hamel, E .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2694-2703
[9]   EPOXIDATIONS WITH TRIPHENYLPHOSPHINE AND DIETHYL AZODICARBOXYLATE .1. SYNTHESIS OF METHYL 3,4-ANHYDRO-D-TAGATOFURANOSIDES [J].
GUTHRIE, RD ;
JENKINS, ID ;
YAMASAKI, R ;
SKELTON, BW ;
WHITE, AH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08) :2328-2334
[10]   RELATIONSHIPS BETWEEN THE STRUCTURES OF TAXOL AND BACCATINE-III DERIVATIVES AND THEIR INVITRO ACTION ON THE DISASSEMBLY OF MAMMALIAN BRAIN AND PHYSARUM AMEBAL MICROTUBULES [J].
LATASTE, H ;
SENILH, V ;
WRIGHT, M ;
GUENARD, D ;
POTIER, P .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1984, 81 (13) :4090-4094