Synthesis of paclitaxel (Docetaxel)/2-deacetoxytaxinine J dimers

被引：9
作者：
Appendino, G
Belloro, E
Jakupovic, S
Danieli, B
Jakupovic, J
Bombardelli, E
机构：
[1] Dipartimento Sci & Tecnol Farm, I-10125 Turin, Italy
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[3] Tech Univ Berlin, Inst Organ Chem, D-10623 Berlin, Germany
[4] Indena SpA, I-20141 Milan, Italy
来源：
TETRAHEDRON | 1999年 / 55卷 / 21期
关键词：
taxoids; dimers; antitumour compounds;
D O I：
10.1016/S0040-4020(99)00290-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Starting from taxanes available in multigram amounts from widespread ornamental yews (10-deacetylbaccatin III (4) and 2'-deacetoxyaustrospicatine (5)), two dimeric taxoids (3a, 3b) with potential dual target specificity (beta-tubulin and P-gp) were synthesised. Both compounds lacked significant cytotoxicity, though 3b retained a strong activity in the tubulin depolimerisation assay. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6567 / 6576
页数：10
相关论文
共 37 条
[1]  
ALL SM, 1995, J MED CHEM, V38, P2821
[2]   Effects of yew alkaloids and related compounds on guinea-pig isolated perfused heart and papillary muscle [J].
Alloatti, G ;
Penna, C ;
Levi, RC ;
Gallo, MP ;
Appendino, G ;
Fenoglio, I .
LIFE SCIENCES, 1996, 58 (10) :845-854
[3]   THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES .14. TAXOIDS FROM THE ROOTS OF TAXUS X MEDIA CV HICKSII [J].
APPENDINO, G ;
CRAVOTTO, G ;
ENRIU, R ;
GARIBOLDI, P ;
BARBONI, L ;
TORREGIANI, E ;
GABETTA, B ;
ZINI, G ;
BOMBARDELLI, E .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (05) :607-613
[4]   Synthesis of a conformationally restricted analogue of paclitaxel [J].
Barboni, L ;
Lambertucci, C ;
Ballini, R ;
Appendino, G ;
Bombardelli, E .
TETRAHEDRON LETTERS, 1998, 39 (39) :7177-7180
[5]   SYNTHETIC STUDIES TOWARDS TAXOL ANALOGS - CHEMOSELECTIVE CLEAVAGE OF C-5 CINNAMOYL GROUP IN TAXANE GROUP OF DITERPENOIDS WITH HYDROXYLAMINE [J].
BATHINI, Y ;
MICETICH, RG ;
DANESHTALAB, M .
SYNTHETIC COMMUNICATIONS, 1994, 24 (11) :1513-1517
[6]  
Bourguignon JJ, 1996, PRACTICE MED CHEM, P261
[7]   A TAXANE FROM THE HIMALAYAN YEW, TAXUS-WALLICHIANA [J].
CHATTOPADHYAY, SK ;
SHARMA, RP .
PHYTOCHEMISTRY, 1995, 39 (04) :935-936
[8]  
CHEN SH, 1995, CHEM PHARM TAXOL ITS, P165
[9]   INTERNAL NUCLEOPHILE ASSISTED SELECTIVE DEESTERIFICATION STUDIES ON BACCATIN-III - SYNTHESIS OF 2-DEBENZOYLBACCATIN-III AND 4-DEACETYLBACCATIN-III ANALOGS [J].
DATTA, A ;
JAYASINGHE, LR ;
GEORG, GI .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4689-4690
[10]   A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL [J].
DENIS, JN ;
GREENE, AE ;
GUENARD, D ;
GUERITTEVOEGELEIN, F ;
MANGATAL, L ;
POTIER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5917-5919
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