New C(4)-functionalized colchicine derivatives by a versatile multicomponent electrophilic aromatic substitution

被引:8
作者
Bensel, N
Lagnoux, D
Niggli, V
Wartmann, M
Reymond, JL
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
[2] Univ Bern, Inst Pathol, CH-3010 Bern, Switzerland
[3] Novartis Inst Biomed Res, CH-4002 Basel, Switzerland
[4] Novartis Inst Oncol Res, CH-4002 Basel, Switzerland
关键词
D O I
10.1002/hlca.200490203
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electrophilic alkylation of colchicine at C(4) was accomplished by a multicomponent aromatic electrophilic substitution reaction with electrophilic aldehydes and carboxylic acids or amides in H2SO4. A series of new derivatives were obtained and evaluated for their antiproliferative effect towards various tumor cell lines, and their stimulatory effect on the development of polarity in human neutrophils.
引用
收藏
页码:2266 / 2272
页数:7
相关论文
共 17 条
[1]  
Agababyan A.G., 1982, RUSS CHEM REV, V51, P387
[2]   ISOLATION AND GENETIC-CHARACTERIZATION OF HUMAN KB-CELL LINES RESISTANT TO MULTIPLE-DRUGS [J].
AKIYAMA, SI ;
FOJO, A ;
HANOVER, JA ;
PASTAN, I ;
GOTTESMAN, MM .
SOMATIC CELL AND MOLECULAR GENETICS, 1985, 11 (02) :117-126
[3]   Straightforward synthesis of N-protected benzylic amines by carbamoalkylation of aromatic compounds [J].
Bensel, N ;
Pevere, V ;
Desmurs, JR ;
Wagner, A ;
Mioskowski, C .
TETRAHEDRON LETTERS, 1999, 40 (05) :879-882
[4]  
FOJO A, 1985, CANCER RES, V45, P3002
[5]   Total syntheses of colchicine in comparison: A journey through 50 years of synthetic organic chemistry [J].
Graening, T ;
Schmalz, HG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3230-3256
[6]   Differentiated HL-60 cells are a valid model system for the analysis of human neutrophil migration and chemotaxis [J].
Hauert, AB ;
Martinelli, S ;
Marone, C ;
Niggli, V .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 2002, 34 (07) :838-854
[7]   Synthesis of 4-acetylcolchicine [J].
Kouroupis, P ;
Linden, A ;
Hansen, HJ .
HELVETICA CHIMICA ACTA, 1996, 79 (01) :203-207
[8]   FROM COLCHICINE AND SOME OF ITS DERIVATIVES TO 1,2,3,9,10-PENTAMETHOXYBENZO[A]HEPTALENES [J].
KOUROUPIS, P ;
HANSEN, HJ .
HELVETICA CHIMICA ACTA, 1995, 78 (05) :1247-1277
[9]  
LEVY F, 1971, MEM SOC BOT, V145, P554
[10]   A convenient tubulin-based quantitative assay for paclitaxel (Taxol) derivatives more effective in inducing assembly than the parent compound [J].
Lin, CM ;
Jiang, YQ ;
Chaudhary, AG ;
Rimoldi, JM ;
Kingston, DGI ;
Hamel, E .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1996, 38 (02) :136-140