Synthesis and cytotoxic evaluation of a series of genistein derivatives

被引:33
作者
Li, HQ [1 ]
Ge, HM [1 ]
Chen, YX [1 ]
Xu, C [1 ]
Shi, L [1 ]
Ding, H [1 ]
Zhu, HL [1 ]
Tan, RX [1 ]
机构
[1] Nanjing Univ, Inst Funct Biomol, State Key Lab Pharmaceut Biotechnol, Nanjing 210093, Peoples R China
关键词
D O I
10.1002/cbdv.200690049
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Thirty genistein (= 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one: GEN) derivatives were synthesized from genistein through a facile approach in high yields, Compounds 9. 11 12, 23-30 were reported for the first time, while 13-22 have already been reported in our recent paper. The cytotoxic activities of these compounds were evaluated against a human nasopharyngeal epidermoid tumor cell line KB. Compounds 7-9, 12, 14, 16-19, 21, 24, 27, 29 showed remarkable antitumor activities in vitro, which was comparable with 5-fluorouracil, an anticancer drug. On the basis of the obtained experimental data, structure-effect relationships were discussed.
引用
收藏
页码:463 / 472
页数:10
相关论文
共 15 条
[1]   Effect of natural and synthetic estrogens on A549 lung cancer cells: Correlation of chemical structures with cytotoxic effects [J].
Andreescu, S ;
Sadik, OA ;
McGee, DW .
CHEMICAL RESEARCH IN TOXICOLOGY, 2005, 18 (03) :466-474
[2]   Autonomous multielectrode system for monitoring the interactions of isoflavonoids with lung cancer cells [J].
Andreescu, S ;
Sadik, OA ;
McGee, DW .
ANALYTICAL CHEMISTRY, 2004, 76 (08) :2321-2330
[3]   Synthesis and biological evaluation of dimeric RGD peptide-paclitaxel conjugate as a model for integrin-targeted drug delivery [J].
Chen, XY ;
Plasencia, C ;
Hou, YP ;
Neamati, N .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (04) :1098-1106
[4]  
Delcanale M, 2001, HELV CHIM ACTA, V84, P2417, DOI 10.1002/1522-2675(20010815)84:8<2417::AID-HLCA2417>3.0.CO
[5]  
2-N
[6]   The synthesis of daidzein sulfates [J].
Fairley, B ;
Botting, NP ;
Cassidy, A .
TETRAHEDRON, 2003, 59 (29) :5407-5410
[7]   ISOFLAVONE SYNTHESIS WITH 1,3,5-TRIAZINE [J].
JHA, HC ;
ZILLIKEN, F ;
BREITMAIER, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (01) :102-103
[8]   Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones [J].
Kim, YW ;
Hackett, JC ;
Brueggemeier, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (16) :4032-4040
[9]   The phase transfer catalysed synthesis of isoflavone-O-glucosides [J].
Lewis, P ;
Kaltia, S ;
Wähälä, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16) :2481-2484
[10]   Identification of a signaling cascade for interleukin-8 production by Helicobacter pylori in human gastric epithelial cells [J].
Nozawa, Y ;
Nishihara, K ;
Peek, RM ;
Nakano, M ;
Uji, T ;
Ajioka, H ;
Matsuura, N ;
Miyake, H .
BIOCHEMICAL PHARMACOLOGY, 2002, 64 (01) :21-30