Preliminary structure-antiangiogenic activity relationships of 4-senecioyloxymethyl-6,7-dimethoxycoumarin

被引：34
作者：
Nam, NH
Kim, Y
You, YJ
Hong, DH
Kim, HM
Ahn, BZ [1 ]
机构：
[1] Chungnam Natl Univ, Coll Pharm, Taejon 305764, South Korea
[2] Res Inst Biosci & Biotechnol, Taejon 305600, South Korea
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 17期
关键词：
D O I：
10.1016/S0960-894X(02)00392-X
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain with various cinnamoyl groups we discovered 6d, bearing a 4-methoxycinnamoyl instead of senecioyl side chain, with inhibitory activity in HUVEC tube formation assay enhanced by one order of magnitude compared to 1. We have also synthesized compound 12, an analogue of 6d, with equipotency and improved water solubility. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2345 / 2348
页数：4
相关论文
共 31 条
[1]   A novel synthesis of heterocyclic compounds containing coumarin moiety of potential antimicrobial activity [J].
Abd El-Fattah, ME .
ARCHIVES OF PHARMACAL RESEARCH, 1998, 21 (06) :723-728
[2]   Constituents and cytotoxicity of Zanthoxylum rhesta stem bark [J].
Ahsan, M ;
Zaman, TA ;
Hasan, BM ;
Ito, C ;
Islam, SKN .
FITOTERAPIA, 2000, 71 (06) :697-700
[3]  
ASHIMIRO N, 1999, MED CHEM, V42, P669
[4]   SYNTHESIS AND CYTOSTATIC ACTIVITY OF GEIPARVARIN ANALOGS [J].
BARALDI, PG ;
GUARNERI, M ;
MANFREDINI, S ;
SIMONI, D ;
BALZARINI, J ;
DECLERCQ, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :284-288
[5]   GEIPARVARIN ANALOGS .3. SYNTHESIS AND CYTOSTATIC ACTIVITY OF 3(2H)-FURANONE AND 4,5-DIHYDRO-3(2H)-FURANONE CONGENERS OF GEIPARVARIN, CONTAINING A GERANIOL-LIKE FRAGMENT IN THE SIDE-CHAIN [J].
BARALDI, PG ;
MANFREDINI, S ;
SIMONI, D ;
TABRIZI, MA ;
BALZARINI, J ;
DECLERCQ, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (10) :1877-1882
[6]   PM-94128, a new isocoumarin antitumor agent produced by a marine bacterium [J].
Canedo, LM ;
Puentes, JLF ;
Baz, JP .
JOURNAL OF ANTIBIOTICS, 1997, 50 (02) :175-176
[7]  
DEJARDIN JV, 1983, ANN PHARM FR, V41, P437
[8]   Studies on the cytostatic and cytotoxic effects and mode of action of 8-nitro-7-hydroxycoumarin [J].
Egan, D ;
James, P ;
Cooke, D ;
OKennedy, R .
CANCER LETTERS, 1997, 118 (02) :201-211
[9]   SYNTHESIS OF NEW 7-SUBSTITUTED 4-METHYLCOUMARIN DERIVATIVES OF ANTIMICROBIAL ACTIVITY [J].
EID, AI ;
RAGAB, FA ;
ELANSARY, SL ;
ELGAZAYERLY, SM ;
MOURAD, FE .
ARCHIV DER PHARMAZIE, 1994, 327 (04) :211-213
[10]   Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers [J].
Flavin, MT ;
Rizzo, JD ;
Khilevich, A ;
Kucherenko, A ;
Sheinkman, AK ;
Vilaychack, V ;
Lin, L ;
Chen, W ;
Greenwood, EM ;
Pengsuparp, T ;
Pezzuto, JM ;
Hughes, SH ;
Flavin, TM ;
Cibulski, M ;
Boulanger, WA ;
Shone, RL ;
Xu, ZQ .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (06) :1303-1313
1234