6-Substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives in a new approach of the treatment of cancer cell invasion and metastasis

被引:53
作者
Kempen, Isabelle [1 ]
Hemmer, Marc [1 ]
Counerotte, Stephane [1 ]
Pochet, Lionel [2 ]
de Tullio, Pascal [1 ]
Foidart, Jean-Michel [3 ]
Blacher, Silvia [3 ]
Noel, Agnes [3 ]
Frankenne, Francis [3 ]
Pirotte, Bernard [1 ]
机构
[1] Univ Liege, Lab Chim Pharmaceut, Drug Res Ctr, B-4000 Liege, Belgium
[2] Univ Namur, Dept Pharm, FUNDP, B-5000 Namur, Belgium
[3] Univ Liege, Lab Biol Tumeurs & Dev, B-4000 Liege, Belgium
关键词
Coumarin derivatives; Cancer; Cell invasion; Anti-cancer drug;
D O I
10.1016/j.ejmech.2008.01.024
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel 6-substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives were synthesized and their potency in reducing the invasive behaviour of HT 1080 fibrosarcoma cells was evaluated. Structure-activity relationships were deduced from biological results and will be used in further design of new active compounds. In particular, the acetoxymethyl substituent found at the 6-position of previously described active compounds can be replaced by an acetamidomethyl substituent without loss of potency; while the presence of an aryl ester function at the 3-position was preferred to a thioester or an amide function to induce marked biological activity. This work confirms the interest of aryl esters of 6-substituted coumarin-3-carboxylic acids as potential new anti-cancer agents. (C) 2008 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:2735 / 2750
页数:16
相关论文
共 24 条
[1]   Targeting angiogenesis for the treatment of sarcoma [J].
Balasubramanian, Lakshmi ;
Evens, Andrew M. .
CURRENT OPINION IN ONCOLOGY, 2006, 18 (04) :354-359
[2]   Sunitinib: A newly approved small-molecule inhibitor of angiogenesis [J].
Cabebe, Elwyn ;
Wakelee, Heather .
DRUGS OF TODAY, 2006, 42 (06) :387-398
[3]   Antiangiogenic drugs in non-small cell lung cancer treatment [J].
Cascone, T ;
Troiani, T ;
Morelli, MP ;
Gridelli, C ;
Ciardiello, F .
CURRENT OPINION IN ONCOLOGY, 2006, 18 (02) :151-155
[4]   An improved synthesis of the selective matrix metal metalloproteinase inhibitor, Ro 28-2653 [J].
Daniewski, AR ;
Liu, W ;
Okabe, M .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (03) :411-414
[5]   Crystal structure and conformation of Linomide [N-methyl-N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide]:: A novel immunomodulator [J].
Dasari, KB ;
Srikrishnan, T .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2002, 32 (12) :499-504
[6]   Angiogenesis inhibitors in lung cancer: A promise fulfilled [J].
Dy, Grace K. ;
Adjei, Alex A. .
CLINICAL LUNG CANCER, 2006, 7 :S145-S149
[7]   Modulation of mitogen-activated protein kinases by 6-nitro-7-hydroxycoumarin mediates apoptosis in renal carcinoma cells [J].
Finn, G ;
Creaven, B ;
Egan, D .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2003, 481 (2-3) :159-167
[8]   Identification of coumarin derivatives as a novel class of allosteric MEK1 inhibitors [J].
Han, SL ;
Zhou, V ;
Pan, SF ;
Liu, Y ;
Hornsby, M ;
McMullan, D ;
Klock, HE ;
Haugen, J ;
Lesley, SA ;
Gray, T ;
Caldwell, J ;
Gu, XJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (24) :5467-5473
[9]  
Joseph IBJK, 1996, CANCER RES, V56, P3404
[10]   3-Bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo [J].
Kempen, I ;
Papapostolou, D ;
Thierry, N ;
Pochet, L ;
Counerotte, S ;
Masereel, B ;
Foidart, JM ;
Reboud-Ravaux, M ;
Noël, A ;
Pirotte, B .
BRITISH JOURNAL OF CANCER, 2003, 88 (07) :1111-1118