Antimalarial activity of ferrocenyl chalcones

被引:170
作者
Wu, X
Wilairat, P
Go, ML
机构
[1] Natl Univ Singapore, Dept Pharm, Singapore 117543, Singapore
[2] Mahidol Univ, Dept Biochem, Bangkok 10400, Thailand
关键词
D O I
10.1016/S0960-894X(02)00430-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of ferrocenyl chalcones were synthesized and evaluated for in vitro antimalarial activity against a chloroquine-resistant strain of Plasmodium falciparum. The most active compounds were 1-(3-pyridyl)-3-ferrocenyl-2-propen-1-one (6) and 1-ferrocenyl-3-(4-nitrophenyl)-2-propen-1-one (28) with IC50 of 4.5 and 5.1 muM, respectively. Differences in activity were not readily explained by the size and lipophilicity characteristics of these compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2299 / 2302
页数:4
相关论文
共 11 条
[1]   Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue [J].
Biot, C ;
Glorian, G ;
Maciejewski, LA ;
Brocard, JS ;
Domarle, O ;
Blampain, G ;
Millet, P ;
Georges, AJ ;
Abessolo, H ;
Dive, D ;
Lebibi, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (23) :3715-3718
[2]   Synthesis and antimalarial activity in vitro of potential metabolites of ferrochloroquine and related compounds [J].
Biot, C ;
Delhaes, L ;
N'Diaye, CM ;
Maciejewski, LA ;
Camus, D ;
Dive, D ;
Brocard, JS .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (12) :2843-2847
[3]   In vitro and in vivo antimalarial activity of ferrochloroquine, a ferrocenyl analogue of chloroquine against chloroquine-resistant malaria parasites [J].
Delhaes, L ;
Abessolo, H ;
Biot, C ;
Berry, L ;
Delcourt, P ;
Maciejewski, L ;
Brocard, J ;
Camus, D ;
Dive, D .
PARASITOLOGY RESEARCH, 2001, 87 (03) :239-244
[4]   Novel ferrocenic artemisinin derivatives: Synthesis, in vitro antimalarial activity and affinity of binding with ferroprotoporphyrin IX [J].
Delhaes, L ;
Biot, C ;
Berry, L ;
Maciejewski, LA ;
Camus, D ;
Brocard, JS ;
Dive, D .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (12) :2739-2745
[5]   In vitro antimalarial activity of a new organometallic analog, ferrocene-chloroquine [J].
Domarle, O ;
Blampain, G ;
Agnaniet, H ;
Nzadiyabi, T ;
Lebibi, J ;
Brocard, J ;
Maciejewski, L ;
Biot, C ;
Georges, AJ ;
Millet, P .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (03) :540-544
[6]  
Hansch C., 1979, Substituent constants for correlation analysis in chemistry and biology
[7]   Novel N-ferrocenylmethyl, N′-methyl-2-substituted benzimidazolium iodide salts with in vitro activity against the P-falciparum malarial parasite strain NF54 [J].
Howarth, J ;
Hanlon, K .
TETRAHEDRON LETTERS, 2001, 42 (04) :751-754
[8]   Synthesis of novel ferrocenyl sugars and their antimalarial activities [J].
Itoh, T ;
Shirakami, S ;
Ishida, N ;
Yamashita, Y ;
Yoshida, T ;
Kim, HS ;
Wataya, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (15) :1657-1659
[9]  
KUBINYI H, 1995, BURGERS MED CHEM DRU, V1, P497
[10]   Antimalarial alkoxylated and hydroxylated chalones: Structure-activity relationship analysis [J].
Liu, M ;
Wilairat, P ;
Go, ML .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (25) :4443-4452