Exploiting a basic chemosensitizing pharmacophore hypothesis. Part 1: Synthesis and biological evaluation of novel arylbromide and bicyclic chemosensitizers against drug-resistant malaria parasites

被引：10
作者：
Chouteau, F
Ramanitrahasimbola, D
Rasoanaivo, P
Chibale, K
机构：
[1] Inst Malgache Rech Appl, Lab Pharmacognosie Appl Maladies Infect, Antananarivo 101, Madagascar
[2] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 12期
基金：
新加坡国家研究基金会;
关键词：
malaria; chloroquine; chemosensitizers;
D O I：
10.1016/j.bmcl.2005.04.033
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
An exploratory series of novel arylbromide and bicyclic chemosensitizers (modulators) against chloroquine-resistant Plasinodium falciparum were designed and synthesized on the basis of a basic chemosensitizing pharmacophore hypothesis in malaria. ortho-Substituted bromo and biphenyl ether compounds displayed the best activity from the series. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3024 / 3028
页数：5
相关论文
共 17 条
[1]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[2]   Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents [J].
Chibale, K ;
Visser, M ;
van Schalkwyk, D ;
Smith, PJ ;
Saravanamuthu, A ;
Fairlamb, AH .
TETRAHEDRON, 2003, 59 (13) :2289-2296
[3]   Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].
Evans, DA ;
Katz, JL ;
West, TR .
TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940
[4]   Between hope and a hard place [J].
Greenwood, B .
NATURE, 2004, 430 (7002) :926-927
[5]   Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum [J].
Guan, J ;
Kyle, DE ;
Gerena, L ;
Zhang, QA ;
Milhous, WK ;
Lin, AJ .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (13) :2741-2748
[6]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[7]   Structural properties of dibenzosuberanylpiperazine derivatives for efficient reversal of chloroquine resistance in Plasmodium chabaudi [J].
Osa, Y ;
Kobayashi, S ;
Sato, Y ;
Suzuki, Y ;
Takino, K ;
Takeuchi, T ;
Miyata, Y ;
Sakaguchi, M ;
Takayanagi, H .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (10) :1948-1956
[8]   Reversal activity of the naturally occurring chemosensitizer malagashanine in Plasmodium malaria [J].
Rafatro, H ;
Ramanitrahasimbola, D ;
Rasoanaivo, P ;
Ratsimamanga-Urverg, S ;
Rakoto-Ratsimamanga, A ;
Frappier, F .
BIOCHEMICAL PHARMACOLOGY, 2000, 59 (09) :1053-1061
[9]  
Rasoanaivo P, 1996, CURR MED CHEM, V3, P1
[10]   Alkaloids of Hernandia voyronii: Chloroquine-potentiating activity and structure elucidation of herveline D [J].
Rasoanaivo, P ;
Ratsimamanga-Urverg, S ;
Rafatro, H ;
Ramanitrahasimbola, D ;
Palazzino, G ;
Galeffi, C ;
Nicoletti, M .
PLANTA MEDICA, 1998, 64 (01) :58-62
12