Design, synthesis and antiplasmodial activity of novel imidazole derivatives based on 7-chloro-4-aminoquinoline

被引：31
|
作者：
Kondaparla, Srinivasarao [1 ]
Manhas, Ashan [2 ]
Dola, Vasantha Rao [1 ]
Srivastava, Kumkum [2 ]
Puri, Sunil K. [2 ]
Katti, S. B. [1 ]
机构：
[1] Cent Drug Res Inst, CSIR, Med & Proc Chem Div, Sect 10, Sitapur Rd, Lucknow 226031, Uttar Pradesh, India
[2] Cent Drug Res Inst, CSIR, Div Parasitol, Sect 10, Sitapur Rd, Lucknow 226031, Uttar Pradesh, India
来源：
BIOORGANIC CHEMISTRY | 2018年 / 80卷
关键词：
4-Aminoquinoline; Antiplasmodial activity; Heme binding; Chloroquine; Plasmodium falciparum; beta-hematin; In vitro; Chloroquine sensitive strain; Chloroquine resistant strain; CHLOROQUINE-RESISTANT STRAIN; POTENT ANTIMALARIAL AGENTS; IN-VITRO; 4-AMINOQUINOLINE DERIVATIVES; HEMATIN FORMATION; SIDE-CHAIN; ANALOGS; ASSAY;
D O I：
10.1016/j.bioorg.2018.06.012
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：
A series of short chain 4-aminoquinoline-imidazole derivatives have been synthesized in one pot two step multicomponent reaction using van leusen standard protocol. The diethylamine function of chloroquine is replaced by substituted imidazole derivatives containing tertiary terminal nitrogen. All the synthesized compounds were screened against the chloroquine sensitive (3D7) and chloroquine resistant (K1) strains of Plasmodium falciparum. Some of the compounds (6, 8, 9 and 17) in the series exhibited comparable activity to CQ against K1 strain of P. falciparum. All the compounds displayed resistance factor between 0.09 and 4.57 as against 51 for CQ. Further, these analogues were found to form a strong complex with hematin and inhibit the beta-hematin formation, therefore these compounds act via heme polymerization target.
引用
收藏
页码：204 / 211
页数：8
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