Synthesis and Screening of Substituted 1,4-Naphthoquinones (NPQs) as Antifilarial Agents

被引：18
作者：
Mathew, Nisha [1 ]
Karunan, Twinkle [1 ]
Srinivasan, Lakshmy [1 ]
Muthuswamy, Kalyanasundaram [1 ]
机构：
[1] Indian Council Med Res, Vector Control Res Ctr, Pondicherry 605006, India
来源：
DRUG DEVELOPMENT RESEARCH | 2010年 / 71卷 / 03期
关键词：
1; 4-naphthoquinone; antifilarial; macrofilaricide; filariasis; Setaria digitata; STREBLUS-ASPER; DERIVATIVES; INHIBITORS; SULFONATE; QUINONES; ENZYMES;
D O I：
10.1002/ddr.20357
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Eleven amino-substituted 1,4-naphthoquinones were synthesized via the reaction of 1,4-naphthoquinone with different primary and secondary mono- and diamines in the presence of dichloromethane ethanol (1:2) solvent at room temperature. All compounds were purified by flash column chromatography, characterized by TLC, HPLC, C-13-NMR, H-1-NMR, and FT-IR spectral analysis and were evaluated in vitro for antifilarial activity using adult bovine filarial worm Setaria digitata by assessing worm motility and MIT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) reduction. Seven of the 11 compounds had macrofilaricidal activity with compounds 9 (2-[(1,3-dimethylbutyl) amino] naphthalene-1,4-dione) and 11 (2-(4-methylpiperazin-1-yl) naphthalene-1,4-dione) having maximum activity (ED50 values of 0.91 and 1.2 mu M, respectively, at 48 h). The effect of different substitutions on antifilarial activity is discussed. Drug Dev Res 71:188-196, 2010. (C) 2009 Wiley-Liss, Inc,
引用
收藏
页码：188 / 196
页数：9
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