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Synthesis and screening of substituted 1,4‐naphthoquinones (NPQs) as antifilarial agents
Author(s) -
Mathew Nisha,
Karunan Twinkle,
Srinivasan Lakshmy,
Muthuswamy Kalyanasundaram
Publication year - 2010
Publication title -
drug development research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.582
H-Index - 60
eISSN - 1098-2299
pISSN - 0272-4391
DOI - 10.1002/ddr.20357
Subject(s) - dichloromethane , chemistry , bromide , naphthalene , ethanol , chromatography , naphthoquinone , solvent , proton nmr , high performance liquid chromatography , column chromatography , dipeptide , organic chemistry , stereochemistry , amino acid , biochemistry
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, 13 C‐NMR, 1 H‐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 MTT (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 (ED 50 values of 0.91 and 1.2 µM, respectively, at 48 h). The effect of different substitutions on antifilarial activity is discussed. Drug Dev Res 2009. © 2009 Wiley‐Liss, Inc.