Synthesis and screening of substituted 1,4‐naphthoquinones (NPQs) as antifilarial agents

Abstract

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 mM, respectively, at 48 h). The effect of different substitutions on antifilarial activity is discussed. Drug Dev Res 71: 188-196, 2010.

Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles

“…It is believed that the formation of 6_Bu might be originated from the hydrolysis of 5’ in a basic media. A related work for the formation of 5’ ‐like compound was reported . Here, the di‐carbon fragment, C(11)‐C(12), in imidazole ring of 6_Bu shall come from the innate amido‐group in 3 a .…”

Synthesis of N-substituted phthalimidoalkyl 1H-1,2,3-triazoles: a molecular diversity combining click chemistry and ultrasound irradiation

“…2-Amino-1,4-naphthoquinone derivatives are a versatile class of molecules. 19 In this work, we described for the first time the heterocyclic N-substituted phthalimidoalkyl-1,2,3-triazole appending 2-aminomethyl-1,4-naphthoquinone; we named this new class of compounds as ANTP (aminonaphthoquinone-triazole-phthalimide) and they will be the object of studies in the future.…”

Ruthenium(II)‐Catalyzed C–H Alkenylation of Quinones: Diversity‐Oriented Strategy for Trypanocidal Compounds

“…1,4‐Naphthoquinone ( 1a ) was purified via reduced pressure sublimation using a cold finger sublimation apparatus (50 °C, 0.9 mbar) and stored in a glovebox to prevent contact with moisture. Starting materials 1 were prepared following previously methods described in the literature , . Other chemicals were obtained from commercial sources and used without further purification.…”