Antiprotozoal quinones. IV. 2-Amino-1,4-naphthoquinone imines as potential antimalarials

Bullock, F. J.; Tweedie, J. F.; Mcritchie, D. D.; Tucker, Margaret A.

doi:10.1021/jm00297a051

Cited by 19 publications

(9 citation statements)

References 2 publications

(2 reference statements)

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“…[Touraire et al, 1996], and Plasmodium sp. have been reported [Bullock et al, 1970]. In pneumonia caused by Pneumocystis carinii, atovaquone [Williams and Clark, 1998] (2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone) is approved as the drug of choice by the FDA.…”

Section: Introductionmentioning

confidence: 99%

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

Mathew

Karunan

Srinivasan

et al. 2009

Drug Development Research

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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.

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Section: Introductionmentioning

confidence: 99%

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

Mathew

Karunan

Srinivasan

et al. 2009

Drug Development Research

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“…Naphthoquinones are widely distributed in plants, fungi and some animals 1 and many are found to exhibit an interesting range of pharmacological properties including antibacterial, [2] and [3] antiviral, 4 trypanocidal, 5 anticancer, 6 antimalarial, [7] and [8] and antifungal 9 activity. Other quinone-related scaffolds such as 2-H-pyran-3(6H)-one derivatives 10 natalensis 12 and that of diospyrin 22, isolated from this plant, was observed against drugresistant strains of M. tuberculosis.…”

Section: Introductionmentioning

confidence: 99%

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

Mahapatra

Mativandlela

Binneman

et al. 2007

Bioorganic & Medicinal Chemistry

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The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plantderived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e.g. other disulfide reductases). openUP (December 2007) Graphical abstractArticle Outline

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“…1,4-Naphthoquinones are widely distributed in plants, fungi and some animals 1 and many are found to exhibit an interesting range of pharmacological properties, including antibacterial, 2,3 antimicrobial, 4 antiviral, 5 trypanocidal, 6 anticancer, 7 antimalarial, 8,9 and antifungal 10 activities, especially when a hydroxyl group is present at the C5 position. 11 Juglone is a quinone produced in the roots, leaves and bark of walnut trees.…”

Section: Introductionmentioning

confidence: 99%

A theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives

Vessally

Fereyduni

Kamaee

et al. 2011

JSCS

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In the present study, first, the intramolecular proton transfer (IPT) process of juglone and its derivatives were theoretically investigated in the gas phase and the effect of electron-withdrawing and electron-releasing substituents in different positions of the phenyl and benzoquinone rings of juglone on the IPT process was studied in which the geometries, energies and thermodynamic functions of the compounds were obtained using density functional theory (DFT) calculations at the B3LYP/6-31+G(2d,p) level. Next, the influence of IPT on changing the aromaticity of the phenyl and benzoquinone rings was investigated. To determine the aromaticity of the rings, nuclear independent chemical shift (NICS) values were calculated for the ground state and transition state structures (GS 1 , TS and GS 2 ) using the continues set of gauge transformations (CSGT) procedure at the B3LYP/6-311+G(2d,p) level.

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Antiprotozoal quinones. IV. 2-Amino-1,4-naphthoquinone imines as potential antimalarials

Cited by 19 publications

References 2 publications

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

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

Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase

A theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives

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