Synthesis and in vitro activities of ferrocenic aminohydroxynaphthoquinones against Toxoplasma gondii and Plasmodium falciparum

Baramee, Apiwat; Coppin, Alexandra; Mortuaire, Marlène; Pélinski, Lydie; Tomavo, Stanislas; Brocard, Jacques

doi:10.1016/j.bmc.2005.09.054

Cited by 116 publications

(83 citation statements)

References 23 publications

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“…Other compounds such as amino-terpenyl naphthoquinones, b-carboline alkaloids, analogues dextran sulfate, bisphosphonates, ferrocenyl aminohydroxynaphthoquinones, and ivermectin displayed anti-parasitic properties toward T. gondii, however the mechanism of this activity has not been explained [60][61][62][63][64][65].…”

Section: Other Synthetic Compoundsmentioning

confidence: 93%

Human toxoplasmosis–Searching for novel chemotherapeutics

Antczak

Dzitko

Długońska

2016

Biomedicine & Pharmacotherapy

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Section: Other Synthetic Compoundsmentioning

confidence: 93%

Human toxoplasmosis–Searching for novel chemotherapeutics

Antczak

Dzitko

Długońska

2016

Biomedicine & Pharmacotherapy

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“…The best results were obtained using a slightly modified procedure, which used 10 mol% of excess amine in order to increase the nucleophilic character of lawsone by deprotonating the hydroxyl and an excess of 20 mol% aldehyde to shift the equilibrium towards the incipient imine or iminium intermediates. 3,14,15 Several solvents were tested and the best results were obtained with ethanol to prepare compound 4 in good yields as a pure red solid after filtration. This protocol allowed to reach the Mannich adducts 5-8 and 10-14 in moderate to high yields using pyrrolidine 3 and p-nitroaniline 9, respectively and various aromatic aldehydes.…”

Section: Synthesis Of Lawsone Derivativesmentioning

confidence: 99%

Synthesis,in vitroAntifungal Activity and Molecular Modeling Studies of New Mannich Bases Derived from Lawsone

Filho¹,

Roldi²,

Delarmelina³

et al. 2016

Journal of the Brazilian Chemical Society

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Hydroxynaphthoquinones such as lawsone (2-hydroxy-1,4-naphthoquinone) have proven to be effective antifungal agents. These compounds were tested for antifungal activity against yeast standard and clinical strains by the broth microdilution method. Among the synthetic lawsone derivatives, 2-hydroxy-3-((2-hydroxyphenyl)(pyrrolidin-1-yl)methyl)naphthalene-1,4-dione, 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione and 2-hydroxy-3-((2-hydroxyphenyl)((4-nitrophenyl)amino)methyl)naphthalene-1,4-dione showed high activity against Candida albicans ATCC 10231, with minimal inhibitory concentrations (MICs) and minimal fungicidal concentrations (MFCs) ranging from 20 to 330 and from 80 to 330 μg mL -1 , respectively. Moreover, they also showed a mechanism of action on exogenous ergosterol. Therapeutic concentrations (CC 50 ) of 2-hydroxy-3-((2-hydroxyphenyl)(pyrrolidin-1-yl)methyl) naphthalene-1,4-dione, 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione and 2-hydroxy-3-((2-hydroxyphenyl)((4-nitrophenyl)amino)methyl)naphthalene-1,4-dione were 52.81, 52.58 and 85.94 μg mL -1 , respectively, which can be considered moderate or low. In addition, docking studies showed that these compounds had similar binding energy to standard ketoconazole, which are recognized as the molecular target by van der Waals interactions. Furthermore, they are under Lipinski's rule of 5 with a druglikeness score better than ketoconazole and nystatin. These findings suggest that 2-hydroxy-3-((2-hydroxyphenyl)(pyrrolidin-1-yl)methyl) naphthalene-1,4-dione, 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione and 2-hydroxy-3-((2-hydroxyphenyl)((4-nitrophenyl)amino)methyl)naphthalene-1,4-dione have potential as leading compounds against human fungal infections.

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“…Therefore, atovaquone derivatives have been synthesized to improve activities and/or pharmacokinetics properties [8,9].…”

Section: Introductionmentioning

confidence: 99%

Microbial Metabolism of Atovaquone and Cytotoxicity of the Produced Phase I Metabolite

Silva

Gonçalves

Santos

et al. 2015

Eur J Drug Metab Pharmacokinet

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Synthesis and in vitro activities of ferrocenic aminohydroxynaphthoquinones against Toxoplasma gondii and Plasmodium falciparum

Cited by 116 publications

References 23 publications

Human toxoplasmosis–Searching for novel chemotherapeutics

Human toxoplasmosis–Searching for novel chemotherapeutics

Synthesis,in vitroAntifungal Activity and Molecular Modeling Studies of New Mannich Bases Derived from Lawsone

Microbial Metabolism of Atovaquone and Cytotoxicity of the Produced Phase I Metabolite

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