Synthesis and biological evaluation of novel benzoquinones as potential antimicrobial agents

Chaaban, I.; Khawass, El Sayeda M. El; Mahran, Mona A.; Razik, Heba A. Abd El; Salamouni, Nehad S. El; Wahab, Abdel

doi:10.1007/s00044-012-0076-0

Cited by 3 publications

(1 citation statement)

References 30 publications

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“…Some alternatives to the azoles are extracts from plants (like the oils from Iamium album, Cuminum cyminum, Salvadora persica) [8,9], the combination of terpenes and fluconazole [10], bioremediation [11], as well as other agents [12,13].…”

Section: Introductionmentioning

confidence: 99%

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

et al. 2014

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Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multicomponent reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different structural features, were tested as anti-yeast agents inhibiting Candida albicans. The effect towards the test strain was studied with a microdilution approach and three different concentrations (150, 300 and 450 µg/mL) were tested. The best results were found for the aminobenzylnaphthols obtained from 1-naphthylethylamine and from natural prolinol. The use of the two-way ANOVA highlighted the better performances of the prolinol derivative among the differently structured aminobenzylnaphthols that were screened. The activity towards C. albicans of this prolinol derivative resulted to be interesting and could represent a promising alternative to overcome the problem of the strains resistant to the traditional antifungals.

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Section: Introductionmentioning

confidence: 99%

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

et al. 2014

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Synthesis and evaluation of new phenolic derivatives as antimicrobial and antioxidant agents

et al. 2017

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Antifungal Activity and In Silico Studies on 2-Acylated Benzo- and Naphthohydroquinones

2022

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The high rates of morbidity and mortality due to fungal infections are associated with a limited antifungal arsenal and the high toxicity of drugs. Therefore, the identification of novel drug targets is challenging due to the several resemblances between fungal and human cells. Here, we report the in vitro antifungal evaluation of two acylphenols series, namely 2-acyl-1,4-benzo- and 2-acyl-1,4-naphthohydroquinones. The antifungal properties were assessed on diverse Candida and filamentous fungi strains through the halo of inhibition (HOI) and minimal inhibitory concentration (MIC). The antifungal activities of 2-acyl-1,4-benzohydroquinone derivatives were higher than those of the 2-acyl-1,4-naphthohydroquinone analogues. The evaluation indicates that 2-octanoylbenzohydroquinone 4 is the most active member of the 2-acylbenzohydroquinone series, with MIC values ranging from 2 to 16 μg/mL. In some fungal strains (i.e., Candida krusei and Rhizopus oryzae), such MIC values of compound 4 (2 and 4 μg/mL) were comparable to that obtained by amphotericin B (1 μg/mL). The compound 4 was evaluated for its antioxidant activity by means of FRAP, ABTS and DPPH assays, showing moderate activity as compared to standard antioxidants. Molecular docking studies of compound 4 and ADMET predictions make this compound a potential candidate for topical pharmacological use. The results obtained using the most active acylbenzohydroquinones are promising because some evaluated Candida strains are known to have decreased sensitivity to standard antifungal treatments.

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Synthesis and biological evaluation of novel benzoquinones as potential antimicrobial agents

Cited by 3 publications

References 30 publications

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

Synthesis and evaluation of new phenolic derivatives as antimicrobial and antioxidant agents

Antifungal Activity and In Silico Studies on 2-Acylated Benzo- and Naphthohydroquinones

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