Synthesis and Antifungal Potential of Some Novel Benzimidazole-1,3,4-Oxadiazole Compounds

Karaburun, Ahmet Çağrı; Çavuşoğlu, Betül Kaya; Çevik, Ulviye Acar; Osmaniye, Derya; Sağlık, Begüm Nurpelin; Levent, Serkan; Özkay, Yusuf; Atlı, Özlem; Koparal, Ali Savaş; Kaplancıklı, Zafer Asım

doi:10.3390/molecules24010191

Cited by 48 publications

(25 citation statements)

References 56 publications

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“…The syntheses of the target compounds 3a – p were realized as summarized in Scheme 1 . Known triazoles 1a – d were synthesized according to our already published method [ 33 , 34 ]. The S -alkylation of the triazole ring of compounds 1a – d with an appropriate 2-bromoacetophenone moiety 2a – d using potassium carbonate as base generated the target derivatives 3a – p .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and AChE-Inhibitory Activity of New Benzimidazole Derivatives

et al. 2019

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Alzheimer’s disease (AD), one of the main causes of aged dementia, is a progressive and degenerative neurological disorder characterized by loss of cognition and memory. Although the symptomatic treatment of AD, particularly acetylcholinesterase inhibitors (AChEIs) based on the ‘cholinergic hypothesis’, has been successful in clinic, at present there is no cure for this disease. In this study, we designed compounds carrying benzimidazole and triazole rings on the same chemical skeleton so as to investigate their potential acetylcholinesterase and butyrylcholinesterase activity. Furthermore, molecular modeling study was performed to determine the binding mode of the best inhibitor to the AChE. Among them, compounds 3d and 3h, which featured 3,4-dihydroxy substitution at the phenyl ring and 5(6)-chloro substitution at the benzimidazole ring were found to be potent inhibitors of AChE. The inhibition kinetics of the two most active derivatives 3d and 3h were further studied. The kinetic displayed increasing slope and increasing intercept, which is consistent with a mixed inhibition. The IC50 and Ki values of 3d are 31.9 ± 0.1 nM and 26.2 nM, respectively. Compound 3h exhibited IC50 of 29.5 ± 1.2 nM and Ki of 24.8 nM. The above data compared favorably with data for donepezil (21.8 ± 0.9 nM) the reference compound in our study.

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Section: Resultsmentioning

confidence: 99%

“…The mixture was cooled and poured into iced-water. The obtained solid was filtered, washed with water, dried and recrystallized from ethanol [ 33 , 34 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and AChE-Inhibitory Activity of New Benzimidazole Derivatives

et al. 2019

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“…Additionally, it is absent in humans, that can contribute with the development of selective drugs against pathogens [ 25 ]. 1,3,4-oxadiazole-based drugs have been widely studied by researchers [ 21 , 22 , 23 , 26 , 27 , 28 , 29 ]. These compounds have a high therapeutic power and broad spectrum of action, such as anticancer, antifungal, antibacterial, antitubercular, anti-inflammatory, antineuropathic, antihypertensive, antihistaminic, antiparasitic, antiobesity, antiviral activity, among others [ 29 ].…”

Section: Discussionmentioning

confidence: 99%

Fungicidal Activity of a Safe 1,3,4-Oxadiazole Derivative Against Candida albicans

et al. 2021

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Candida albicans is the most common species isolated from nosocomial bloodstream infections. Due to limited therapeutic arsenal and increase of drug resistance, there is an urgent need for new antifungals. Therefore, the antifungal activity against C. albicans and in vivo toxicity of a 1,3,4-oxadiazole compound (LMM6) was evaluated. This compound was selected by in silico approach based on chemical similarity. LMM6 was highly effective against several clinical C. albicans isolates, with minimum inhibitory concentration values ranging from 8 to 32 µg/mL. This compound also showed synergic effect with amphotericin B and caspofungin. In addition, quantitative assay showed that LMM6 exhibited a fungicidal profile and a promising anti-biofilm activity, pointing to its therapeutic potential. The evaluation of acute toxicity indicated that LMM6 is safe for preclinical trials. No mortality and no alterations in the investigated parameters were observed. In addition, no substantial alteration was found in Hippocratic screening, biochemical or hematological analyzes. LMM6 (5 mg/kg twice a day) was able to reduce both spleen and kidneys fungal burden and further, promoted the suppresses of inflammatory cytokines, resulting in infection control. These preclinical findings support future application of LMM6 as potential antifungal in the treatment of invasive candidiasis.

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“…In vitro antifungal activity of all derivatives (4a-4j) was evaluated against C. albicans (ATCC 90030), C. glabrata (ATCC 90030), C. krusei (ATCC 6258) ve C. parapsilopsis (ATCC 22019) at concentrations between 1 mg/mL-1.95 μg/mL. Activity studies were conducted following EUCAST protocol in accordance with previous studies reported by our research group (Karaburun et al 2018, Karaburun et al 2019).…”

Section: Antifungal Activitymentioning

confidence: 99%

Evaluation of Antifungal Activity of Some Benzothiazole Derivatives

Osmaniye¹,

Sağlık²,

Çevik³

et al. 2019

Kocatepe Veterinary Journal

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The antifungal activity of the previously synthesized compounds was evaluated in order to provide solutions to the candida-induced diseases in animals. In the present study, 10 benzothiazole derivatives (4a-4j) were resynthesized to evaluate their antifungal activity. IR, 1HNMR, 13C-NMR and HRMS (Infrared Spectroscopy, 1 H Nuclear Magnetic Resonance Spectroscopy, 13 C Nuclear Magnetic Resonance Spectroscopy, High Resolution Mass Spectrometry) spectroscopic methods, determined the structure of the synthesized compounds. MIC50(Minimum Inhibitory Concentration) values of the re-synthesized compounds against Candida species were evaluated by in vitro experiments. As a result of activity studies, it was found that compounds 4c and 4d showed significant activity. Compound 4d was found to be the most potent derivative against Candida krusei with a MIC50 value of 1.95 µg / mL.

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Synthesis and Antifungal Potential of Some Novel Benzimidazole-1,3,4-Oxadiazole Compounds

Cited by 48 publications

References 56 publications

Synthesis and AChE-Inhibitory Activity of New Benzimidazole Derivatives

Synthesis and AChE-Inhibitory Activity of New Benzimidazole Derivatives

Fungicidal Activity of a Safe 1,3,4-Oxadiazole Derivative Against Candida albicans

Evaluation of Antifungal Activity of Some Benzothiazole Derivatives

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