Evaluation of Activity of Some 2,5-Disubstituted Benzoxazole Derivatives against Acetylcholinesterase, Butyrylcholinesterase and Tyrosinase: ADME Prediction, DFT and Comparative Molecular Docking Studies

Çeli̇k, İsmail; Erol, Meryem; Arpacı, Özlem Temiz; Şenol, Fatma Sezer; Orhan, İlkay Erdoğan

doi:10.1080/10406638.2020.1737827

Cited by 30 publications

(16 citation statements)

References 29 publications

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“…The investigations reveal that benzoxazole and its analogs are compounds that give meaningful results in terms of microbiological (Taşcı et al, 2018) and cytotoxic activity (Zilifdar et al, 2018). Benzoxazole ring system also has a broad spectrum of pharmacological effects such as anti-inflammatory (Sondhi et al, 2006), antiepileptic (Wei et al, 2009), antialzheimer (Celik et al, 2020;Temiz-Arpaci et al, 2016), anti-HIV (Sakamoto et al, 2007), topoisomerase inhibitors (Oksuzoglu et al, 2008), kinase inhibitors (Han et al, 2012), protease inhibitors (Jonckers et al, 2012). Calcimycin and boxazomycin A-B (antimicrobial), flunoxaprofen (non-steroidal anti-inflammatory), pardoprunox (antiparkinsonian), are examples of some drugs carrying benzoxazole ring system (Figure 1).…”

Section: Figure 1 Benzoxazole Derivatives With Various Biological Activitiesmentioning

confidence: 99%

Bazı Yeni Benzoksazol Türevlerinin Sentezi ve Antimikrobiyal ve Sitotoksik Aktivite Çalışmaları

Erol¹,

Çeli̇k²,

Kuyucuklu³

et al. 2021

European Journal of Science and Technology

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There is an urgent need to develop new antimicrobial drugs due to the rapid development of resistance to increasing microbial infectious diseases and drugs used in their treatment. Also, the compounds synthesized for use in cancer treatment limit their use due to their cytotoxic effect on normal cells and cancerous cells, and their side effects are high. For this reason, researches continue to intensify the drugs developed for cancer treatment to be selectively effective on cancer cells and to reduce their side effects as much as possible. Within this study's scope, 7 compounds of 2-(p-substituted phenyl)-5-(2-substitutedacetamido) were synthesized in 3 steps, and their structures were illuminated by HRMS, 1 H-NMR, and 13 C-NMR spectroscopy methods. Their antimicrobial activities were evaluated on 10 different microorganisms. In addition, cytotoxic activities were investigated on MCF-7 and A549 cell lines by the MTT method. As a result of the study, it was determined that the synthesized compounds were both antibacterial and antifungal at MIC values ranging from 64-256 µg/mL, and compound 9 had significant cytotoxic activity on both A549 and MCF-7. The results obtained will make an important contribution to the studies conducted to develop new or alternative antimicrobial and cytotoxic agents.

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Section: Figure 1 Benzoxazole Derivatives With Various Biological Activitiesmentioning

confidence: 99%

Bazı Yeni Benzoksazol Türevlerinin Sentezi ve Antimikrobiyal ve Sitotoksik Aktivite Çalışmaları

Erol¹,

Çeli̇k²,

Kuyucuklu³

et al. 2021

European Journal of Science and Technology

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“…Some benzoxazoles have been described as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors [ 19 , 20 , 21 , 22 ]. Recently, new glycosyl derivatives of benzoxazole were described as AChE inhibitors [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, new glycosyl derivatives of benzoxazole were described as AChE inhibitors [ 23 ]. The most active compounds had IC 50 values against AChE and BChE at low µM levels [ 20 ]. AChE and BChE are enzymes belonging to the group of serine hydrolases.…”

Section: Introductionmentioning

confidence: 99%

Cholinesterases Inhibition, Anticancer and Antioxidant Activity of Novel Benzoxazole and Naphthoxazole Analogs

et al. 2022

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Benzoxazole and naphthoxazole fused systems are found in many biologically active molecules. Novel benzoxazole and naphthoxazole analogs functionalized by the 2,4-dihydroxyphenyl moiety were designed, obtained and evaluated as a broad spectrum of biological potency compounds. Sulfinylbis[(2,4-dihydroxyphenyl)methanethione] or its analogs and 2-aminophenols or 1-amino-2-naphthol were used as starting reagents. 4-(Naphtho[1,2-d][1,3]oxazol-2-yl)benzene-1,3-diol was identified as the most promising compound of the nanomolar activity against AChE (IC50 = 58 nM) of the mixed-type inhibition and of the moderate activity against BChE (IC50 = 981 nM). The higher antiproliferative potency against a panel of human cancer cell lines for naphtho[1,2-d][1,3]oxazoles than for benzoxazoles was found. The activity of the analog with chlorine atom was in the range of 2.18–2.89 µM (IC50) against all studied cells and it is similar to that of cisplatin studied comparatively. Moreover, this compound was not toxic at this concentration to human normal breast cells and keratinocytes. For some compounds it also has proved antioxidant properties at the level of IC50 = 0.214 µM, for the most active compound. The lipophilicity of all compounds, expressed as log p values, is within the range recommended for potential drugs. The biological activity profile of the considered analogs and their lipophilic level justify the search for agents used in AD or in anticancer therapy in this group of compounds.

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“…Benzoxazole contains a phenyl ring attached to an oxazole ring [2]. The benzoxazole ring is among the most important heterocyclic molecules in medical chemistry [3]. It is a structural isoster of adenine and guanine, which are associated in the structure of nucleic acids.…”

Section: Introductionmentioning

confidence: 99%

Benzoxazole Derivatives: Qsar and Molecular Docking Studies

Kumar

Yadav

Singh

et al. 2022

Preprint

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The increase of bacterial multidrug resistance, as well as a scarcity of new antibacterial agents, necessitate the research and development of novel antibacterials that escape resistance. The current work employed 46 benzoxazole derivatives to undertake both ligand-based molecular docking and receptor-based quantitative structure activity relationships modelling. On a series of benzoxazole derivatives, a quantitative structure-activity relationship study was first carried out, giving a robust model. According to QSAR models developed, topological parameters, Kier's molecular connectivity indices (1χ, 1χv), and topological indices (R) are mostly relevant for the antimicrobial activity of benzoxazole derivatives. The results of molecular docking revealed that molecules 26, 14, 13, 10 and 3 and Ciprofloxacin had docking score − 6.687, -6.463, -6.414, -6.389, -6.388 and − 6.092 respectively. ADME Analysis results indicated that the compounds (4, 5, 6, 8, 10, 16, 19, 20 showing 1 violation of Lipinski rule of five) all remaining derivatives did not violate any of the Lipinski rule of five and these compounds are selected for further research.

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Evaluation of Activity of Some 2,5-Disubstituted Benzoxazole Derivatives against Acetylcholinesterase, Butyrylcholinesterase and Tyrosinase: ADME Prediction, DFT and Comparative Molecular Docking Studies

Cited by 30 publications

References 29 publications

Bazı Yeni Benzoksazol Türevlerinin Sentezi ve Antimikrobiyal ve Sitotoksik Aktivite Çalışmaları

Bazı Yeni Benzoksazol Türevlerinin Sentezi ve Antimikrobiyal ve Sitotoksik Aktivite Çalışmaları

Cholinesterases Inhibition, Anticancer and Antioxidant Activity of Novel Benzoxazole and Naphthoxazole Analogs

Benzoxazole Derivatives: Qsar and Molecular Docking Studies

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