Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase

Behçet, Ayten; Çağlılar, Tuba; Celepci, Duygu Barut; Aktaş, Aydın; Taslimi, Parham; Gök, Yetkın; Aygün, Muhıttın; Kaya, Rüya; Gülçın, İlhami

doi:10.1016/j.molstruc.2018.05.077

Cited by 74 publications

(53 citation statements)

References 72 publications

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“…α‐Glycosidase inhibitory efficacy of pyrazoles derivatives ( 1–8 ) was performed using p ‐nitrophenyl‐ d ‐glycopyranoside ( p ‐NPG) as the substrate, according to the former procedure . Samples were prepared by dissolving 10 mg in 10 mL (EtOH/H 2 O).…”

Section: Methodsmentioning

confidence: 99%

Some pyrazoles derivatives: Potent carbonic anhydrase, α‐glycosidase, and cholinesterase enzymes inhibitors

Türkan

Çetin

Taslimi

et al. 2018

Archiv der Pharmazie

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A series of substituteed pyrazol‐4‐yl‐diazene derivatives were found to be effective inhibitors against α‐glycosidase, cytosolic carbonic anhydrase I and II isoforms (hCA I and II), butyrylcholinesterase (BChE), and acetylcholinesterase (AChE) with Ki values in the range of 33.72 ± 7.93 to 90.56 ± 27.52 nM for α‐glycosidase, 1.06 ± 0.16 to 9.83 ± 0.74 nM for hCA I, 0.68 ± 0.12 to 7.16 ± 1.14 nM for hCA II, 44.66 ± 10.06 to 78.34 ± 17.83 nM for AChE, and 50.36 ± 13.88 to 88.36 ± 20.03 nM for BChE, respectively. Recently, inhibition of these metabolic enzymes has been considered as a promising factor for pharmacologic intervention in a diversity of disturbances, such as diabetes, glaucoma, obesity, epilepsy, cancer, and neurodegenerative diseases.

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Section: Methodsmentioning

confidence: 99%

Some pyrazoles derivatives: Potent carbonic anhydrase, α‐glycosidase, and cholinesterase enzymes inhibitors

Türkan

Çetin

Taslimi

et al. 2018

Archiv der Pharmazie

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“…Recent attention has focused on AChE and its possible use in therapy for AD. AChE and BChE have been identified in amyloid plaques and neurofibrillary tangles . AChE has been detected as the dominant enzyme in the normal brain.…”

Section: Discussionmentioning

confidence: 99%

Inhibition profiles of Voriconazole against acetylcholinesterase, α‐glycosidase, and human carbonic anhydrase I and II isoenzymes

Topal

2019

J Biochem & Molecular Tox

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In this work, the inhibitory activity of Voriconazole was measured against some metabolic enzymes, including human carbonic anhydrase (hCA) I and II isoenzymes, acetylcholinesterase (AChE), and α‐glycosidase; the results were compared with standard compounds including acetazolamide, tacrine, and acarbose. Half maximal inhibition concentration (IC50) values were obtained from the enzyme activity (%)‐[Voriconazole] graphs, whereas Ki values were calculated from the Lineweaver‐Burk graphs. According to the results, the IC50 value of Voriconazole was 40.77 nM for α‐glycosidase, while the mean inhibition constant (Ki) value was 17.47 ± 1.51 nM for α‐glycosidase. The results make an important contribution to drug design and have pharmacological applications. In addition, the Voriconazole compound demonstrated excellent inhibitory effects against AChE and hCA isoforms I and II. Voriconazole had Ki values of 29.13 ± 3.57 nM against hCA I, 15.92 ± 1.90 nM against hCA II, and 10.50 ± 2.46 nM against AChE.

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“…Compound 10 (494.42 g/mol) was synthesized from 1‐(2,3,5,6‐tetramethylbenzyl)benzimidazole (0.9 g, 1 mmol) and 1‐(2‐bromoethyl)‐4‐nitrobenzene (0.78 g, 1 mmol) according to the same conditions and procedure as for 2 . The final product was crystallized in ethyl alcohol.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and In Vitro Anticancer Evaluation of Some Benzimidazolium Salts

Akkoç

Kayser

2019

Journal of Heterocyclic Chem

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A series of benzimidazolium salts having 2‐cyanobenzyl (2–6), 2‐(4‐nitrophenyl)ethyl (7–10), (1,3‐dioxoisoindolin‐2‐yl)butyl (11–17) or N‐methylphthalimide (18–22) substitution were synthesized and characterized by spectroscopic and analytical techniques. The in vitro cytotoxic activity of these salts was tested against human colon cancer (DLD‐1), human breast cancer (MDA‐MB‐231), and normal human noncancerous embryonic kidney (HEK‐293T) cell lines using the MTT assay method. The viability rates of the cells were determined by confocal microscopy. The majority of the newly synthesized compounds, with the exception of compounds 2, 3, 8, 11, 12, and 17, displayed high cytotoxic activity against cancerous cells. In fact, compounds 6 and 7 exhibited better results than the positive control drugs, cisplatin and busulfan, against the MDA‐MB‐231 cells. Therefore, compounds 6 and 7 could be considered as anticancer drug candidates for further development.

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Synthesis, characterization and crystal structure of 2-(4-hydroxyphenyl)ethyl and 2-(4-nitrophenyl)ethyl Substituted Benzimidazole Bromide Salts: Their inhibitory properties against carbonic anhydrase and acetylcholinesterase

Cited by 74 publications

References 72 publications

Some pyrazoles derivatives: Potent carbonic anhydrase, α‐glycosidase, and cholinesterase enzymes inhibitors

Some pyrazoles derivatives: Potent carbonic anhydrase, α‐glycosidase, and cholinesterase enzymes inhibitors

Inhibition profiles of Voriconazole against acetylcholinesterase, α‐glycosidase, and human carbonic anhydrase I and II isoenzymes

Synthesis and In Vitro Anticancer Evaluation of Some Benzimidazolium Salts

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