Exploring electronic structure, and substituent effect of some biologically active benzimidazole derivatives: Experimental insights and DFT calculations

Shehab, Ola R.; Mansour, Ahmed M.

doi:10.1016/j.molstruc.2020.128996

Cited by 7 publications

(3 citation statements)

References 43 publications

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“…Metronidazole, thiabendazole, misonidazole, omeprazole, astemizole, clotrimazole, azomycin, cimetidine, and antihistamines are examples of comparable products used in the veterinary, pharmaceutical, and agricultural industries (Al-Muhaimeed, 1997). Drugs containing the benzimidazole moiety have a wide range of pharmacological properties, including bactericidal (Carcanague et al, 2002;Shehab and Mansour, 2021), analgesic (Demirayak et al, 2005;Aghatabay et al, 2007), fungicidal (Solel, 1970;Lezcano et al, 2002), antiviral (Tewari and Mishra, 2006;Tonelli et al, 2008), anti-malarial (Worachartcheewan et al, 2013, HIV-1 infectivity inhibition (Gardiner et al, 1995;Kanwal et al, 2019), AChE and BuChE inhibition (Dinparast et al, 2021;Türkan, 2021), antioxidant (Ayhan-Kilcigil et al, 2004;Usta et al, 2015), and antileishmanial (Mayence et al, 2008) effects. In the field of current medicinal chemistry, researchers have shown that the hybridization of two or more molecules with various bioactive structural motifs is an efficient method for creating novel chemical entities with improved pharmacological properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro biological assessment, and molecular docking study of benzimidazole-based thiadiazole derivatives as dual inhibitors of α-amylase and α-glucosidase

et al. 2023

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The clinical significance of benzimidazole-containing drugs has increased in the current study, making them more effective scaffolds. These moieties have attracted strong research interest due to their diverse biological features. To examine their various biological significances, several research synthetic methodologies have recently been established for the synthesis of benzimidazole analogs. The present study aimed to efficiently and quickly synthesize a new series of benzimidazole analogs. Numerous spectroscopic techniques, including 1H-NMR, 13C-NMR, and HREI-MS, were used to confirm the synthesized compounds. To explore the inhibitory activity of the analogs against α-amylase and α-glucosidase, all derivatives (1–17) were assessed for their biological potential. Compared to the reference drug acarbose (IC50 = 8.24 ± 0.08 µM), almost all the derivatives showed promising activity. Among the tested series, analog 2 (IC50 = 1.10 ± 0.10 & 2.10 ± 0.10 µM, respectively) displayed better inhibitory activity. Following a thorough examination of the various substitution effects on the inhibitory capacity of α-amylase and α-glucosidase, the structure-activity relationship (SAR) was determined. We looked at the potential mechanism of how active substances interact with the catalytic cavity of the targeted enzymes in response to the experimental results of the anti-glucosidase and anti-amylase. Molecular docking provided us with information on the interactions that the active substances had with the various amino acid residues of the targeted enzymes for this purpose.

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Section: Introductionmentioning

confidence: 99%

Synthesis, in vitro biological assessment, and molecular docking study of benzimidazole-based thiadiazole derivatives as dual inhibitors of α-amylase and α-glucosidase

et al. 2023

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“…However, it should be noted that introducing a substituent at the para-position of the aniline moiety of benzimidazole derivatives leads to a reduction in antibacterial activity. 19 In the research conducted on pyrazoles-sulfonamide hybrid (PSH) compounds, it was observed that pyrazole derivatives containing a sulfonamide group exhibited signi cant antimicrobial activity compared to pyrazole when evaluated as antimicrobial agents. 20 Molecular docking analysis was conducted against the dihydropteroate synthase (DHPS) receptors of Staphylococcus aureus and Escherichia coli bacterial strains.…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking Investigation and Pharmacokinetic Properties Prediction of Some Benzimidazole Analogues as Dihydropteroate Synthase (DHPS) Inhibitors

Salubi

2023

Preprint

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Recent research has established the classification of benzimidazole as a privileged structure owing to its strong binding affinity to protein receptors and diverse enzymes. Extensive investigations have consistently shown the antimicrobial potential of benzimidazole derivatives against a wide range of microbial strains. In order to gain a deeper understanding of the relationship between structural modifications and the antibacterial effectiveness of sulfonamide compounds, we have developed targeted derivatives with subtle alterations in the aromatic ring of sulfonamides and the substituent groups. Furthermore, we present the results of molecular docking analyses, ADMET properties, and drug-likeness assessment to evaluate the potential of these compounds to interact with dihydropteroate synthase, a key enzyme involved in bacterial growth. The compounds exhibited a favourable binding affinity, ranging from 7.1 to 7.9 kcal/mol, which surpasses that of the standard drugs sulfamethazine and sulfamethoxazole, with binding affinities of 5.9 and 6.1 kcal/mol, respectively. Furthermore, these compounds demonstrated good oral bioavailability and exhibited favourable drug-like properties.

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“…Yang et al experimentally speculated that Fe(VI) is involved in both single-electron transfer (SET) and double electron transfer during the oxidation of ciprofloxacin and enrofloxacin . At the same time, numerous studies have shown that the kind and position of the substituents affect the physicochemical properties of the compound and then affect the reaction mechanism. − At present, there have been no studies on the effect of the type and position of ring substituents on the reaction mechanism of SANs and Fe(VI). ,,− …”

Section: Introductionmentioning

confidence: 99%

Ferrate(VI) Oxidation Mechanism of Substituted Anilines: A Density Functional Theory Investigation

Tian

Wang

et al. 2021

ACS Omega

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Ferrate(VI) (Fe(VI)) is a promising oxidant coagulant and disinfectant for the degradation of organic micropollutants. However, it is hard to elucidate the detailed oxidation mechanism through the current experimental approaches. Substituted anilines (SANs) are important chemical compounds that are widely used in many industries. This paper presents the use of density functional theory (DFT) to understand the oxidation mechanism of SANs by Fe(VI) and the effect of substituents. The calculation results revealed that the primary oxidations of SANs follow the hydrogen atom transfer (HAT) mechanism. Interestingly, the hydroxyl oxygen of HFeO 4− is more reactive than the carbonyl oxygen when reacting with SANs. The formation of the SAN radical is crucial, and all of the products are formed from it. Azobenzene is more favorable to generate the above products. In addition, the obtained results indicate that this kind of substituent has a much greater influence on the reaction rather than the position. Thus, the present study provides a valuable insight into the transformation pathways of SANs in the Fe(VI) oxidation process and the effects of the substituent on oxidation. These results will advance the understanding of Fe(VI) involved in wastewater treatment.

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Exploring electronic structure, and substituent effect of some biologically active benzimidazole derivatives: Experimental insights and DFT calculations

Cited by 7 publications

References 43 publications

Synthesis, in vitro biological assessment, and molecular docking study of benzimidazole-based thiadiazole derivatives as dual inhibitors of α-amylase and α-glucosidase

Synthesis, in vitro biological assessment, and molecular docking study of benzimidazole-based thiadiazole derivatives as dual inhibitors of α-amylase and α-glucosidase

Molecular Docking Investigation and Pharmacokinetic Properties Prediction of Some Benzimidazole Analogues as Dihydropteroate Synthase (DHPS) Inhibitors

Ferrate(VI) Oxidation Mechanism of Substituted Anilines: A Density Functional Theory Investigation

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