Quantitative structure-activity relationships to predict antibacterial effect of some benzimidazole derivatives

Podunavac-Kuzmanovic, O Sanja; Barna, J Dijana; Cvetković, Dragoš

doi:10.2298/apt0839181p

Cited by 6 publications

(10 citation statements)

References 13 publications

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“…The structures of benzimidazole derivatives (n = 42) included in the study were selected from the literature. Compounds bearing 2-aminobenzimidazole (1-3) and hydrazone moieties (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) were presented in the study by Özkay et al 2011 (14). They reported that synthesized novel benzimidazole-hydrazone exhibited low antibacterial activity, while in contrast the compound showed significant antifungal activity against Candida yeasts.…”

Section: Data Sources For In Silico Assessmentmentioning

confidence: 99%

“…The group of thiazolobenzimidazolones did not express their antibacterial activity against tested strains. 2-Methylbenzimidazole (29), 1-substituted-2-methylbenzimidazoles (30-35), 2-aminobenzimidazole (36) and 1-substituted-2-aminobenzimidazoles (37-42) were previously reported to express effective antifungal activity against Saccharomyces cerevisiae (6).…”

Section: Data Sources For In Silico Assessmentmentioning

confidence: 99%

“…It is considered that antibacterial ability of these compounds is, among everything else, precisely the result of competition with purine bases which results in the inhibition of nucleic acid and cell wall protein synthesis (4,5). Fungicidal mechanisms of this component are facilitated by inhibition the synthesis of estrogen, which is a component of the cell membrane of fungi (6,7). Apart from antimicrobial properties, various substituted derivatives of benzimidazole nucleus induce anthelmintic (2), antihypertensive (8), anti-inflammatory (9), antiviral (10), antioxidative (11), anticancerogenic (12), anticoagulative effects (13), as well as many other downstream activities.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

In Silicoevaluation of Selected Benzimidazole Derivatives in the Discovery of New Potent Antimicrobial Agents

Živković¹,

Kalauzović²,

Milosavljević³

et al. 2019

AMM

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Benzimidazoles are heterocyclic compounds that represent pharmacophores of many drugs. Apart from antimicrobial (antibacterial and antifungal) activities, benzimidazole derivatives are remarkably effective compounds possessing a wide spectrum of biological activities. Pharmacokinetic and toxicological properties of forty-two benzimidazole derivatives were calculated using Molinspiration, SwissADME and OSIRIS Data Warrior. The properties of benzimidazoles were compared to those of doxycycline, chloramphenicol and ketoconazole. The compounds met all criteria for satisfying oral bioavailability. The majority of tested benzimidazoles is considered non-toxic, and the irritating behaviour was not observed in any of the cases. Finally, the most promising nine derivatives were selected on the basis of favourable pharmacokinetic parameters and toxicological characteristics. The ability to pass through the hematoencephalic barrier is expected for all components except one, and none of the selected components is a substrate for P-glycoprotein. In addition, metabolic properties are favourable since all the selected components are expected to inhibit not more than three Cytochrome P450 isoenzymes and to be non-toxic.

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Section: Data Sources For In Silico Assessmentmentioning

confidence: 99%

Section: Data Sources For In Silico Assessmentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

In Silicoevaluation of Selected Benzimidazole Derivatives in the Discovery of New Potent Antimicrobial Agents

Živković¹,

Kalauzović²,

Milosavljević³

et al. 2019

AMM

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“…One method that has been extensively employed involves the QSAR approach together with multivariate data analysis, combined with statistical design (Vasanthanathan et al, 2006). This approach is an attempt to show that there is a relationship between biological activities of compounds and structural or molecular descriptors such as physicochemical, thermodynamic, electronic, topological or geometrical parameters (Podunavac-Kuzmanović et al, 2008). The importance of the lipophilic or hydrophobic nature of bioactive compounds has been brought into fore by the tremendous progress in the use of QSAR methods.…”

Section: Antimicrobial Evaluationmentioning

confidence: 99%

1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity

Fadare¹,

Akinpelu²,

Ejemubu³

et al. 2014

Afr. J. Pure Appl. Chem.

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Chalcones are natural biocides. Several publications appear every year covering the synthesis of chalcones because they exhibit an array of pharmacological activities. In this study, some condensation reactions of 1-Indanone with substituted benzaldehydes were carried out under different reaction conditions. The chalcone products were converted to their corresponding 2,4-Dinitrophenylhydrazone derivatives and evaluated against five gram-positive and eight gram-negative bacteria for their in vitro antibacterial property. Antimicrobial activity was observed against many of the tested strains, with zones of inhibition ranging from 10 to 28 mm. In many cases, the hydrazone derivatives were more active than their chalcone precursors. The best results were obtained against gram-negative bacteria for most of the compounds. Compound 1b was the most active with its minimum inhibitory concentrations (MICs) against six strains of bacteria ranging from 15.6 to 31.3 µg/ml, hence, could be developed as an antibacterial agent against infections caused by some gramnegative bacteria such as Pseudomonas aeruginosa and Salmonella typhimurium.

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“…Several thousands of benzimidazole analogs have been synthesized and screened for their antimicrobial activity up-to-date (Podunavac-Kuzmanovic et al, 2008). The cause of a special notice on benzimidazole compounds has been cyanocobalamine (vitamin B 12 ) which bears 5,6-dimethylbenzimidazole fragment and is capable of inducing the growth of bacteria.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of a new series of benzimidazole derivatives

et al. 2011

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Due to antimicrobial importance of benzimidazoles and hydrazones, some benzimidazole-hydrazone compounds were synthesized to screen their antimicrobial activity. Structures of the synthesized compounds were elucidated by (1)H-NMR, IR and ES-MS spectral data and elemental analysis. The synthesized benzimidazole-hydrazones exhibited very weak antibacterial activity. However, antifungal activity of some of the synthesized compounds was very notable against Candida species. The compounds displaying important antifungal activity were screened for their toxicity. Artemia salina 96-well assay was used to determine cytotoxicity of the compounds. Tested compounds exhibited toxicity to different extents (LD(50) = 126.33-368.72 μg/mL). Nevertheless, determination of 3-14 folds higher LD(50) than minimum inhibitory concentration is a significant finding, which demonstrates that the compounds display antifungal activity at non-toxic concentration.

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Quantitative structure-activity relationships to predict antibacterial effect of some benzimidazole derivatives

Cited by 6 publications

References 13 publications

In Silicoevaluation of Selected Benzimidazole Derivatives in the Discovery of New Potent Antimicrobial Agents

In Silicoevaluation of Selected Benzimidazole Derivatives in the Discovery of New Potent Antimicrobial Agents

1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity

Antimicrobial activity of a new series of benzimidazole derivatives

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