scholarly journals The effect of lipophilicity on the antibacterial activity of some 1-benzylbenzimidazole derivatives

2008 ◽  
Vol 73 (10) ◽  
pp. 967-978 ◽  
Author(s):  
S.O. Podunavac-Kuzmanovic ◽  
D.D. Cvetkovic ◽  
D.J. Barna
Keyword(s):  
Antibacterial Activity ◽  
Quantitative Structure Activity Relationship ◽  
Biologically Active ◽  
Benzimidazole Derivatives ◽  
Log P ◽  
P Values ◽  
High Agreement ◽  
Software Products ◽  
Lipophilicity Parameter ◽  
Qsar Models

In the present paper, the antibacterial activity of some 1-benzylbenzimidazole derivatives were evaluated against the Gram-negative bacteria Escherichia coli. The minimum inhibitory concentration was determined for all the compounds. Quantitative structure-activity relationship (QSAR) was employed to study the effect of the lipophilicity parameters (log P) on the inhibitory activity. Log P values for the target compounds were experimentally determined by the "shake-flask" method and calculated by using eight different software products. Multiple linear regression was used to correlate the log P values and antibacterial activity of the studied benzimidazole derivatives. The results are discussed based on statistical data. The most acceptable QSAR models for the prediction of the antibacterial activity of the investigated series of benzimidazoles were developed. High agreement between the experimental and predicted inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on the antibacterial activity of this class of compounds, which simplifies the design of new biologically active molecules.

scholarly journals Application of QSAR models in analysis of antibacterial activity of some benzimidazole derivatives against Sarcina lutea

2013 ◽  
Vol 67 (1) ◽  
pp. 27-33
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Dragoljub Cvetkovic ◽  
Lidija Jevric ◽  
Natasa Uzelac
Keyword(s):  
Antibacterial Activity ◽  
Inhibitory Activity ◽  
Antibacterial Activities ◽  
Quantitative Structure Activity Relationship ◽  
Benzimidazole Derivatives ◽  
Log P ◽  
Statistical Parameters ◽  
Qsar Analysis ◽  
Qsar Models

In the present paper, a quantitative structure activity relationship (QSAR) has been carried out on a series of 2-methyl and 2-aminobenzimidazole derivatives to identify the lipophilicity requirements for their inhibitory activity against bacteria Sarcina lutea. The tested compounds displayed in vitro antibacterial activity and minimum inhibitory concentration (MIC) was determined for all compounds. The partition coefficients of the studied compounds were measured by the shake flask method (log P) and by theoretical calculation (Clog P). The relationships between lipophilicity descriptors and antibacterial activities were investigated and the mathematical models have been developed as a calibration models for predicting the inhibitory activity of this class of compounds. The models were validated by leave-one-out (LOO) technique as well as by the calculation of statistical parameters for the established models. Therefore, QSAR analysis reveals that lipophilicity descriptor govern the inhibitory activity of benzimidazoles studied against Sarcina lutea.

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

2008 ◽  
pp. 181-191 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Dijana Barna ◽  
Dragoljub Cvetkovic
Keyword(s):  
Antibacterial Activity ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Biologically Active ◽  
Benzimidazole Derivatives ◽  
Quantitative Structure ◽  
Structure Activity ◽  
Lipophilicity Parameter ◽  
Office Software

The antibacterial activity of some substituted benzimidazole derivatives against Gram negative bacteria Escherichia coli was investigated. The tested compounds displayed in vitro inhibitory activity and their minimum inhibitory concentrations were determined. Quantitative structure-activity relationship has been used to study the relationships between the antibacterial activity and lipophilicity parameter, logP. Lipophilicity parameters were calculated for each molecule by using CS Chem-Office Software version 7.0. Multiple linear regression was used to correlate the logP values and antibacterial activity of benzimidazole derivatives. The results are discussed on the basis of statistical data. The most acceptable QSAR model for prediction of antibacterial activity of the investigated series of benzimidazoles was developed. High agreement between experimental and predicted inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on antibacterial activity of this class of compounds, thus simplifying design of new biologically active molecules.

RELATIONSHIP BETWEEN THE LIPOPHILICITY AND ANTIFUNGAL ACTIVITY OF SOME BENZIMIDAZOLE DERIVATIVES

2007 ◽  
Vol 06 (04) ◽  
pp. 687-698 ◽  
Author(s):  
SANJA PODUNAVAC-KUZMANOVIĆ ◽  
SINIŠA MARKOV ◽  
DIJANA BARNA
Keyword(s):  
Antifungal Activity ◽  
Predictive Ability ◽  
Quantitative Structure Activity Relationship ◽  
Benzimidazole Derivatives ◽  
Log P ◽  
Yeast Saccharomyces Cerevisiae ◽  
Software Products ◽  
Structure Activity ◽  
Lipophilicity Parameters

In the present paper, the antifungal activity of some 1-benzylbenzimidazole derivatives were evaluated against yeast Saccharomyces cerevisiae. The tested compounds displayed in vitro antifungal activity and minimum inhibitory concentration (MIC) was determined for all the compounds. Quantitative structure–activity relationship (QSAR) has been used to study the relationships between inhibitory activity and lipophilicity parameters ( log P). A variety of lipophilicity parameters ( log PHyper, CS log P, mi log P, A log P, IA log P, C log P, log PKow, and X log P) were calculated using different software products, and experimentally determined ("shake-flask" method). On the basis of correlations, the nonlinear structure–activity models were derived between the log 1/cMICand two different lipophilicity parameters. Four high-quality QSAR models were found to have a good predictive ability and a close agreement between the experimental and predicted values was obtained.

scholarly journals Correlation between the lipophilicity and antifungal activity of some benzoxazole derivatives

2010 ◽  
pp. 177-185 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Sonja Velimirovic
Keyword(s):  
Antifungal Activity ◽  
Inhibitory Concentration ◽  
Quantitative Relationship ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Biologically Active ◽  
High Agreement ◽  
Structure Activity ◽  
Lipophilicity Parameter ◽  
Office Software

In the present work, a quantitative relationship between the lipophilicity and antifungal activity of some benzoxazole derivatives against Candida albicans was investigated by using QSAR (quantitative structure-activity relationship) analyses. The descriptors which describe numerically the lipophilicity, logP, were calculated using Chem-Office Software version 7.0. The linear correlation between the minimal inhibitory concentration (log1/cMIC) and lipophilicity descriptors was investigated. The best QSAR model predicting the antifungal activity of the investigated series of benzoxazole was developed. The results are discussed on the basis of statistical data. High agreement between theoretical and experimental inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on antifungal activity of this class of compounds, which can be very useful in the design of new biologically active molecules.

scholarly journals QSAR modeling of antibacterial activity of some benzimidazole derivatives

2011 ◽  
Vol 17 (1) ◽  
pp. 33-38 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Dragoljub Cvetkovic
Keyword(s):  
Antibacterial Activity ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Structural Features ◽  
Benzimidazole Derivatives ◽  
Qsar Modeling ◽  
Qsar Study ◽  
Validation Procedure ◽  
Leave One Out

A quantitative structure-activity relationship (QSAR) study has been carried out for training set of 12 benzimidazole derivatives to correlate and predict the antibacterial activity of studied compounds against Gram-negative bacteria Pseudomonas aeruginosa. Multiple linear regression was used to select the descriptors and to generate the best prediction model that relates the structural features to inhibitory activity. The predictivity of the model was estimated by cross-validation with the leave-one-out method. Our results suggest a QSAR model based on the following descriptors: parameter of lipophilicity (logP) and hydration energy (HE). Good agreement between experimental and predicted inhibitory values, obtained in the validation procedure, indicated the good quality of the generated QSAR model.

scholarly journals Quantitative structure-activity relationship of some 1-benzylbenzimidazole derivatives as antifungal agents

2007 ◽  
pp. 139-147 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovic ◽  
Dijana Barna ◽  
Dragoljub Cvetkovic
Keyword(s):  
Antifungal Activity ◽  
Quantitative Structure Activity Relationship ◽  
Structure Activity Relationship ◽  
Biologically Active ◽  
Activity Relationship ◽  
Quantitative Structure ◽  
Yeast Saccharomyces Cerevisiae ◽  
Structure Activity ◽  
Lipophilicity Parameter

In the present study, the antifungal activity of some 1-benzylbenzimidazole derivatives against yeast Saccharomyces cerevisiae was investigated. The tested benzimidazoles displayed in vitro antifungal activity and minimum inhibitory concentration (MIC) was determined for all the compounds. Quantitative structure-activity relationship (QSAR) has been used to study the relationships between the antifungal activity and lipophilicity parameter, logP, calculated by using CS Chem-Office Software version 7.0. The results are discussed on the basis of statistical data. The best QSAR model for prediction of antifungal activity of the investigated series of benzimidazoles was developed. High agreement between experimental and predicted inhibitory values was obtained. The results of this study indicate that the lipophilicity parameter has a significant effect on antifungal activity of this class of compounds, which simplify design of new biologically active molecules.

scholarly journals Study of Calixarene Complexation with Biologically Active

2017 ◽  
Vol 5 (2) ◽  
pp. 49-55
Author(s):  
Olga Kalchenko ◽  
Sergiy Cherenok ◽  
Sergiy Suikov ◽  
Vitaly Kalchenko Vitaly Kalchenko
Keyword(s):  
Carboxylic Acids ◽  
Biologically Active ◽  
Log P ◽  
Cooh Group ◽  
Organic Solution ◽  
P Values ◽  
Rp Hplc ◽  
The Stability ◽  
Upper Rim ◽  
Modelling Methods

Host-Guest complexation of octakis(diphenoxyphosphoryloxy)tetramethylcalix[4]resorcinarene CRA and 5,17-bis-(N-tolyliminomethyl)-25,27-dipropoxycalix[4]arene CA with bio relevant aromatic, pyridine and diterpenoid carboxylic acids in water-organic solution had been studied by the RP HPLC and molecular modelling methods. The stability constants KA (387-1914 М-1) of the supramolecular complexes had been determined. It was shown the Host-Guest interactions are depended on structure of the Host molecules and log P values of the Guests. The complexation is determined by the hydrogen bonds of the COOH group of the carboxylic acids with P=O oxygen atom of diphenoxyphosphoryl group of the calixresorcinarene CRA, and oxygen or nitrogen atoms located on the lower or the upper rim of the calixarene CA.

scholarly journals Prediction of the inhibitory activity of benzimidazole derivatives against Bacillus spp.

2011 ◽  
pp. 251-261 ◽  
Author(s):  
Sanja Podunavac-Kuzmanovica ◽  
Dragoljub Cvetkovic ◽  
Slobodan Gadzuric
Keyword(s):  
Antibacterial Activity ◽  
Quantitative Structure Activity Relationship ◽  
Benzimidazole Derivatives ◽  
Calibration Model ◽  
Statistical Parameters ◽  
Gram Positive Bacteria ◽  
Bacillus Spp ◽  
In Vitro Antibacterial Activity ◽  
Leave One Out

In the present paper, the antibacterial activity of some 1-benzylbenzimidazole derivatives was evaluated against Gram-positive bacteria Bacillus spp. by using QSAR (quantitative structure-activity relationship). The tested compounds displayed in vitro antibacterial activity and minimum inhibitory concentration (MIC) was determined for all compounds. The lipophilicity descriptors of the studied compounds were measured by theoretical calculation (ClogP). The correlation between the MIC (log1/cMIC) and lipophilicity descriptors was investigated, and a mathematical model has been developed as a calibration model for predicting the antibacterial activity of this class of compounds. The quality of the model was validated by leave one out (LOO) technique as well as by the calculation of statistical parameters for the established model. The results of the present study may be useful for the designing of new benzimidazole derivatives that would be more potent against Bacillus spp.

scholarly journals Screening, Synthesis, and QSAR Research on Cinnamaldehyde-Amino Acid Schiff Base Compounds as Antibacterial Agents

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3027 ◽  
Author(s):  
Hui Wang ◽  
Mingyue Jiang ◽  
Fangli Sun ◽  
Shujun Li ◽  
Chung-Yun Hse ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Schiff Base ◽  
Amino Acid ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
New Drugs ◽  
Polarity Parameter ◽  
Qsar Models ◽  
New Compounds ◽  
Amino Acid Schiff Base

Development of new drugs is one of the solutions to fight against the existing antimicrobial resistance threat. Cinnamaldehyde-amino acid Schiff base compounds, are newly discovered compounds that exhibit good antibacterial activity against gram-positive and gram-negative bacteria. Quantitative structure–activity relationship (QSAR) methodology was applied to explore the correlation between antibacterial activity and compound structures. The two best QSAR models showed R2 = 0.9354, F = 57.96, and s2 = 0.0020 against Escherichia coli, and R2 = 0.8946, F = 33.94, and s2 = 0.0043 against Staphylococcus aureus. The model analysis showed that the antibacterial activity of cinnamaldehyde compounds was significantly affected by the polarity parameter/square distance and the minimum atomic state energy for an H atom. According to the best QSAR model, the screening, synthesis, and antibacterial activity of three cinnamaldehyde-amino acid Schiff compounds were reported. The experiment value of antibacterial activity demonstrated that the new compounds possessed excellent antibacterial activity that was comparable to that of ciprofloxacin.

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