Relationship Between the Lipophilicity and Antifungal Activity of Some Benzimidazole Derivatives

Abstract

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.

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

“…The synthesis of benzimidazoles has received a lot of attention owing to the varied biological activity exhibited by a number of these compounds. [1][2][3][4][5][6][7] This class of molecules proved to be very important, as they possess pharmaceutical properties, including antibacterial, against different strains of Gram-positive and Gram-negative bacteria, 8-10 antifungal 3 and herbicidal 11 activity. It is also well-known that these molecules are present in a variety of analgesic, 12 anti-oxidant, 13,14 anti-allergic 15,16 and antitumoral 17 agents.…”

Antibacterial activity of cobalt(II) complexes with some benzimidazole derivatives

“…[1][2][3][4][5][6][7] This class of compounds has been found to show antimicrobial activities against Gram-positive and Gram-negative bacteria, primarily because of the potential bio-activity of benzimidazole--based ligands. [8][9][10] Hence, the incorporation of imidazole and benzimidazole nuclei is an important synthetic strategy in drug discovery.…”

QSAR modeling of antibacterial activity of some benzimidazole derivatives

“…Using QSAR, an estimate of the activity of a chemical from its molecular structure can be obtained; QSAR offers the possibility for screening a large number of chemicals in a short time and at low cost [4][5][6][7].…”

“…The position and type of the substituents on the benzimidazole ring are responsible for the variety of biological activities. Many derivatives of benzimidazole are well known as antibacterial agents, as well as this class of compounds have been found to show antimicrobial activities against Gram-positive and Gramnegative bacteria, primarily because of the potential bio-activity of benzimidazole-based ligands [8][9][10][11][12][13][14][15][16][17][18][19]. So, the incorporation of the imidazole and benzimidazole nuclei is an important synthetic strategy in drug discovery.…”

“…In view of the above and in continuation of our studies on inhibitory activities of benzimidazole derivatives [4][5][6][7], [11][12][13][14][15][16][17][18], as well as on correlation of molecular properties with activity, the objective of this investigation was to study the usefulness of QSAR in the prediction of the antibacterial activity of benzimidazole derivatives against Gram-negative bacteria Pseudomonas aeruginosa. The multiple linear regression (MLR) models have been developed as mathematical equations which relate chemical structure to the inhibitory activity.…”