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Synthesis and quantitative structure activity relationship (QSAR) of arylidene (benzimidazol-1-yl)acetohydrazones as potential antibacterial agents

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Abstract

Ethyl (benzimidazol-1-yl)acetate was subjected to hydrazinolysis with hydrazine hydrate to give (benzimidazol-1-yl)acetohydrazide. The latter was reacted with various aromatic aldehydes to give the respective arylidene (1H-benzimidazol-1-yl)acetohydrazones. Solutions of the prepared hydrazones were found to contain two geometric isomers. Similarly (2-methyl-benzimidazol-1-yl)acetohydrazide was reacted with various aldehydes to give the corresponding hydrazones. The antibacterial activity was evaluated in vitro by minimum inhibitory concentration (MIC) against Agrobacterium tumefaciens (A. tumefaciens), Erwinia carotovora (E. carotovora), Corynebacterium fascians (C. fascians) and Pseudomonas solanacearum (P. solanacearum). MIC result demonstrated that salicylaldehyde(1H-benzimidazol-1-yl)acetohydrazone (4) was the most active compound (MIC = 20, 35, 25 and 30 mg/L against A. tumefaciens, C. fascians, E. carotovora and P. solanacearum, respectively). Quantitative structure activity relationship (QSAR) investigation using Hansch analysis was applied to find out the correlation between antibacterial activity and physicochemical properties. Various physicochemical descriptors and experimentally determined MIC values for different microorganisms were used as independent and dependent variables, respectively. pMICs of the compounds exhibited good correlation (r = 0.983, 0.914, 0.960 and 0.958 for A. tumefaciens, C. fascians, E. carotovora and P. solanacearum, respectively) with the prediction made by the model. QSAR study revealed that the hydrophobic parameter (ClogP), the aqueous solubility (LogS), calculated molar refractivity, topological polar surface area and hydrogen bond acceptor were found to have overall significant correlation with antibacterial activity. The statistical results of training set, correlation coefficient (r and r 2), the ratio between regression and residual variances (f, Fisher’s statistic), the standard error of estimates and significant (s) gave reliability to the prediction of molecules with activity using QSAR models. However, QSAR equations derived for the MIC values against the tested bacteria showed negative contribution of molecular mass.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Mekkah, Kingdom of Saudi Arabia

    Yeldez El-Kilany, Nariman M. Nahas & Mariam A. Al-Ghamdi

  2. Department of Pesticide Chemistry and Technology, Faculty of Agriculture, Alexandria University, El-Shatby, Alexandria, 21545, Egypt

    Mohamed E. I. Badawy

  3. Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt

    El Sayed H. El Ashry

Authors
  1. Yeldez El-Kilany
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  2. Nariman M. Nahas
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  3. Mariam A. Al-Ghamdi
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  4. Mohamed E. I. Badawy
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  5. El Sayed H. El Ashry
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Correspondence to Mohamed E. I. Badawy.

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El-Kilany, Y., Nahas, N.M., Al-Ghamdi, M.A. et al. Synthesis and quantitative structure activity relationship (QSAR) of arylidene (benzimidazol-1-yl)acetohydrazones as potential antibacterial agents. World J Microbiol Biotechnol 31, 145–152 (2015). https://doi.org/10.1007/s11274-014-1755-4

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  • DOI: https://doi.org/10.1007/s11274-014-1755-4

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