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Int. J. Mol. Sci. 2014, 15(3), 5115-5127; doi:10.3390/ijms15035115
Article

Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site

1,* , 1
, 1,2
, 1
, 3
, 4
, 5
 and 6
1 Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia 2 Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia 21321, Alexandria, Egypt 3 Department of Chemistry, College of Sciences, Hail University, P. O. Box 2440, Hail 81451, Saudi Arabia 4 LCAE, Faculté des Sciences, Université Mohammed Premier, Oujda BP 717 60000, Morocco 5 Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan 6 Laboratoire Chimie Matériaux, Faculté Sciences, Université Mohammed Premier, Oujda BP 717 60000, Morocco
* Author to whom correspondence should be addressed.
Received: 11 December 2013 / Revised: 28 February 2014 / Accepted: 5 March 2014 / Published: 21 March 2014
(This article belongs to the Section Bioinorganic Chemistry)
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Abstract

A series of new 2-aminobenzamide derivatives (110) has been synthesized in good to excellent yields by adopting both conventional and/or a time-efficient microwave assisted methodologies starting from isatoic anhydride (ISA) and characterized on the basis of their physical, spectral and microanalytical data. Selected compounds of this series were then tested against various bacterial (Bacillus subtilis (RCMB 000107) and Staphylococcus aureus (RCMB 000106). Pseudomonas aeruginosa (RCMB 000102) and Escherichia coli (RCMB 000103) and fungal strains (Saccharomyces cerevisiae (RCMB 006002), Aspergillus fumigatus (RCMB 002003) and Candida albicans (RCMB 005002) to explore their potential as antimicrobial agents. Compound 5 was found to be the most active compound among those tested, which showed excellent antifungal activity against Aspergillus fumigatus (RCMB 002003) more potent than standard Clotrimazole, and moderate to good antibacterial and antifungal activity against most of the other strains of bacteria and fungi. Furthermore, potential pharmacophore sites were identified and their activity was related with the structures in the solution.
Keywords: isatoic anhydride; conventional method; microwave method; 2-aminobenzamide; antimicrobial activity isatoic anhydride; conventional method; microwave method; 2-aminobenzamide; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Mabkhot, Y.N.; Al-Majid, A.M.; Barakat, A.; Al-Showiman, S.S.; Al-Har, M.S.; Radi, S.; Naseer, M.M.; Hadda, T.B. Synthesis and Biological Evaluation of 2-Aminobenzamide Derivatives as Antimicrobial Agents: Opening/Closing Pharmacophore Site. Int. J. Mol. Sci. 2014, 15, 5115-5127.

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