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Benzimidazol-1-yl-1-phenylpropanone Analogs as Potent Antimicrobial Agents: Rational Design and Synthesis |
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| Authors: | Prof. Ritchu Babbar Dr. Swikriti Makkar Dr. Deepika Saini Dr. Ravi Rawat Dr. Celia Vargas-De-La-Cruz Dr. Faris Q. Alenzi Prof. Tapan Behl |
| Affiliation: | 1. Chitkara College of Pharmacy, Chitkara University, Rajpura, Distt., Patiala, 140401 India;2. Chitkara College of Pharmacy, Chitkara University, Rajpura, Distt., Patiala, 140401 India Department of Pharmaceutical Chemistry, Akal College of Pharmacy and Technical Education, Mastuana Sahib, Sangrur, 148001 India;3. Lloyd Institute of Management and Technology, Plot No. 11, Knowledge Park-II, Greater Noida, 201306 India;4. School of Health Sciences & Technology, UPES University, Bidholi, 248007 Dehradun, India;5. Department of Pharmacology, Bromatology and Toxicology, Faculty of Pharmacy and Biochemistry, Universidad Nacional Mayor de San Marcos, Lima, 150001 Peru E-Health Research Center, Universidad de Ciencias y Humanidades, Lima, 15001 Peru;6. Department of Medical Laboratory Sciences, College of Applied Medical Sciences, Prince Sattam Bin Abdulaziz University, Al-Kharj, 11942 Saudi Arabia |
| Abstract: | Designed, synthesized a sequence of novel benzimidazol-1-yl-1-phenylpropanone hybrids and assessed for in vitro antimicrobial potential counter to several bacterial strains. Computational Methodology was carried out for designing of the target molecules and structures were confirmed by spectroscopic analysis. Amid the 12 integrated derivatives, (3-(2-((3-fluorobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6g ) and 3-(2-((4-fluorobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6k ) were found to acquire excellent antibacterial activity against all bacterial strains (Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus), whereas derivative 3-(2-((2-fluorobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6c ), was potent against Escherichia coli, Bacillus subtilis, Staphylococcus aureus and displayed moderate action against P. aeruginosa. Derivatives with NO2 substituent at 3rd and 4th position, 3-(2-((3-nitroobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6h ) and 3-(2-((4-nitroobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6 l ) respectively declared good to moderate results against all bacterial strains. Further, 3-(2-((3-chlorobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6f ) and 3-(2-((4-chlorobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one ( 6j ) were found to be more competent against both fungal strains (C. albicans, A. niger). Serial two-fold dilution method was used for the entire study and standard drugs utilized were ciprofloxacin and clotrimazole. MIC values (μg/ml) of novel synthesized analogs were reported in comparison to standard drugs for antibacterial and antifungal actions. Molecular docking studies showed that designed molecules dynamically bound with effective area of the receptor (DNA gyrase B, Clotrimazole complex of cytochrome P 45046A1) and in vitro results were in accord with in silico studies. |
| Keywords: | benzimidazole Mannich base molecular docking studies antibacterial activity antifungal activity |