Piperazine-azole-fluoroquinolone hybrids: Conventional and microwave irradiated synthesis,biological activity screening and molecular docking studies |
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Institution: | 1. Karadeniz Technical University, Department of Chemistry 61080 Trabzon, Turkey;2. Recep Tayyip Erdogan University, Department of Chemistry, 53100 Rize, Turkey;3. Dept. of Biotechnology, School of Bio-Sciences and Technology, VIT, Vellore 632014, India;1. Department of Chemistry, The Oxford College of Engineering, Bangalore (Karnataka) -560068, India;2. Department of Chemistry, Regional Ayurveda Research Institute for Drug Development, Gwalior (M.P.) – 474009, India;3. Department of Biotechnology, Lovely Professional University, Jalandhar (Punjab) – 144111, India;4. Regional Advanced Water Testing Laboratory, Mohali (Punjab) -160059, India;5. Punjab Biotechnology Incubators, Mohali (Punjab) -160059, India;1. Academy of Advanced Interdisciplinary Studies, Qilu University of Technology (Shandong Academy of Sciences), Jinan, PR China;2. School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan, PR China;3. Department of Medical Imaging, Jinling Hospital, Medical School of Nanjing University, Nanjing, PR China;4. State Key Laboratory of Biobased Material and Green Papermaking (LBMP), Qilu University of Technology (Shandong Academy of Sciences), Jinan, PR China;1. Institute of Pharmaceutical Sciences, Kurukshetra University, Kurukshetra, 136119, India;2. Institute of Pharmaceutical Sciences, Guru Ghasidas University, Bilaspur, 495009, India;3. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India;4. Biorefining and Advanced Materials Research Center, Scotland''s Rural College (SRUC), Kings Buildings, Edinburgh, EH9 3JG, UK;1. Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University, Minia 61519, Egypt;2. Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA;1. Chemistry Department, Faculty of Science, Minia University, 61519, El-Minia, Egypt;2. Department of Organic Pharmacy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Egypt |
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Abstract: | A series of new 1,2,4-triazole and 1,3,4-oxadiazole derivatives was obtained via several steps sequential reactions of phenyl piperazine. Then, these compounds were converted to the corresponding fluoroquinolone hybrids via one pot three component Mannich reaction. All the reactions were examined under conventional and microwave mediated conditions, and optimum conditions were determined. The effect of different solvents and microwave power on microwave prompted reactions was investigated as well. All the newly synthesized compounds were characterized by FTIR, 1H NMR, 13C NMR and EI MS spectral techniques. The antimicrobial activity, DNA gyrase and Topoisomerase IV inhibition potentials were performed. The results obtained showed that fluoroquinolone hybrids possess good antimicrobial activity. Moreover, Fluoroquinolone-azole-piperazine hybrids synthesized in the present study displayed excellent DNA gyrase inhibition. To unveil the interaction mode of compounds to receptor, a molecular docking study was performed. With an average least binding energy of ?9.5 kcal/mol, all compounds were found to have remarkable inhibitory potentials against DNA gyrase (E. coli). |
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Keywords: | Fluoroquinolone 1 2 4-triazole Microwave irradiation Antimicrobial activity DNA gyrase Topoisomerase IV Molecular docking |
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