Construction,molecular docking,antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole |
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| Institution: | 1. Chemistry Department, College of Science, Jouf University, P. O. Box 2014, Sakaka, Aljouf, Saudi Arabia;2. Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt;3. Department of Pharmaceutics, College of Pharmacy, Jouf University, Sakaka, AlJouf, Saudi Arabia;4. Department of Microbiology and Immunology, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;5. Clinical laboratory sciences Department, College of Applied Medical Sciences, Jouf University, Sakaka, Saudi Arabia;6. Medical Biochemistry Department, Faculty of Medicine, Tanta University, Tanta, Egypt;7. Department of Chemistry, Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, 44000 Pakistan |
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| Abstract: | This dissertation presents a method for the synthesis of substituted indoles bearing heterocyclic substituent in the 3- position. The route for the synthesis of the heterocyclic substituents indoles starts from the 3-acetyl indole nucleus. The reaction of 3-acetyl indole 1 with hydrazide compounds such as phenylhydrazine, hydrazine hydrate, and thio-semicarbazide, yields 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2, 3-(1-hydrazonoethyl)-1H-indole 6, and thiosemicarbazone 10, respectively. Thiophene-2-carboxaldeyde, isatine and 3-acetyl indole reacted with 3-(1-Hydrazonoethyl)-1H-indole 6. In the same way, 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2 reacted with thioglycollic acid, glycine and benzaldehyde. Thiosemicarbazone 10 reacted smoothly with acetic anhydride, piperidine, concentration of hydrochloric acid and thiophene-2-carboxaldeyde to provide the corresponding heterocycles. The reaction of 3-acetyl indole 1 with amine compounds such as p-nitroaniline formed Schiff base 15, which reacted with thioglycollic acid to give compound 16. 3-Acetyl indole 1 reacted with ethylene diamine to afford bis imine indole 17. The reports of the docking study revealed that the new compounds exhibit good antibacterial activity. The synthesized compounds screened in vitro for their antibacterial activity revealed remarkable inhibitory effects on the selected microorganisms. Besides, the antioxidant activity of some newly designed compounds has been investigated. The structures of the newly synthesized compounds are examined by spectral data (IR, 1HNMR, 13C NMR and mass spectra). |
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| Keywords: | 3-Acetyl indole Biological evaluations Molecular docking Thioglycollic acid Ethylene diamine and hydrazine hydrate |
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