Construction, molecular docking, antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole

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).