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As Antimicrobial Agents: Synthesis, Structural Characterization and Molecular Docking Studies of Barbituric Acid Derivatives from Phenobarbital

Journal: Chemical Methodologies (Vol.6, No. 2)

Publication Date:

Authors : ; ; ; ;

Page : 122-136

Keywords : Barbituric acid; Phenobarbital; Cycloaddition reaction; tetrazoline; tetrazole;

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Abstract

Despite phenobarbital having been used in various medical fields as hypnotics, anxiolytics, and anticonvulsants, it also contains active functional groups that can form dyes, polymers, antimicrobial, and anti-antioxidants agents. A series of barbituric acid derivatives containing 1,2,3,4-tetrazoline moiety were synthesized from phenobarbital. Phenobarbital 1 as raw starting material was reacted with acrylonitrile compound to give diacetonitrile derivative 2, this compound was treated in two ways, urea and thiourea to form barbituric acid derivatives containing oxadiazole and thiadiazole ring 3, 4 respectively. The Schiff bases derivatives 5, 6(a-c) were synthesized from reacting the latter compounds with three aromatic aldehydes. In the final step, the barbituric acid derivatives containing 1,2,3,4-tetrazoline moiety 7, 8(a-c) were prepared by cycloaddition reaction between different Schiff bases derivatives and sodium azide. The synthesized compounds were characterized using melting point, 13C-NMR, 1H-NMR and FTIR techniques. The compounds were also tested against two kinds of bacteria and two kinds of fungi. Most of the prepared derivatives revealed a high and clear effect against different types of bacteria and fungi. Molecular docking of final barbituric acid derivatives 7, 8(a, b) were investigated using Molegro Virtual Docker (MVD).

Last modified: 2022-01-03 05:53:12