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

Abstract

In spite of phenobarbital has been used in various medical fields as hypnotics, anxiolytics, and anticonvulsants, it also contains active functional groups that can be reacted to form other products as 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 1,2,3,4Tetrazoline moiety 7, 8 (a-c) were prepared by cycloaddition reaction between different Schiff bases derivatives and sodium azide. The compounds were characterized by Melting point, 13 C-NMR, 1 H-NMR and FTIR techniques. Also, the result compounds were tested against two kinds of bacteria and two kinds of fungi. Most of the prepared derivatives were showed 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 with Molegro Virtual Docker (MVD).

Ephedra alte extracts' GC-MS profiles and antimicrobial activity against multidrug-resistant pathogens (MRSA)

“…In the present work, the GC-MS analysis of E. alte extract ( Table 2 ) confirmed that the extract contains several antimicrobial compounds such as D-glucopyranoside derivatives (30.8% of the total components) and phenobarbital derivatives (16.8% of the total components). Kawsar et al (2018) [ 32 ] and Fahad et al (2021) [ 33 ] reported that D-glucopyranoside and phenobarbital derivatives have the ability to inhibit many bacteria and fungi. The chemical analysis in Table 2 showed that 0.5% of the chemical compositions of the extract were propanediols.…”

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“…Not only the small molecules, but also complexes and larger molecules are suitable to be investigated by employing such types of DFT calculations [69][70][71][72]. Especially in the case of exploring impacts of environments on molecular properties, such DFT evaluated features could help to learn more details [73][74][75]. The materials, graphical representations, and obtained results of this work were exhibited in Figures 1 and 2 and Tables 1 and 2 to be discussed for assessing Vit-B3 in 1-octanol and water solvent environments.…”

Potential inhibitory activity of phytoconstituents against black fungus: In silico ADMET, molecular docking and MD simulation studies

“…Considering literature data, many active agents against fungal infections have been documented in the herbal medicine. The natural products comprising of a diverse range of secondary metabolites including flavonoids, coumarins, limonoids, terpenoids, phenolic compounds, tannins, quinones, saponins, xanthones, alkaloids, peptides, and biosurfactants were reported having in vitro antifungal properties [36] , [37] , [38] , [39] , [40] , [41] , [42] , [43] , [44] , [45] . Therefore, in recent year research on these phytochemicals and their derived compounds have been the subject of increased investigation due to their importance in drug design.…”