Synthesis, In Silico Studies, Antimicrobial, Antioxidant Activities, Docking Simulation, and Computational Analysis of Novel Acrylamide Derivatives

New acrylamide compounds based on 4-aminoantipyrine were synthesized. 4-Acetaminoantipyrine was synthesized and its reactivity with salicylic aldehyde, vanillin, isovanillin and 5-methoxysalicylaldehyde with the formation of new N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)-3-(aryl)...

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Bibliographic Details
Published inRussian journal of general chemistry Vol. 94; no. 8; pp. 2044 - 2060
Main Authors Bayrak, H., Fahim, A. M., Boyraci, G. M., Karahalil, F. Y.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.08.2024
Springer Nature B.V
Subjects
Acrylamide
Aldehydes
Antioxidants
Aromatic compounds
Biological activity
Biological effects
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Molecular docking
Vanillin
DFT investigation
aminoantipyrine
acrylamide
molecular docking
antimicrobial activity
antioxidant activity
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Summary:New acrylamide compounds based on 4-aminoantipyrine were synthesized. 4-Acetaminoantipyrine was synthesized and its reactivity with salicylic aldehyde, vanillin, isovanillin and 5-methoxysalicylaldehyde with the formation of new N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)-3-(aryl)acrylamides was investigated. In addition, synthesized acrylamides were screened for ADME studies to elucidate their properties. The antimicrobial and antioxidant activitiy of the newly synthesized compounds were exceptionally high, surpassing the performance of the reference standard drug. Molecular docking simulations further confirmed these results, highlighting the heightened activity attributed to the substitute groups on the aromatic rings with different proteins and showed different interactions, confirming their biological evaluation. The optimization of target compounds using the DFT/B3LYP/6-311G(d) basis set demonstrated their stability and provided insights into their physical descriptors—Electrostatic Potential (ESP) and Molecular Electrostatic Potential (MEP). The analysis revealed both electrophilic and nucleophilic characters, showcasing their versatile binding capabilities in various pockets and confirming the biological results.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363224080188