Synthesis, Molecular Docking Study, and Molecular Dynamics Simulation of New 1,3-Dimethyl-5-methylidenebarbituric Acid Derivatives Prepared by Cyclobutane Cleavage.

Autor: Al-Ghorbani, M., Sweidan, K., Krefeh, H. A., Joshi, R., Ramu, R., AlDamen, M.
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Zdroj: Russian Journal of Organic Chemistry; Mar2023, Vol. 59 Issue 3, p445-454, 10p
Abstrakt: Various organic derivatives of 1,3-dimethylbarbituric acid attract widespread interest as biologically active compounds, medicinal agents, and precursors in organic synthesis. The chemical reactivity of the cyclobutane moiety in 1,3-dimethyl-5-methylidenebarbituric acid dimer (2) was examined at room temperature toward various primary aliphatic amines (benzylamine, 4-methoxybenzylamine, and 3-fluorobenzylamine) and hydroxide ion, as well as in acidic medium. New compounds were prepared by ring-opening of the cyclobutane moiety via nucleophile attack on the exocyclic methylene group. The structures of the synthesized compounds were elucidated by employing 1H and 13C NMR (including DEPT) and mass spectrometric techniques. Molecular docking revealed a high binding affinity (–9.0 kcal/mol) of one of the obtained compounds (6). In addition, the molecular dynamics simulation and binding free energy calculation data confirmed that compound 6 is the most stable among the others. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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