Synthesis, Biological Activitiy and DFT Study of New Azaphenalene Derivatives

Abstract

In this study, synthesis, biological activitiy and DFT properties of azaphenalene derivatives will be investigated. Consequently, n-benzoyl-1,3 diaryl-2(para formyl) azaphenalene derivatives were synthesized via an irreversible unilateral condensation reaction of the aromatic dial, the 2,7-naphthalene diol, carboxylic acids, and NH3 (aq) (25%). An aliphatic and aromatic carboxylic acid and an aromatic dial were used in this multicomponent reaction, and good yields were obtained for the products. The method is quick and easy without solvents, and the reaction takes place in a short amount of time, this type of reaction is precessed by a Betti reaction. Pseudomonas and Staphylococcus saprophyticus were used as Gram-positive and Gram-negative bacteria susceptible to the antimicrobial activity of azaphenalene derivatives. The resulting antimicrobial activity was moderate to good. Comparing other synthesized compounds, compound 5j showed the strongest inhibition against Staphylococcus saprophyticus. Compounds 5c, 5f, 5e, and 5i also demonstrated good inhibition against Pseudomonas aeruginosa, while other synthesized compounds showed moderate inhibition. Analyses of the density functional theory (DFT) of azaphenalene derivatives in the gas phase were performed at the B3LYP/6-31G* level of theory and the results were compared with the experimental value. Calculations included thermodynamic parameters, electronic properties, frontier analysis, and molecular electrostatic potential (MEP). The DFT results agree with the experimental results, indicating that all azaphenalene derivatives are in stable vibrational states. A comparison of experimental and frontier analyses revealed a good agreement.