Computational and theoretical chemistry of newly synthesized and characterized 2,2’-(5,5’-(1,4-phenylene)bis(1H-tetrazole-5,1-diyl))bis-N-acetamides

• Autores: Ejaz, Syeda Abida; Farid, Aftab; Zargar, Seema; Channar, Pervaiz Ali; Aziz, Mubashir; Wani, Tanveer A.; Attaullah, Hafiz Muhammad; Ujhan, Rabail; Tehzeeb, Arfa; Saeed, Aamer; Ali, Hafiz Saqib; Erben, Mauricio Federico
• Año de publicación: 2023
• Idioma: inglés
• Tipo de recurso: artículo
• Materia: ARYL COUPLING SYNTHONS; BIS-TETRAZOLE ACETAMIDES; DFT; ENERGETIC MATERIALS; SYNTHESIS; THERMODYNAMIC PROPERTIES
• Institución: Consejo Nacional de Investigaciones Científicas y Técnicas

Energetic heterocycles, including pyridines, triazoles, and tetrazoles, exhibit greater density, heats of formation, and oxygen balance compared to their carbocyclic counterparts, making them a promising approach for synthesizing novel bis-tetrazole acetamides. Synthesized compounds A-F, some of which feature a chlorine atom attached to the phenyl ring, serve as valuable synthons for aryl coupling reactions. Analysis via 1H-NMR and 13C-NMR spectroscopy, as well as density functional considerations through B3LYP functional correlation with 6-311 + + G(d) and 6-31G(d) basis set, revealed the observed LUMO/HOMO energies and charge transfer within the molecule. Additionally, the dipole moment, chemical hardness, softness, ionization potential, local reactivity potential via Fukui indices and thermodynamic properties (entropy, enthalpy, and Gibbs free energy) of the molecule were calculated through density functional theory studies. In addition, Molecular Docking studies were conducted to investigate the anti-cancer potential of synthesized heterocyclic compounds against caspase 3, NF-KAPPA-B and P53 protein. Molecular docking analysis demonstrated a potent interaction between 2,2’-(5,5’-(1,4-phenylene)bis(1H-tetrazole-5,1-diyl))bis-N-(2,4-dinitrophenyl) acetamides (6d) and TP53 and NF-KAPPA-B with binding energies of − 11.8 kJ/mol and − 10.9 kJ/mol for TP53 and NF-KAPPA-B, respectively. Similarly, 2,2’-(5,5’–(1,4-phenylene)bis(1H-tetrazole-5,1-diyl))bis-N-(2-chlorophenyl) acetamides (6f) exhibited a strong interaction with caspase-3 with binding energy of -10.0 kJ/mol, indicating their potential as therapeutic agents against these proteins. Furthermore, the findings of current study was further strengthen by 100 ns molecular dynamics (MD) simulations. Finally, theoretical studies of oxygen balance and nitrogen percentage suggest that these molecules can be utilized as energetic materials.
Fil: Ejaz, Syeda Abida. University of Bahawalpur; Pakistán
Fil: Farid, Aftab. Quaid-I-Azam University Islamabad; Pakistán
Fil: Zargar, Seema. King Saud University; Arabia Saudita
Fil: Channar, Pervaiz Ali. Dawood University of Engineering and Technology Karachi; Pakistán
Fil: Aziz, Mubashir. The Islamia University of Bahawalpur; Pakistán
Fil: Wani, Tanveer A.. King Saud University; Arabia Saudita
Fil: Attaullah, Hafiz Muhammad. King Saud University; Arabia Saudita
Fil: Ujhan, Rabail. University of Sindh; Pakistán
Fil: Tehzeeb, Arfa. Quaid-I-Azam University Islamabad; Pakistán
Fil: Saeed, Aamer. Quaid-I-Azam University Islamabad; Pakistán
Fil: Ali, Hafiz Saqib. University of Manchester; Reino Unido
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina