Schiff base of isoniazid and ketoprofen: synthesis, X-ray crystallographic, spectroscopic, antioxidant, and computational studies

Authors : Naima REHMAN, Muhammad KHALID, Moazzam Hussain BHATTI, Uzma YUNUS, Ataualpa Albert Carmo BRAGA, Faiz AHMED, Syed Muddassir Ali MASHHADI, Muhammad Nawaz TAHIR

Pages : 639-651

View : 15 | Download : 4

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Ketoprofen and isoniazid together are a potential combination of a nonsteroidal antiinflammatory drug and an antitubercular medicine to treat tuberculosis and associated symptoms like fever and fatigue. The Schiff base of isoniazid with ketoprofen is synthesized in this research. Infrared spectroscopy insert ignore into journalissuearticles values(IR); and X-ray diffraction insert ignore into journalissuearticles values(XRD); analysis of the crystal packing proved the formation of the Schiff base and the existence of N-H$\cdot \cdot \cdot $O hydrogen bonds between the hydrogen-bonded dimer of the Schiff base. The complete geometrical optimization of the monomer and hydrogen-bonded dimer of the Schiff base is performed utilizing M06-2X/6-31Ginsert ignore into journalissuearticles values(d,p); level theory and compared with the experimental data to optimize the molecular structure. The effect of 2,2-diphenyl-1-picrylhydrazyl insert ignore into journalissuearticles values(DPPH); radical scavenging activity shows that the synthesized Schiff base has improved antioxidant activity. Molecular docking studies against Mycobacterium tuberculosis insert ignore into journalissuearticles values(Mtb); RNA polymerase-related targets with PDB codes 2M6O and 4KBJ and lung surfactant protein A insert ignore into journalissuearticles values(SP-A); with PDB ID 5FFT suggest that it can be screened as a potent drug against Mtb infection of the lungs. Frontier orbital theory analysis shows a high energy gap between the HOMO and LUMO, which suggests that the reported Schiff base might be a bioactive compound. Different experimental insert ignore into journalissuearticles values(XRD, IR, thermal gravimetric analysis, differential scanning calorimetry); and computational studies correlate and validate findings related to this novel Schiff base.
Keywords : Isoniazid and ketoprofen Schiff base, X ray diffraction, density functional theory studies, molecular docking, free radical scavenging activity