Carbonic anhydrase inhibition of Schiff base derivative of imino-methyl-naphthalen-2-ol: Synthesis, structure elucidation, molecular docking, dynamic simulation and density functional theory calculations

• Published in: Journal of molecular structure 2018-03, Vol.1156, p.193-200
• Main Authors: Abbas, Saghir, Nasir, Hafiza Huma, Zaib, Sumera, Ali, Saqib, Mahmood, Tariq, Ayub, Khurshid, Tahir, Muhammad Nawaz, Iqbal, Jamshed
• Format: Article
• Language: English
• Subjects: Density functional theory; Molecular dynamic simulations; Physicochemical properties; X-ray diffraction
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.11.086

In the present study, we have designed and synthesized a Schiff base derivative 3 and characterized by FT-IR, 1H and 13C NMR spectroscopy. Single crystal X-ray diffraction and NMR studies were also performed. The synthetic compound was screened for its inhibitory potential against carbonic anhydrase II. The experimental results were validated by molecular docking and dynamic simulations of compound 3 in the active pocket of enzyme. Important binding interactions with the key residues in the active site of the carbonic anhydrase enzyme were revealed. Moreover, supramolecular assembly of the title compound was analyzed by density functional theory (DFT) calculations. These studies rendered a more clear understanding for the demonstration of novel molecular mechanism involved in CA II inhibition by the synthesized compound. [Display omitted] •Design and synthesis of Schiff base derivative.•Characterization by FT-IR, 1H and 13C NMR spectroscopy.•Single crystal X-ray diffraction and NMR studies were performed.•The synthetic compound was active against carbonic anhydrase II.•Molecular docking and dynamic simulations studies were carried out.