Synthesis, spectroscopic, computational and molecular docking studies of 1-(pyridin-2-yl amino)methyl napthalene-2-ol

Autor: Mani Jeeva, V. Vijayakumar, P. Rajamani, Maria Susai Boobalan, N. Sundaraganesan
Rok vydání: 2019
Předmět:
Zdroj: Journal of Molecular Structure. 1197:417-429
ISSN: 0022-2860
DOI: 10.1016/j.molstruc.2019.07.040
Popis: A simple Mannich condensation reaction furnished 1-(pyridin-2-yl amino)methyl napthalene-2-ol using 2-aminopyridine, naphthalene-2-ol and formaldehyde as starting materials. Then, a complete spectroscopic documentation of synthesized compound was carried out using analytical techniques such as FT-IR, UV-Visible, 1H and 13C NMR, HR-MS, FT-Raman and TG/DSC analysis. DFT calculations were also performed in order to obtain a reliable structural information in concurrence with experimental results. Geometry optimization suggested a planar N-atom at position-32 due to its lone pair delocalization which would make it less basic. The vibrational analysis data showed a sufficient evidence for the possible existence of inter-molecular H-bonding interactions through naphthalene –OH group. Moreover, the TG/DSC curve showed drying temperature range between 100 and 150 °C for the title compound. In addition, molecular docking studies were also carried out and suggested that the target molecule, 1-(pyridin-2-yl amino)methyl-napthalene-2-ol, had the ability to bind more efficiently with anti-microbial ciprofloxacin, on the protein surface through an extensive H-bonding interaction with a very low inhibition concentration of only about 76.08 μM.
Databáze: OpenAIRE
Externí odkaz: