Add time:08/27/2019         Source:sciencedirect.com

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.

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