Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine.

The data on the synthesis of N-aminomorpholine hydrazones are presented. It is shown that the interaction of N-aminomorpholine with functionally substituted benzaldehydes and 4-pyridinaldehyde in isopropyl alcohol leads to the formation of corresponding hydrazones. The structure of the synthesized compounds was studied by 1 H and 13 C NMR spectroscopy methods, including the COSY ( 1 H- 1 H), HMQC ( 1 H- 13 C) and HMBC ( 1 H- 13 C) methodologies. The values of chemical shifts, multiplicity, and integral intensity of 1 H and 13 C signals in one-dimensional NMR spectra were determined. The COSY ( 1 H- 1 H), HMQC ( 1 H- 13 C), and HMBC ( 1 H- 13 C) results revealed homo- and heteronuclear interactions, confirming the structure of the studied compounds. The antiviral, cytotoxic, and antimicrobial activity of some synthesized hydrazones were investigated. It is shown that 2-((morpholinoimino)methyl)benzoic acid has a pronounced viral inhibitory property, comparable in its activity to commercial drugs Tamiflu and Remantadine. A docking study was performed using the influenza virus protein models (1930 Swine H1 Hemagglutinin and Neuraminidase of 1918 H1N1 strain). The potential binding sites that are complementary with 2-((morpholinoimino)methyl)benzoic acid were found.