Abstract
New derivatives of lupinine are of great interest in the search for new antiviral substances, which is a pressing issue in modern medicine. The aim of the study was the chemical development of a potentially biologically active substance based on 1,2,3-triazole derivative of lupinine and the development of a technological scheme for its production. Results. The results of studies on the synthesis and structural features of a new, previously undescribed 1,4-disubstituted 1H-1,2,3-triazole derivative of lupinyl azide are presented. For the first time, a method for obtaining the substance of the triazole derivative of lupinine was carried out, and on its basis, a technology for its production was developed. Chemical modification of lupininyl azide was carried out at the azide group in position C-1 of the quinolizine backbone. It was established that when interacting with lupininyl azide and a functionally substituted alkyne in the presence of CuSO4 and sodium ascorbate in a dimethylformamide solution, the corresponding 4-substituted {1-[((1S,9aR)-octahydro-2H-quinolizin-1-yl)methyl]-1H-1,2,3-triazol-4-yl}methyl-3-tert-butyl-2-hydroxy-5-ethylbenzoate can be formed. The structure of the synthesized compound was established based on the analysis of IR- and UV-spectroscopy spectra, as well as 1H and 13C NMR spectra; the multiplicity of signals in the 13C NMR spectra was determined from spectra recorded in the J-modulation mode (JMOD). Conclusion. For the first time, a triazole derivative of lupinine was obtained using chemical modification, a production technology was developed, and the quality indicators of the substance were determined. The physicochemical properties and structural features of the synthesized compound were established based on physicochemical methods. The ability of the synthesized compound {1-[((1S,9aR)-octahydro-2H-quinolizin-1-yl)methyl]-1H-1,2,3-triazol-4-yl}methyl-3-tert-butyl-2-hydroxy-5-ethylbenzoate to reduce the infectivity of the virus when processing virus-containing material was established, which indicated the prospects for studying this sample as a virucidal agent affecting extracellular virions.