Title of article :
Crystal structure, Hirshfeld analysis and a molecular docking study of a new inhibitor of the Hepatitis B virus (HBV): ethyl 5-methyl-1,1-dioxo-2-{[5-(pentan-3-yl)-1,2,4-oxadiazol-3-yl]methyl}-2H-1,2,6-thiadiazine-4-carboxylate
Author/Authors :
Ivachtchenko, Alexandre V. ChemRar Research and Development Institute, Russian Federation , Kovalenko, Sergiy M. ChemRar Research and Development Institute, Russian Federation , Kravchenko, Dmitry V. Chemical Diversity Research Institute, Russian Federation , Mitkin, Oleg D. ChemRar Research and Development Institute, Russian Federation , Ivanov, Vladimir V. V.N. Karazin Kharkiv National University, Ukraine , Langer, Thierry University of Vienna, Austria
Abstract :
The title compound, C15H22N4O5S, was prepared via alkylation of 3-(chloromethyl)-5-(pentan-3-yl)-1,2,4-oxadiazole in anhydrous dioxane in the presence of triethylamine. The thiadiazine ring has an envelope conformation with the S atom displaced by 0.4883 (6) Å from the mean plane through the other five atoms. The planar 1,2,4-oxadiazole ring is inclined to the mean plane of the thiadiazine ring by 77.45 (11)°. In the crystal, molecules are linked by C—H⋯N hydrogen bonds, forming chains propagating along the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots have been used to analyse the intermolecular contacts present in the crystal. Molecular docking studies were use to evaluate the title compound as a potential system that interacts effectively with the capsid of the Hepatitis B virus (HBV), supported by an experimental in vitro HBV replication model.
Keywords :
crystal structure , 2H-1,2,6-thiadiazine 1,1-dioxide , hepatitis B , HBV , hydrogen bonding , Hirshfeld surface analysis , molecular docking study
Journal title :
Acta Crystallographica Section E: Crystallographic Communications