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
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 f...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020-01-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019015986 |
| _version_ | 1818941291375886336 |
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| author | Alexandre V. Ivachtchenko Sergiy M. Kovalenko Dmitry V. Kravchenko Oleg D. Mitkin Vladimir V. Ivanov Thierry Langer |
| author_facet | Alexandre V. Ivachtchenko Sergiy M. Kovalenko Dmitry V. Kravchenko Oleg D. Mitkin Vladimir V. Ivanov Thierry Langer |
| author_sort | Alexandre V. Ivachtchenko |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-20T06:53:12Z |
| format | Article |
| id | doaj.art-2d9eab74010f4535842a0f89b10e00a2 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T06:53:12Z |
| publishDate | 2020-01-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-2d9eab74010f4535842a0f89b10e00a22022-12-21T19:49:26ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-01-01761121710.1107/S2056989019015986su5529Crystal 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-carboxylateAlexandre V. Ivachtchenko0Sergiy M. Kovalenko1Dmitry V. Kravchenko2Oleg D. Mitkin3Vladimir V. Ivanov4Thierry Langer5ChemRar Research and Development Institute, 7 Nobel St, Innovation Center, Skolkovo Territory, Moscow, 143026, Russian FederationChemRar Research and Development Institute, 7 Nobel St, Innovation Center, Skolkovo Territory, Moscow, 143026, Russian FederationChemical Diversity Research Institute, 2A Rabochaya St, Khimki, Moscow Region, 141400, Russian FederationChemRar Research and Development Institute, 7 Nobel St, Innovation Center, Skolkovo Territory, Moscow, 143026, Russian FederationV.N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, UkraineUniversity of Vienna, Althanstrasse 14, A-1090, Vienna, AustriaThe 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.http://scripts.iucr.org/cgi-bin/paper?S2056989019015986crystal structure2h-1,2,6-thiadiazine 1,1-dioxidehepatitis bhbvhydrogen bondinghirshfeld surface analysismolecular docking study |
| spellingShingle | Alexandre V. Ivachtchenko Sergiy M. Kovalenko Dmitry V. Kravchenko Oleg D. Mitkin Vladimir V. Ivanov Thierry Langer 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 Acta Crystallographica Section E: Crystallographic Communications crystal structure 2h-1,2,6-thiadiazine 1,1-dioxide hepatitis b hbv hydrogen bonding hirshfeld surface analysis molecular docking study |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | crystal structure 2h-1,2,6-thiadiazine 1,1-dioxide hepatitis b hbv hydrogen bonding hirshfeld surface analysis molecular docking study |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019015986 |
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