Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine
Tuberculosis remains one of the most common diseases affecting developing countries due to difficult living conditions, the rapidly increasing resistance of <i>M. tuberculosis</i> strains and the small number of effective anti-tuberculosis drugs. This study concerns the relationship betw...
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| Online Access: | https://www.mdpi.com/1996-1944/15/1/349 |
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| author | Katarzyna Gobis Małgorzata Szczesio Andrzej Olczak Tomasz Pawlak Ewa Augustynowicz-Kopeć Malwina Krause Marek L. Główka |
| author_facet | Katarzyna Gobis Małgorzata Szczesio Andrzej Olczak Tomasz Pawlak Ewa Augustynowicz-Kopeć Malwina Krause Marek L. Główka |
| author_sort | Katarzyna Gobis |
| collection | DOAJ |
| description | Tuberculosis remains one of the most common diseases affecting developing countries due to difficult living conditions, the rapidly increasing resistance of <i>M. tuberculosis</i> strains and the small number of effective anti-tuberculosis drugs. This study concerns the relationship between molecular structure observed in a solid-state by X-ray diffraction and the <sup>15</sup>N NMR of a group of pyridine derivatives, from which promising activity against <i>M. tuberculosis</i> was reported earlier. It was found that the compounds exist in two tautomeric forms: neutral and zwitterionic. The latter form forced the molecules to adopt a stable, unique, flat frame due to conjugation and the intramolecular hydrogen bond system. As the compounds exist in a zwitterionic form in the crystal state generally showing higher activity against tuberculosis, it may indicate that this geometry of molecules is the “active” form. |
| first_indexed | 2024-03-10T03:32:30Z |
| format | Article |
| id | doaj.art-1da42635c33442dfb505ea76cef5ccb5 |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T03:32:30Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-1da42635c33442dfb505ea76cef5ccb52023-11-23T11:51:56ZengMDPI AGMaterials1996-19442022-01-0115134910.3390/ma15010349Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of PyridineKatarzyna Gobis0Małgorzata Szczesio1Andrzej Olczak2Tomasz Pawlak3Ewa Augustynowicz-Kopeć4Malwina Krause5Marek L. Główka6Department of Organic Chemistry, Medical University of Gdańsk, 107 Gen. Hallera Av., 80-438 Gdansk, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandCentre of Molecular and Macromolecular Studies, Polish Academy of Science, 112 Sienkiewicza, 90-363 Lodz, PolandDepartment of Microbiology, National Tuberculosis and Lung Diseases Research Institute, 26 Płocka Str., 01-138 Warsaw, PolandDepartment of Organic Chemistry, Medical University of Gdańsk, 107 Gen. Hallera Av., 80-438 Gdansk, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandTuberculosis remains one of the most common diseases affecting developing countries due to difficult living conditions, the rapidly increasing resistance of <i>M. tuberculosis</i> strains and the small number of effective anti-tuberculosis drugs. This study concerns the relationship between molecular structure observed in a solid-state by X-ray diffraction and the <sup>15</sup>N NMR of a group of pyridine derivatives, from which promising activity against <i>M. tuberculosis</i> was reported earlier. It was found that the compounds exist in two tautomeric forms: neutral and zwitterionic. The latter form forced the molecules to adopt a stable, unique, flat frame due to conjugation and the intramolecular hydrogen bond system. As the compounds exist in a zwitterionic form in the crystal state generally showing higher activity against tuberculosis, it may indicate that this geometry of molecules is the “active” form.https://www.mdpi.com/1996-1944/15/1/349tuberculostatic activitySAR-analysis2-amidinothiosemicarbazonespyridinecrystal state X-ray<sup>15</sup>N NMR study |
| spellingShingle | Katarzyna Gobis Małgorzata Szczesio Andrzej Olczak Tomasz Pawlak Ewa Augustynowicz-Kopeć Malwina Krause Marek L. Główka Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine Materials tuberculostatic activity SAR-analysis 2-amidinothiosemicarbazones pyridine crystal state X-ray <sup>15</sup>N NMR study |
| title | Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine |
| title_full | Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine |
| title_fullStr | Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine |
| title_full_unstemmed | Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine |
| title_short | Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine |
| title_sort | relationship between the crystal structure and tuberculostatic activity of some 2 amidinothiosemicarbazone derivatives of pyridine |
| topic | tuberculostatic activity SAR-analysis 2-amidinothiosemicarbazones pyridine crystal state X-ray <sup>15</sup>N NMR study |
| url | https://www.mdpi.com/1996-1944/15/1/349 |
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