<i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity
Three new 4-phenylpicolin derivatives with a thiosemicarbazone structure were synthesized and evaluated for tuberculostatic activity. The compounds were obtained by the condensation of methyl 4-phenylpicolonimidate with the corresponding cycloalkylamino-1-carbothiohydrazides. The <sup>1</su...
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2022-08-01
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| author | Katarzyna Gobis Małgorzata Szczesio Andrzej Olczak Ida Mazerant-Politowicz Dagmara Ziembicka Barbara Pacholczyk-Sienicka Ewa Augustynowicz-Kopeć Agnieszka Głogowska Izabela Korona-Głowniak Andrzej Fruziński |
| author_facet | Katarzyna Gobis Małgorzata Szczesio Andrzej Olczak Ida Mazerant-Politowicz Dagmara Ziembicka Barbara Pacholczyk-Sienicka Ewa Augustynowicz-Kopeć Agnieszka Głogowska Izabela Korona-Głowniak Andrzej Fruziński |
| author_sort | Katarzyna Gobis |
| collection | DOAJ |
| description | Three new 4-phenylpicolin derivatives with a thiosemicarbazone structure were synthesized and evaluated for tuberculostatic activity. The compounds were obtained by the condensation of methyl 4-phenylpicolonimidate with the corresponding cycloalkylamino-1-carbothiohydrazides. The <sup>1</sup>H NMR temperature spectra obtained showed proton lability at the nitrogen atom N2, and X-ray crystallography confirmed the zwitterionic structure of all products. ADME calculations indicate that the compounds can be tested as future drugs. All compounds were absorbed in the gastrointestinal tract. All compounds also showed very good tuberculostatic activity (MIC 3.1–12.5 µg/mL). Derivative <b>1b</b> showed the best selectivity for <i>M. tuberculosis</i> compared to the other pathogenic species tested. The study has allowed the emergence of imine derivative <b>1b</b> as a good structure for further optimization in the search for antitubercular drugs. |
| first_indexed | 2024-03-09T04:10:33Z |
| format | Article |
| id | doaj.art-48f8db7256e84d009b17bade8efff216 |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-09T04:10:33Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-48f8db7256e84d009b17bade8efff2162023-12-03T14:00:57ZengMDPI AGMaterials1996-19442022-08-011516551310.3390/ma15165513<i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial ActivityKatarzyna Gobis0Małgorzata Szczesio1Andrzej Olczak2Ida Mazerant-Politowicz3Dagmara Ziembicka4Barbara Pacholczyk-Sienicka5Ewa Augustynowicz-Kopeć6Agnieszka Głogowska7Izabela Korona-Głowniak8Andrzej Fruziński9Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, 107 Gen. Hallera Ave., 80-416 Gdańsk, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, PolandDepartment of Organic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, 107 Gen. Hallera Ave., 80-416 Gdańsk, PolandInstitute of Organic Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, PolandDepartment of Microbiology, Institute of Tuberculosis and Pulmonary Diseases, 26 Płocka Str., 01-138 Warsaw, PolandDepartment of Microbiology, Institute of Tuberculosis and Pulmonary Diseases, 26 Płocka Str., 01-138 Warsaw, PolandDepartment of Pharmaceutical Microbiology, Faculty of Pharmacy, Medical University of Lublin, 1 Chodźki Street, 20-093 Lublin, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, PolandThree new 4-phenylpicolin derivatives with a thiosemicarbazone structure were synthesized and evaluated for tuberculostatic activity. The compounds were obtained by the condensation of methyl 4-phenylpicolonimidate with the corresponding cycloalkylamino-1-carbothiohydrazides. The <sup>1</sup>H NMR temperature spectra obtained showed proton lability at the nitrogen atom N2, and X-ray crystallography confirmed the zwitterionic structure of all products. ADME calculations indicate that the compounds can be tested as future drugs. All compounds were absorbed in the gastrointestinal tract. All compounds also showed very good tuberculostatic activity (MIC 3.1–12.5 µg/mL). Derivative <b>1b</b> showed the best selectivity for <i>M. tuberculosis</i> compared to the other pathogenic species tested. The study has allowed the emergence of imine derivative <b>1b</b> as a good structure for further optimization in the search for antitubercular drugs.https://www.mdpi.com/1996-1944/15/16/5513picolinohydrazonamidethiosemicarbazonessynthesistemperature NMRX-rayADME |
| spellingShingle | Katarzyna Gobis Małgorzata Szczesio Andrzej Olczak Ida Mazerant-Politowicz Dagmara Ziembicka Barbara Pacholczyk-Sienicka Ewa Augustynowicz-Kopeć Agnieszka Głogowska Izabela Korona-Głowniak Andrzej Fruziński <i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity Materials picolinohydrazonamide thiosemicarbazones synthesis temperature NMR X-ray ADME |
| title | <i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity |
| title_full | <i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity |
| title_fullStr | <i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity |
| title_full_unstemmed | <i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity |
| title_short | <i>N</i>′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity |
| title_sort | i n i substituted 4 phenylpicolinohydrazonamides with thiosemicarbazone moiety as new potential antitubercular agents synthesis structure and evaluation of antimicrobial activity |
| topic | picolinohydrazonamide thiosemicarbazones synthesis temperature NMR X-ray ADME |
| url | https://www.mdpi.com/1996-1944/15/16/5513 |
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