Emine Kutlu , Fatih Mehmet Emen , Kübra Yıldırım , Cemilenur Ataş , Ruken Esra Demirdogen , Tuncay Yesilkaynak , Neslihan Kaya Kinaytürk , Ece Şimşek , Ahmet Yılmaz Çoban
{"title":"新型抗结核分枝杆菌硫脲衍生物:合成、表征及分子对接研究","authors":"Emine Kutlu , Fatih Mehmet Emen , Kübra Yıldırım , Cemilenur Ataş , Ruken Esra Demirdogen , Tuncay Yesilkaynak , Neslihan Kaya Kinaytürk , Ece Şimşek , Ahmet Yılmaz Çoban","doi":"10.1080/10426507.2023.2201503","DOIUrl":null,"url":null,"abstract":"<div><p> <em>N</em>-((2-chloropyridin-3-yl)carbamothioyl)thiophene-2-carboxamide (HL<sup>1</sup>), <em>N</em>-((6-methylpyridin-2-yl)carbamothioyl)thiophene-2-carboxamide (HL<sup>2</sup>), <em>N</em>-(allylcarbamothioyl)thiophene-2-carboxamide (HL<sup>3</sup>), 2-chloro-<em>N</em>-(methyl(1-phenylethyl)carbamothioyl)benzamide (HL<sup>4</sup>) and 2-chloro-<em>N</em>-(<em>bis</em>((R)-1-phenylethyl)carbamothioyl)benzamide (HL<sup>5</sup>) were synthesized and characterized via FT-IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and HR-MS techniques and HL<sup>3</sup> was characterized via a single crystal X-ray diffraction experiment. The antituberculosis activity of the synthesized thiourea derivatives was tested against the H37RV (ATCC27294), ATCC35822 (INH resistant), ATCC35838 (RIF resistant), ATCC35820 (STM resistant) and ATCC35837 (EMB resistant) standard bacteria strains. The thiourea derivatives were tested on two MDR and one primary drug-sensitive isolates with the microplate nitrate reductase test method. The results indicated that HL<sup>2</sup> and HL<sup>3</sup> had tuberculosis activity on some of the isolates. It was observed that HL<sup>4</sup> was the most effective among all the thiourea derivatives. The interaction mechanism of the synthesized compounds on 2X23, a tuberculosis protein, was investigated via molecular docking method. The interaction was observed to occur over S and Cl atoms in all the compounds. The compounds containing the methyl group were observed to interact via this group.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Novel thiourea derivatives against Mycobacterium tuberculosis: synthesis, characterization and molecular docking studies\",\"authors\":\"Emine Kutlu , Fatih Mehmet Emen , Kübra Yıldırım , Cemilenur Ataş , Ruken Esra Demirdogen , Tuncay Yesilkaynak , Neslihan Kaya Kinaytürk , Ece Şimşek , Ahmet Yılmaz Çoban\",\"doi\":\"10.1080/10426507.2023.2201503\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p> <em>N</em>-((2-chloropyridin-3-yl)carbamothioyl)thiophene-2-carboxamide (HL<sup>1</sup>), <em>N</em>-((6-methylpyridin-2-yl)carbamothioyl)thiophene-2-carboxamide (HL<sup>2</sup>), <em>N</em>-(allylcarbamothioyl)thiophene-2-carboxamide (HL<sup>3</sup>), 2-chloro-<em>N</em>-(methyl(1-phenylethyl)carbamothioyl)benzamide (HL<sup>4</sup>) and 2-chloro-<em>N</em>-(<em>bis</em>((R)-1-phenylethyl)carbamothioyl)benzamide (HL<sup>5</sup>) were synthesized and characterized via FT-IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and HR-MS techniques and HL<sup>3</sup> was characterized via a single crystal X-ray diffraction experiment. The antituberculosis activity of the synthesized thiourea derivatives was tested against the H37RV (ATCC27294), ATCC35822 (INH resistant), ATCC35838 (RIF resistant), ATCC35820 (STM resistant) and ATCC35837 (EMB resistant) standard bacteria strains. The thiourea derivatives were tested on two MDR and one primary drug-sensitive isolates with the microplate nitrate reductase test method. The results indicated that HL<sup>2</sup> and HL<sup>3</sup> had tuberculosis activity on some of the isolates. It was observed that HL<sup>4</sup> was the most effective among all the thiourea derivatives. The interaction mechanism of the synthesized compounds on 2X23, a tuberculosis protein, was investigated via molecular docking method. The interaction was observed to occur over S and Cl atoms in all the compounds. The compounds containing the methyl group were observed to interact via this group.</p></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650723000527\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650723000527","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Novel thiourea derivatives against Mycobacterium tuberculosis: synthesis, characterization and molecular docking studies
N-((2-chloropyridin-3-yl)carbamothioyl)thiophene-2-carboxamide (HL1), N-((6-methylpyridin-2-yl)carbamothioyl)thiophene-2-carboxamide (HL2), N-(allylcarbamothioyl)thiophene-2-carboxamide (HL3), 2-chloro-N-(methyl(1-phenylethyl)carbamothioyl)benzamide (HL4) and 2-chloro-N-(bis((R)-1-phenylethyl)carbamothioyl)benzamide (HL5) were synthesized and characterized via FT-IR, 1H-NMR, 13C-NMR and HR-MS techniques and HL3 was characterized via a single crystal X-ray diffraction experiment. The antituberculosis activity of the synthesized thiourea derivatives was tested against the H37RV (ATCC27294), ATCC35822 (INH resistant), ATCC35838 (RIF resistant), ATCC35820 (STM resistant) and ATCC35837 (EMB resistant) standard bacteria strains. The thiourea derivatives were tested on two MDR and one primary drug-sensitive isolates with the microplate nitrate reductase test method. The results indicated that HL2 and HL3 had tuberculosis activity on some of the isolates. It was observed that HL4 was the most effective among all the thiourea derivatives. The interaction mechanism of the synthesized compounds on 2X23, a tuberculosis protein, was investigated via molecular docking method. The interaction was observed to occur over S and Cl atoms in all the compounds. The compounds containing the methyl group were observed to interact via this group.
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Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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