Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties
A series of new <i>N</i>-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by <sup>1</sup>H-NMR, <sup>13</sup&g...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/8/1772 |
| _version_ | 1827718821628084224 |
|---|---|
| author | Hui Lu Xia Zhou Lei Wang Linhong Jin |
| author_facet | Hui Lu Xia Zhou Lei Wang Linhong Jin |
| author_sort | Hui Lu |
| collection | DOAJ |
| description | A series of new <i>N</i>-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and HRMS. Their in vitro antibacterial activities were evaluated against three kinds of bacteria—<i>Xanthomonas oryzae</i> pv. <i>Oryzae</i> (<i>Xoo</i>), <i>Xanthomonas axonopodis</i> pv. <i>Citri</i> (<i>Xac</i>) and <i>X.oryzae</i> pv<i>. oryzicola</i> (<i>Xoc</i>)—showing promising results. The minimum 50% effective concentration (EC<sub>50</sub>) value of <i>N-</i>(4-((4-(4-fluoro-phenyl)thiazol-2-yl)amino)phenyl)acetamide (<b>A</b><sub>1</sub>) is 156.7 µM, which is superior to bismerthiazol (230.5 µM) and thiodiazole copper (545.2 µM). A scanning electron microscopy (SEM) investigation has confirmed that compound <b>A<sub>1</sub></b> could cause cell membrane rupture of <i>Xoo</i>. In addition, the nematicidal activity of the compounds against <i>Meloidogyne incognita</i> (<i>M. incognita</i>) was also tested, and compound <b>A</b><sub>23</sub> displayed excellent nematicidal activity, with mortality of 100% and 53.2% at 500 μg/mL and 100 μg/mL after 24 h of treatment, respectively. The preliminary structure-activity relationship (SAR) studies of these compounds are also briefly described. These results demonstrated that phenylacetamide derivatives may be considered as potential leads in the design of antibacterial agents. |
| first_indexed | 2024-03-10T20:31:15Z |
| format | Article |
| id | doaj.art-b02d2570254b49449526cb841aa1e998 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T20:31:15Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b02d2570254b49449526cb841aa1e9982023-11-19T21:26:00ZengMDPI AGMolecules1420-30492020-04-01258177210.3390/molecules25081772Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole MoietiesHui Lu0Xia Zhou1Lei Wang2Linhong Jin3State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, ChinaState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, ChinaA series of new <i>N</i>-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and HRMS. Their in vitro antibacterial activities were evaluated against three kinds of bacteria—<i>Xanthomonas oryzae</i> pv. <i>Oryzae</i> (<i>Xoo</i>), <i>Xanthomonas axonopodis</i> pv. <i>Citri</i> (<i>Xac</i>) and <i>X.oryzae</i> pv<i>. oryzicola</i> (<i>Xoc</i>)—showing promising results. The minimum 50% effective concentration (EC<sub>50</sub>) value of <i>N-</i>(4-((4-(4-fluoro-phenyl)thiazol-2-yl)amino)phenyl)acetamide (<b>A</b><sub>1</sub>) is 156.7 µM, which is superior to bismerthiazol (230.5 µM) and thiodiazole copper (545.2 µM). A scanning electron microscopy (SEM) investigation has confirmed that compound <b>A<sub>1</sub></b> could cause cell membrane rupture of <i>Xoo</i>. In addition, the nematicidal activity of the compounds against <i>Meloidogyne incognita</i> (<i>M. incognita</i>) was also tested, and compound <b>A</b><sub>23</sub> displayed excellent nematicidal activity, with mortality of 100% and 53.2% at 500 μg/mL and 100 μg/mL after 24 h of treatment, respectively. The preliminary structure-activity relationship (SAR) studies of these compounds are also briefly described. These results demonstrated that phenylacetamide derivatives may be considered as potential leads in the design of antibacterial agents.https://www.mdpi.com/1420-3049/25/8/1772synthesisthiazolenematicidal activityantibacterial activitystructure-activity relationship |
| spellingShingle | Hui Lu Xia Zhou Lei Wang Linhong Jin Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties Molecules synthesis thiazole nematicidal activity antibacterial activity structure-activity relationship |
| title | Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties |
| title_full | Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties |
| title_fullStr | Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties |
| title_full_unstemmed | Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties |
| title_short | Synthesis and Antibacterial Evaluation of <i>N</i>-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties |
| title_sort | synthesis and antibacterial evaluation of i n i phenylacetamide derivatives containing 4 arylthiazole moieties |
| topic | synthesis thiazole nematicidal activity antibacterial activity structure-activity relationship |
| url | https://www.mdpi.com/1420-3049/25/8/1772 |
| work_keys_str_mv | AT huilu synthesisandantibacterialevaluationofiniphenylacetamidederivativescontaining4arylthiazolemoieties AT xiazhou synthesisandantibacterialevaluationofiniphenylacetamidederivativescontaining4arylthiazolemoieties AT leiwang synthesisandantibacterialevaluationofiniphenylacetamidederivativescontaining4arylthiazolemoieties AT linhongjin synthesisandantibacterialevaluationofiniphenylacetamidederivativescontaining4arylthiazolemoieties |