Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety
<b>A</b>bstract:<b> </b>In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4-oxadiazole structure. Antibacterial activity against two...
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MDPI AG
2020-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/7/1488 |
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| author | Lei Wang Xia Zhou Hui Lu Xianfu Mu Linhong Jin |
| author_facet | Lei Wang Xia Zhou Hui Lu Xianfu Mu Linhong Jin |
| author_sort | Lei Wang |
| collection | DOAJ |
| description | <b>A</b>bstract:<b> </b>In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4-oxadiazole structure. Antibacterial activity against two phytopathogens, <i>Xanthomonas oryzae </i>pv.<i> oryzae (Xoo) </i>and<i> Xanthomonas axonopodis </i>pv.<i> citri</i> <i>(Xac)</i>, was assayed in vitro. The preliminary results indicated that ten compounds including <b>4a-1</b>-<b>4a-4</b> and <b>4a-11</b>-<b>4a-16</b> had good antibacterial activity against <i>Xoo</i>, with EC<sub>50</sub> values ranging from 50.1-112.5 <i>µ</i>M, which was better than those of Bismerthiazol (253.5 <i>µ</i>M) and Thiodiazole copper (467.4 <i>µ</i>M). Meanwhile, <b>4a-1</b>, <b>4a-2</b>, <b>4a-3 </b>and <b>4a-</b><b>4</b> demonstrated good inhibitory effect against <i>Xanthomonas</i> <i>axonopodis pv. citri</i> with EC<sub>50</sub> values around 95.8-155.2 <i>µ</i>M which were better than those of bismerthiazol (274.3 <i>µ</i>M) and thiodiazole copper (406.3 <i>µ</i>M). In addition, in vivo protection activity of compound <b>4a-2</b> and <b>4a-3</b> against rice bacterial leaf blight was 68.6% and 62.3%, respectively, which were better than bismerthiazol (49.6%) and thiodiazole copper (42.2%). Curative activity of compound <b>4a-2</b> and <b>4a-3</b> against rice bacterial leaf blight was 62.3% and 56.0%, which were better than bismerthiazol (42.9%) and thiodiazole copper (36.1%). Through scanning electron microscopy (SEM) analysis, it was observed that compound <b>4a-2</b> caused the cell membrane of <i>Xanthomonas oryzae</i> pv. <i>oryzae</i> ruptured or deformed. The present results indicated novel derivatives of 5-phenyl sulfonate methyl 1,3,4-oxadiazole might be potential antibacterial agents. |
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| last_indexed | 2024-12-13T15:44:56Z |
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| spelling | doaj.art-517c9f3de0a14427812b86cac76da4402022-12-21T23:39:43ZengMDPI AGMolecules1420-30492020-03-01257148810.3390/molecules25071488molecules25071488Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate MoietyLei Wang0Xia Zhou1Hui Lu2Xianfu Mu3Linhong Jin4State 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, 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, China<b>A</b>bstract:<b> </b>In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4-oxadiazole structure. Antibacterial activity against two phytopathogens, <i>Xanthomonas oryzae </i>pv.<i> oryzae (Xoo) </i>and<i> Xanthomonas axonopodis </i>pv.<i> citri</i> <i>(Xac)</i>, was assayed in vitro. The preliminary results indicated that ten compounds including <b>4a-1</b>-<b>4a-4</b> and <b>4a-11</b>-<b>4a-16</b> had good antibacterial activity against <i>Xoo</i>, with EC<sub>50</sub> values ranging from 50.1-112.5 <i>µ</i>M, which was better than those of Bismerthiazol (253.5 <i>µ</i>M) and Thiodiazole copper (467.4 <i>µ</i>M). Meanwhile, <b>4a-1</b>, <b>4a-2</b>, <b>4a-3 </b>and <b>4a-</b><b>4</b> demonstrated good inhibitory effect against <i>Xanthomonas</i> <i>axonopodis pv. citri</i> with EC<sub>50</sub> values around 95.8-155.2 <i>µ</i>M which were better than those of bismerthiazol (274.3 <i>µ</i>M) and thiodiazole copper (406.3 <i>µ</i>M). In addition, in vivo protection activity of compound <b>4a-2</b> and <b>4a-3</b> against rice bacterial leaf blight was 68.6% and 62.3%, respectively, which were better than bismerthiazol (49.6%) and thiodiazole copper (42.2%). Curative activity of compound <b>4a-2</b> and <b>4a-3</b> against rice bacterial leaf blight was 62.3% and 56.0%, which were better than bismerthiazol (42.9%) and thiodiazole copper (36.1%). Through scanning electron microscopy (SEM) analysis, it was observed that compound <b>4a-2</b> caused the cell membrane of <i>Xanthomonas oryzae</i> pv. <i>oryzae</i> ruptured or deformed. The present results indicated novel derivatives of 5-phenyl sulfonate methyl 1,3,4-oxadiazole might be potential antibacterial agents.https://www.mdpi.com/1420-3049/25/7/14881,3,4-oxadiazole derivativesantibacterial activity<i>xanthomonas oryzae</i> pv. <i>oryzae</i><i>xanthomonas axonopodis</i> pv. <i>citri</i>scanning electron microscopy |
| spellingShingle | Lei Wang Xia Zhou Hui Lu Xianfu Mu Linhong Jin Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety Molecules 1,3,4-oxadiazole derivatives antibacterial activity <i>xanthomonas oryzae</i> pv. <i>oryzae</i> <i>xanthomonas axonopodis</i> pv. <i>citri</i> scanning electron microscopy |
| title | Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety |
| title_full | Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety |
| title_fullStr | Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety |
| title_full_unstemmed | Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety |
| title_short | Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety |
| title_sort | synthesis and antibacterial evaluation of novel 1 3 4 oxadiazole derivatives containing sulfonate carboxylate moiety |
| topic | 1,3,4-oxadiazole derivatives antibacterial activity <i>xanthomonas oryzae</i> pv. <i>oryzae</i> <i>xanthomonas axonopodis</i> pv. <i>citri</i> scanning electron microscopy |
| url | https://www.mdpi.com/1420-3049/25/7/1488 |
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