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Synthesis and Evaluation of 1,3,4‐Thiadiazole Derivatives Containing Cyclopentylpropionamide as Potential Antibacterial Agent
Author(s) -
Zhang Min,
Xu Weiming,
Wei Kun,
Liu Hongwu,
Yang Qin,
Liu Qin,
Yang Liyun,
Luo Yuqin,
Xue Wei
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3576
Subject(s) - chemistry , antibacterial activity , bioassay , positive control , proton nmr , copper , carbon 13 nmr , stereochemistry , minimum inhibitory concentration , nuclear chemistry , combinatorial chemistry , bacteria , in vitro , organic chemistry , traditional medicine , biochemistry , medicine , genetics , biology
This study aimed to identify new strategies for the control of these plant bacterial diseases by combining a pharmacophoric group of different bioactive compounds. A series of 3‐cyclopentylpropionamide containing 1,3,4‐thiadiazole derivatives was synthesized and characterized via 1 H‐NMR, 13 C‐NMR, and HRMS. Bioassay results indicated that compounds 7a , 7d , 7j , 7m , 7n , and 7s had excellent antibacterial activity compared with the positive control. Among them, compound 7a exhibited remarkable inhibitory effect against Xoo with an EC 50 of 21.41 μg/mL, which surpassed that of thiodiazole copper (67.71 μg/mL) and bismerthiazol (69.05 μg/mL). Greenhouse condition tests further revealed that 7a had approximately equal curative activity and better protection activity (41.58%) against bacterial leaf blight of rice than that of thiodiazole copper and bismerthiazol (46.86 and 42.25%, respectively). Structure–activity relationship analysis exhibited that sulfone fragment favored inhibition. Overall, this study suggested that derivatives containing 1,3,4‐thiadiazole 3‐cyclopentylpropanamide can be used as new lead compounds for bactericide studies.