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Design, synthesis, and bioassay of novel 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole derivatives containing a 1,3,4-thiadiazole thioether or sulfone moiety
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-12-27 , DOI: 10.1002/jhet.4436 Huanlin Zheng 1 , Jiqing Kuang 1 , Hong Zhang 1 , Xue Niu 1 , Zhibing Wu 1
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-12-27 , DOI: 10.1002/jhet.4436 Huanlin Zheng 1 , Jiqing Kuang 1 , Hong Zhang 1 , Xue Niu 1 , Zhibing Wu 1
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A series of novel 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole derivatives containing a 1,3,4-thiadiazole thioether or sulfone moiety were designed and synthesized. All the title compounds were confirmed by 1H NMR, 13C NMR, and MS, and the intermediate 2 and title compound 5e were confirmed by single crystal X-ray diffraction analysis. Bioassay evaluation revealed that compound 5a (54.2 ± 2.0%) and 5r (75.2 ± 3.9%) exhibited good curative and protection activity against TMV, respectively, which was slightly lower than that of ningnanmycin (57.1 ± 2.2% and 73.8 ± 3.4%). Compound 5b (64.7 ± 8.5% and 67.7 ± 2.1%) exhibited good curative and protective activity against CMV, which was better than that of ningnanmycin (55.8 ± 1.4% and 64.2 ± 5.8%). The lethality rates of 5a, 5c, 5d, 5h, 5j, 5n, 5o, 5p, 5q, 5r, 5t, 6a, and 6e against C. pipiens were 100% at a concentration of 10 μg/ml, as well as chlorantraniliprole (100%). These results may provide enough support to justify further molecular design and derivation.
中文翻译：
含有 1,3,4-噻二唑硫醚或砜部分的新型 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole 衍生物的设计、合成和生物测定
设计并合成了一系列含有 1,3,4-噻二唑硫醚或砜部分的新型 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole 衍生物。所有标题化合物均经1 H NMR、13 C NMR和MS确认，中间体2和标题化合物5e经单晶X射线衍射分析确认。生物测定评价显示，化合物5a（54.2±2.0%）和5r（75.2±3.9%）分别对TMV表现出良好的治疗和保护活性，略低于宁南霉素（57.1±2.2%和73.8±3.4%） . 化合物5b（64.7±8.5%和67.7±2.1%）对CMV表现出良好的治疗和保护活性，优于宁南霉素（55.8±1.4%和64.2±5.8%）。5a , 5c , 5d , 5h , 5j , 5n , 5o , 5p , 5q , 5r , 5t , 6a , 6e对C. pipiens的致死率为100%，浓度为10 μg/ml，氯虫苯甲酰胺(100%)。这些结果可能为进一步的分子设计和推导提供足够的支持。
更新日期：2021-12-27
中文翻译：
含有 1,3,4-噻二唑硫醚或砜部分的新型 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole 衍生物的设计、合成和生物测定
设计并合成了一系列含有 1,3,4-噻二唑硫醚或砜部分的新型 1-(3-chloropyridin-2-yl)-5-amino-4-pyrazole 衍生物。所有标题化合物均经1 H NMR、13 C NMR和MS确认，中间体2和标题化合物5e经单晶X射线衍射分析确认。生物测定评价显示，化合物5a（54.2±2.0%）和5r（75.2±3.9%）分别对TMV表现出良好的治疗和保护活性，略低于宁南霉素（57.1±2.2%和73.8±3.4%） . 化合物5b（64.7±8.5%和67.7±2.1%）对CMV表现出良好的治疗和保护活性，优于宁南霉素（55.8±1.4%和64.2±5.8%）。5a , 5c , 5d , 5h , 5j , 5n , 5o , 5p , 5q , 5r , 5t , 6a , 6e对C. pipiens的致死率为100%，浓度为10 μg/ml，氯虫苯甲酰胺(100%)。这些结果可能为进一步的分子设计和推导提供足够的支持。
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