Synthesis and Biological Activity of 1-{4-[(2-Cyanoimino-1,3-thiazolidine-3-yl)methyl]thiazol-2-yl}-3-aroyl Ureas

doi:10.6023/cjoc201301068

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1568-1572.DOI: 10.6023/cjoc201301068 Previous Articles Next Articles

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1-{4-[(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-噻唑-2-基}-3-取代苯甲酰基脲类化合物的合成及其生物活性

戴红^a, 赵元飞^a, 牛平^a, 钱翊钧^a, 李永强^b, 方建新^b, 石玉军^a

a 南通大学化学化工学院南通 226019;
b 南开大学元素有机化学研究所天津 300071

收稿日期:2013-01-29 修回日期:2013-02-07 发布日期:2013-03-06
通讯作者: 李永强, 石玉军 E-mail:lyq@nankai.edu.cn;gaofz2005@yahoo.com.cn
基金资助:
国家自然科学基金(Nos. 21102077, 21202089);国家级大学生创新训练计划项目(No. 201210304039)和江苏省“六大人才高峰”(No. 2011-SWYY-009)资助项目.

Synthesis and Biological Activity of 1-{4-[(2-Cyanoimino-1,3-thiazolidine-3-yl)methyl]thiazol-2-yl}-3-aroyl Ureas

Dai Hong^a, Zhao Yuanfei^a, Niu Ping^a, Qian Yijun^a, Li Yongqiang^b, Fang Jianxin^b, Shi Yujun^a

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received:2013-01-29 Revised:2013-02-07 Published:2013-03-06
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21102077, 21202089), the Science and Technology Innovation Foundation for the College Students of China (No. 201210304039) and the Research Foundation of the Six People Peak of Jiangsu Province (No. 2011-SWYY-009).

In search of novel thiazole derivatives with potent biological activities, a series of new thiazole compounds 6 containing acyl urea moiety were synthesized by the condensation of 2-cyanoimino-3-(2-aminothiazol-4-ylmethyl)thiazolidine with various arylacylisocyanates. The structures of the target compounds were determined by ¹H NMR, MS and elemental analysis. The structures of 6a, 6e and 6h were further characterized by ¹³C NMR spectra. The bioassay data indicated that some of the title compounds showed fungicidal activities to some extent at the concentration of 50 μg/mL. For example, compound 6d displayed 65.3% inhibition rate against Gibberella zeae, compound 6f exhibited 67.3% inhibition rate against Cercospora arachidicola, and compound 6g showed 56.1% inhibition rate against Physalospora piricola.

Key words: acyl urea, thiazole, synthesis, biological activity

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Dai Hong, Zhao Yuanfei, Niu Ping, Qian Yijun, Li Yongqiang, Fang Jianxin, Shi Yujun. Synthesis and Biological Activity of 1-{4-[(2-Cyanoimino-1,3-thiazolidine-3-yl)methyl]thiazol-2-yl}-3-aroyl Ureas[J]. Chin. J. Org. Chem., 2013, 33(07): 1568-1572.

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1-{4-[(2-氰基亚胺基-1,3-噻唑烷-3-基)甲基]-噻唑-2-基}-3-取代苯甲酰基脲类化合物的合成及其生物活性

Synthesis and Biological Activity of 1-{4-[(2-Cyanoimino-1,3-thiazolidine-3-yl)methyl]thiazol-2-yl}-3-aroyl Ureas

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