Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives

doi:10.1007/s40242-018-8083-4

高等学校化学研究 ›› 2018, Vol. 34 ›› Issue (5): 744-750.doi: 10.1007/s40242-018-8083-4

Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives

HUA Xuewen¹, WEI Wei³, ZHU Liangliang², ZHOU Yunyun²

1. College of Agronomy, Liaocheng University, Liaocheng 252000, P. R. China;
2. State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, P. R. China;
3. Wuxi AppTec(Tianjin) Co., Ltd., Tianjin 300457, P. R. China

收稿日期:2018-03-14 修回日期:2018-06-11 出版日期:2018-10-01 发布日期:2018-06-26
通讯作者: ZHOU Yunyun,Email:zhouyunyun@fudan.edu.cn E-mail:zhouyunyun@fudan.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21502229), the Natural Science Foundation of Shandong Province, China(No.ZR2017BC053) and the Doctoral Research Startup Foundation of Liaocheng University, China (No.318051625).

Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives

HUA Xuewen¹, WEI Wei³, ZHU Liangliang², ZHOU Yunyun²

1. College of Agronomy, Liaocheng University, Liaocheng 252000, P. R. China;
2. State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, P. R. China;
3. Wuxi AppTec(Tianjin) Co., Ltd., Tianjin 300457, P. R. China

Received:2018-03-14 Revised:2018-06-11 Online:2018-10-01 Published:2018-06-26
Contact: ZHOU Yunyun,Email:zhouyunyun@fudan.edu.cn E-mail:zhouyunyun@fudan.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21502229), the Natural Science Foundation of Shandong Province, China(No.ZR2017BC053) and the Doctoral Research Startup Foundation of Liaocheng University, China (No.318051625).

摘要/Abstract

摘要： To further explore the structure-activity relationship(SAR) of amide bridge moeity of anthranilic diamides derivatives, a series of N-pyridylpyrazole derivatives was designed, synthesized and their biological activities were evaluated. The chemical structures of novel target compounds were confirmed by ¹H nuclear magnetic resonance (NMR), ¹³C NMR and elemental analyses(EA). Bioassay results of insecticidal activity demonstrated that the target compound 6h displayed 70% lethality rate against oriental armyworms at 200 mg/L. Moreover, most compounds displayed moderate to excellent antifungicidal activities against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 mg/L. In particular, compound 6e showed 61.5% and 92.3% inhibition rate against Cercospora arachidicola Hori and Botryosphaeria dothidea, which was superior to the commercial positive control Chlorothalonil. These results will provide a potential clue for exploring novel high-effective agrochemicals.

关键词: Anthranilic diamide, Biological activity, Antifungal agent

Abstract: To further explore the structure-activity relationship(SAR) of amide bridge moeity of anthranilic diamides derivatives, a series of N-pyridylpyrazole derivatives was designed, synthesized and their biological activities were evaluated. The chemical structures of novel target compounds were confirmed by ¹H nuclear magnetic resonance (NMR), ¹³C NMR and elemental analyses(EA). Bioassay results of insecticidal activity demonstrated that the target compound 6h displayed 70% lethality rate against oriental armyworms at 200 mg/L. Moreover, most compounds displayed moderate to excellent antifungicidal activities against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 mg/L. In particular, compound 6e showed 61.5% and 92.3% inhibition rate against Cercospora arachidicola Hori and Botryosphaeria dothidea, which was superior to the commercial positive control Chlorothalonil. These results will provide a potential clue for exploring novel high-effective agrochemicals.

Key words: Anthranilic diamide, Biological activity, Antifungal agent

HUA Xuewen, WEI Wei, ZHU Liangliang, ZHOU Yunyun. Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives[J]. 高等学校化学研究, 2018, 34(5): 744-750.

HUA Xuewen, WEI Wei, ZHU Liangliang, ZHOU Yunyun. Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives[J]. Chemical Research in Chinese Universities, 2018, 34(5): 744-750.

参考文献

[1] Marengo J. J., Hidalgo C., Bull R., Biophysical Journal, 1998, 74(3), 1263
[2] Isaacs A. K., Qi S., Sarpong R., Casida J. E., Chemical Research in Toxicology, 2012, 25(8), 1571
[3] Casida J. E., Chemical Research in Toxicology, 2015, 28(4), 560
[4] Gnamm C., Jeanguenat A., Dutton A. C., Grimm C., Kloer D. P., Crossthwaite A. J., Bioorganic & Medicinal Chemistry Letters, 2012, 22(11), 3800
[5] Lahm G. P., Stevenson T. M., Selby T. P., Freudenberger J. H., Cordova D., Flexner L., Bellin C. A., Dubas C. M., Smith B. K., Hughes K. A., Hollingshaus J. G., Clark C. E., Benner E. A., Bioorganic & Medicinal Chemistry Letters, 2007, 17(22), 6274
[6] Lahm G. P., Selby T. P., Freudenberger J. H., Stevenson T. M., Myers B. J., Seburyamo G., Smith B. K., Flexner L., Clark C. E., Cordova D., Bioorganic & Medicinal Chemistry Letters, 2005, 15(22), 4898
[7] Selby T. P., Lahm G. P., Stevenson T. M., Pest Management Science, 2017, 73(4), 658
[8] Selby T. P., Lahm G. P., Stevenson T. M., Hughes K. A., Cordova D., Annan I. B., Barry J. D., Benner E. A., Currie M. J., Pahutski T. F., Bioorganic & Medicinal Chemistry Letters, 2013, 23(23), 6341
[9] Lahm G. P., Cordova D., Barry J. D., Bioorganic & Medicinal Chemistry, 2009, 17(12), 4127
[10] Li Y., Mao M., Li Y., Xiong L., Li Z., Xu J., Physiological Entomology, 2011, 36(3), 230
[11] Forgash A. J., Pesticide Biochemistry and Physiology, 1984, 22(2), 178
[12] Roditakis E., Steinbach D., Moritz G., Vasakis E., Stavrakaki M., Ilias A., Garcia-Vidal L., Martinez-Aguirre M. D. R., Bielza P., Morou E., Silva J. E., Silva W. M., Siqueira Η. A. A., Iqbal S., Troczka B. J., Williamson M. S., Bass C., Tsagkarakou A., Vontas J., Nauen R., Insect Biochemistry and Molecular Biology, 2017, 80, 11
[13] Wu J., Song B. A., Hu D. Y., Yue M., Yang S., Pest Management Science, 2012, 68(5), 801
[14] Chen Y. B., Li J. L., Shao X. S., Xu X. Y., Li Z., Chinese Chemical Letters, 2013, 24(8), 673
[15] Mao M., Li Y., Liu Q., Zhou Y., Zhang X., Xiong L., Li Y., Li Z., Bioorganic & Medicinal Chemistry Letters, 2013, 23(1), 42
[16] Zhou Y., Feng Q., Di F., Liu Q., Wang D., Chen Y., Xiong L., Song H., Li Y., Li Z., Bioorganic & Medicinal Chemistry, 2013, 21(17), 4968
[17] Hua X., Mao W., Fan Z., Ji X., Li F., Zong G., Song H., Li J., Zhou L., Zhou L., Liang X., Wang G., Chen X., Australian Journal of Chemistry, 2014, 67(10), 1491
[18] Mao M. Z., Li Y. X., Zhou Y. Y., Zhang X. L., Liu Q. X., Di F. J., Song H. B., Xiong L. X., Li Y. Q., Li Z. M., Journal of Agricultural and Food Chemistry, 2014, 62(7), 1536
[19] Liu Q., Zhu R., Gao S., Ma S. H., Tang H. J., Yang J. J., Diao Y. M., Wang H. L., Zhu H. J., Pest Management Science, 2017, 73(5), 917
[20] Zhao Y., Li Y., Xiong L., Wang H., Li Z., Chinese Journal of Chemistry, 2012, 30(8), 1748
[21] Kon'Kov K., Bormasheva M., Russian Journal of Organic Chemistry, 2014, 50(11), 1636
[22] Zhang X., Li Y., Ma J., Zhu H., Wang B., Mao M., Xiong L., Li Y., Li Z., Bioorganic & Medicinal Chemistry, 2014, 22(1), 186
[23] Liu J. B., Li Y. X., Zhang X. L., Hua X. W., Wu C. C., Wei W., Wan Y. Y., Cheng D. D., Xiong L. X., Yang N., Song H. B., Li Z. M., Journal of Agricultural and Food Chemistry, 2016, 64(18), 3697
[24] Wang X. J., Tan J., Grozinger K., Betageri R., Kirrane T., Proudfoot J. R., Tetrahedron Letters, 2000, 41(28), 5321
[25] Kang S., Song B., Wu J., He M., Hu D., Jin L., Zeng S., Xue W., Yang S., European Journal of Medicinal Chemistry, 2013, 67, 14
[26] Wang B. L., Zhu H. W., Ma Y., Xiong L. X., Li Y. Q., Zhao Y., Zhang J. F., Chen Y. W., Zhou S., Li Z. M., Journal of Agricultural and Food Chemistry, 2013, 61(23), 5483
[27] Zhang J. F., Xu J. Y., Wang B. L., Li Y. X., Xiong L. X., Li Y. Q., Ma Y., Li Z. M., Journal of Agricultural and Food Chemistry, 2012, 60(31), 7565
[28] Liu C., Zhang J., Zhou Y., Wang B., Xiong L., Li Z., Chem. Res. Chinese Universities, 2014, 30(2), 228
[29] Abbott W. S., Journal of Economic Entomology, 1925, 18(2), 265
[30] Hua X., Mao W., Fan Z., Ji X., Li F., Zong G., Song H., Tatiana K., Morzherin Y. Y., Belskaya N. P., Bakulev V. A., Journal of Heterocyclic Chemistry, 2016, 53(3), 865

Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives

Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	LI Huangong, ZHAO Yangyang, SUN Pengwei, GAO Li, XIONG Lixia, YANG Na, ZHOU Sha, LI Yuxin, LI Zhengming. Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole[J]. 高等学校化学研究, 2021, 37(3): 655-661.
[2]	LIU Fei, LI Ren, YE Jing, REN Yujie, TANG Zhipeng, LI Rongchen, ZHANG Cuihua, LI Qunlin. Study of Aldo-keto Reductase 1C3 Inhibitor with Novel Framework for Treating Leukaemia Based on Virtual Screening and In vitro Biological Activity Testing[J]. 高等学校化学研究, 2021, 37(3): 778-786.
[3]	ZHAO Yangyang, LI Huangong, SUN Pengwei, GAO Li, ZHOU Sha, XIONG Lixia, YANG Na, LI Yuxin, LI Zhengming. Design, Synthesis, Biological Evaluation and SARs of Anthranilic Diamide Derivatives Containing Pyrrole Moieties[J]. 高等学校化学研究, 2020, 36(6): 1168-1173.
[4]	ZHANG Xiulan, ZHANG Huan, LIU Jingbo, XIONG Lixia, LI Zhengming. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole[J]. 高等学校化学研究, 2020, 36(5): 829-834.
[5]	CHENG Dandan, WEI Wei, LI Yuxin, HUA Xuewen, ZHOU Yunyun, LIU Jingbo, LI Yonghong, YU Shujing, XIONG Lixia, LI Zhengming. Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole Derivatives[J]. 高等学校化学研究, 2017, 33(5): 758-764.
[6]	LIU Jingbo, LI Yuxin, CHEN Youwei, WU Changchun, WAN Yingying, WEI Wei, XIONG Lixia, ZHANG Xiao, YU Shujing, LI Zhengming. Design, Synthesis and Biological Activities of Novel Anthranilic Diamides Containing Dihydroisoxazoline and Isoxazole[J]. 高等学校化学研究, 2016, 32(1): 41-48.
[7]	SHI Fangyuan, FANG Hao, XU Wenfang. Design, Synthesis and Biological Activity of Novel Chalcone Derivatives as Anti-influenza Agents[J]. 高等学校化学研究, 2016, 32(1): 28-34.
[8]	TANG Xiaobin, LI Zhenghui, LI Yonghong, LIU Wei, YU Peng, LI Lixin, GUO Yu, YANG Cheng. Synthesis and Biological Evaluation of Novel Saccharin Derivatives Containing 1,2,3-Triazole Moiety[J]. 高等学校化学研究, 2015, 31(1): 71-77.
[9]	LIU Chen, ZHANG Jifeng, ZHOU Yunyun, WANG Baolei, XIONG Lixia, LI Zhengming. Design, Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Oxime Ester and Diacylhydrazine Moieties[J]. 高等学校化学研究, 2014, 30(2): 228-234.
[10]	SUN Xiao-xiao, SUN Tao, WANG Tai-yi, ZHANG Yan, LIU Hui-juan, WANG Quan, NIU Guo-jun, LIU Wei, ZHOU Hong-gang, YANG Cheng. Synthesis and Characterization of Pyrazoleanthrone Derivatives as Aurora A Kinase Inhibitors[J]. 高等学校化学研究, 2013, 29(6): 1098-1103.
[11]	ZHANG Ji-feng, LIU Chen, LIU Peng-fei, YAN Tao, WANG Bao-lei, XIONG Li-xia, LI Zheng-ming. Synthesis and Biological Activities of Novel Anthranilic Diamides Analogues Containing Benzo[b]thiophene[J]. 高等学校化学研究, 2013, 29(4): 714-720.
[12]	SUN Jing-bo, LIU Rong-wang, XUAN Li-li, LENG Wei-chun, WU Jin-chang. Synthesis and Anti-HIV Activity of Triazolo-fused 3',4'-Cyclic and 4'-Spiro Nucleoside Analogues[J]. 高等学校化学研究, 2013, 29(3): 473-476.
[13]	KANG Yan-fang, WANG Dun-jia, XU Ben-po, WEI Xian-hong, ZHENG Jing. Synthesis, Characterization and Biological Activities of N-Acyl-3-(3-pyridyl)-5-aryl-pyrazoles[J]. 高等学校化学研究, 2013, 29(2): 227-230.
[14]	LIANG Di, YANG Xiao-hong, SUN Wei, WANG Wen-na, YANG Jin-zhu, LIU Yin-yan, WANG Guang-shu. Synthesis, Crystal Structure and Biological Activities of Naproxen-eugenol Ester Prodrug[J]. 高等学校化学研究, 2013, 29(2): 245-248.
[15]	ZHAO Yu, LI Yong-qiang, XIONG Li-xia, XU Li-ping, PENG Li-na, LI Fang, LI Zheng-ming. Design, Syntheses and Biological Activities of Novel Anthranilic Diamide Insecticides Containing N-Pyridylpyrazole[J]. 高等学校化学研究, 2013, 29(1): 51-56.