Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives

doi:10.6023/cjoc201606038

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 218-225.DOI: 10.6023/cjoc201606038 Previous Articles Next Articles

NOTE

新型蒎烷基吡唑酰胺类衍生物的合成及其生物活性研究

芮坚^a, 张齐^a, 王欣^b, 徐徐^a,c,d, 徐海军^a, 饶卫东^a, 王石发^a,c,d

a 南京林业大学化学工程学院南京 210037;
b 南京农业大学植物保护学院南京 210095;
c 江苏省生物质绿色燃料与化学品重点实验室南京 210037;
d 广西林产化学与工程重点实验室南宁 530008

收稿日期:2016-06-24 修回日期:2016-08-04 发布日期:2016-09-01
通讯作者: 王石发 E-mail:wsfyyq@njfu.com.cn
基金资助:
江苏省高校自然科学研究重大项目（No. 14KJ220001）、国家自然科学基金（No. 31470529）和广西林产化学与工程重点实验室开放基金（No. JSBEM2014010）资助项目.

Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives

Rui Jian^a, Zhang Qi^a, Wang Xin^b, Xu Xu^a,c,d, Xu Haijun^a, Rao Weidong^a, Wang Shifa^a,c,d

a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b College of Plant Protection, Nanjing Agricultural University, Nanjing 210095;
c Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037;
d Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008

Received:2016-06-24 Revised:2016-08-04 Published:2016-09-01
Supported by:
Project supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China(No. 14KJ220001), the National Natural Science Foundation of China(No. 31470529), and the Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products(No. GXFC15-02).

Novel pinanyl pyrazole derivatives were synthesized from nopinone and their bioactivities were also examined in this paper.The intermediate compounds 3-arylidenenopinones 2a~2g were synthesized by condensation of aromatic aldehydes and nopinone,and pinanyl pyrazole derivatives 3a~3g were subsequently obtained by cyclization and dehydroaromatization of compounds 2a~2g and hydrazine hydrate in the circumstance of N,N-dimethylformamide(DMT).The target compound pinanyl pyrazole acetamide derivatives 4a~4g were synthesized by alkylation using 2-chloroacetamide as the alkylating agent under the condition of base catalysis.The structures of synthesized compounds were characterized by ¹H NMR,¹³C NMR,IR,HRMS,and X-ray diffraction analysis.Biological activities evaluation of compounds 3a~3g and 4a~4g were performed including antibacterial and insecticidal activities on Tinocallis kahawaluokalani.Test results showed that compound 4g was a more potent bactericide and fungicide than others because of its good activities against bacteria and fungi;furthermore,compound 4g had shown the better insecticidal activity against Tinocallis kahawaluokalani than the others.

Key words: nopinone, pinanyl pyrazole derivatives, bacteriostatic activity, insecticidal activity

Cite this article

Rui Jian, Zhang Qi, Wang Xin, Xu Xu, Xu Haijun, Rao Weidong, Wang Shifa. Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives[J]. Chin. J. Org. Chem., 2017, 37(1): 218-225.

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新型蒎烷基吡唑酰胺类衍生物的合成及其生物活性研究

Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives

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