Iodine-mediated oxidative cyclization for one pot synthesis of new 8-hydroxyquinaldine derivatives containing a N-phenylpyrazole moiety as pesticidal agents

被引：14

作者：

Xu, Ting ^{[1
]}

Wang, Xiaoguang ^{[1
]}

Zhang, Qian ^{[1
]}

Fan, Jiangping ^{[1
]}

Liu, Liu ^{[1
]}

Liu, Mingzhu ^{[1
]}

Zhang, Haojie ^{[1
]}

Li, Jing ^{[1
]}

Guo, Yong ^{[1
]}

机构：

[1] Zhengzhou Univ, Minist Educ, Key Lab Adv Drug Preparat Technol, Sch Pharmaceut Sci, Zhengzhou 450001, Henan, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2018年 / 28卷 / 20期

基金：

中国国家自然科学基金;

关键词：

8-Hydroxyquinaldine; N-Phenylpyrazole; Structural modification; Pesticidal activities; Structure-activity relationship; PYRAZOLE OXIME DERIVATIVES; BIOLOGICAL EVALUATION; INSECTICIDAL ACTIVITY; SARISAN ANALOGS; DESIGN; ANTIBACTERIAL; BIOACTIVITIES; CHEMISTRY; PROGRESS;

D O I：

10.1016/j.bmcl.2018.08.041

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In continuation of our research aimed at discovery and development of new pesticidal agents, a series of new 8hydroxyquinaldine derivatives containing a N-phenylpyrazole moiety were prepared and their structures were characterized by H-1 NMR, IR, ESI-MS and mp. Meanwhile, an efficient way of using iodine-mediated oxidative cyclization for one pot synthesis of these 8-hydroxyquinaldine derivatives containing a N-phenylpyrazole moiety was developed. The bioassay showed that compounds 8g and 9f exhibited potent pesticidal activities against both Mythimna separata Walker and Plutella xylostella Linnaeus. The structure-activity relationships were also discussed.

引用

页码：3376 / 3380

页数：5

共 31 条

[1] A review on anticancer potential of bioactive heterocycle quinoline [J].

Afzal, Obaid ;

Kumar, Suresh ;

Haider, Md Rafi ;

Ali, Md Rahmat ;

Kumar, Rajiv ;

Jaggi, Manu ;

Bawa, Sandhya .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :871-910

[2] Design, Synthesis and Bioactivities of Novel Isoxazole-Containing Pyrazole Oxime Derivatives [J].

Dai, Hong ;

Yao, Wei ;

Fang, Yuan ;

Sun, Siyu ;

Shi, Yujun ;

Chen, Jia ;

Jiang, Guoqing ;

Shi, Jian .

MOLECULES, 2017, 22 (12)

[3] Development of novel bis-pyrazole derivatives as antitumor agents with potent apoptosis induction effects and DNA damage [J].

Dai, Hong ;

Ge, Shushan ;

Guo, Jing ;

Chen, Shi ;

Huang, Meiling ;

Yang, Jiaying ;

Sun, Siyu ;

Ling, Yong ;

Shi, Yujun .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :1066-1076

[4] Design, synthesis, and bioactivities of novel oxadiazole-substituted pyrazole oximes [J].

Dai, Hong ;

Chen, Jia ;

Li, Gang ;

Ge, Shushan ;

Shi, Yujun ;

Fang, Yuan ;

Ling, Yong .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (04) :950-953

[5] Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 1,2,3-thiadiazole moiety [J].

Dai, Hong ;

Ge, Shushan ;

Li, Gang ;

Chen, Jia ;

Shi, Yujun ;

Ye, Linyu ;

Ling, Yong .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (18) :4504-4507

[6] Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives [J].

Dai, Hong ;

Li, Gang ;

Chen, Jia ;

Shi, Yujun ;

Ge, Shushan ;

Fan, Chongguang ;

He, Haibing .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (15) :3818-3821

[7] Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety [J].

Dai, Hong ;

Chen, Jia ;

Li, Hong ;

Dai, Baojiang ;

He, Haibing ;

Fang, Yuan ;

Shi, Yujun .

MOLECULES, 2016, 21 (03)

[8] The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity [J].

Dai, Hong ;

Xiao, Yan-Shuang ;

Li, Zhong ;

Xu, Xiao-Yong ;

Qian, Xu-Hong .

CHINESE CHEMICAL LETTERS, 2014, 25 (07) :1014-1016

[9] Transcriptome analysis of molecular mechanisms responsible for light-stress response in Mythimna separata (Walker) [J].

Duan, Yun ;

Gong, ZhongJun ;

Wu, RenHai ;

Miao, Jin ;

Jiang, YueLi ;

Li, Tong ;

Wu, XiaoBo ;

Wu, YuQing .

SCIENTIFIC REPORTS, 2017, 7

[10] Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents [J].

El Shehry, Mohamed F. ;

Ghorab, Mostafa M. ;

Abbas, Samir Y. ;

Fayed, Eman A. ;

Shedid, Said A. ;

Ammar, Yousry A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :1463-1473

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