Synthesis and Biological Activity of Novel Anthranilic Diamides Containing N-Substituted Arylmethylene Moieties

doi:10.1007/s40242-013-3038-2

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (6): 1134-1139.doi: 10.1007/s40242-013-3038-2

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Synthesis and Biological Activity of Novel Anthranilic Diamides Containing N-Substituted Arylmethylene Moieties

ZHANG Xiu-lan¹, LIU Ai-lin², ZHAO Yu¹, XIONG Li-xia¹, LI Zheng-ming¹

1. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China;
2. Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China

Received:2013-01-21 Revised:2013-03-01 Online:2013-12-01 Published:2013-04-28
Contact: LI Zheng-ming E-mail:nkzml@vip.163.com
Supported by:
Supported by the National Basic Research Program of China(No.2010CB126106), the National Key Technologies R&D Program, China(No.2011BAE06B05) and the Specialized Research Fund for Doctorial Program of Higher Education, China (No.20110031110017).

Abstract

Abstract:

A series of novel anthranilic diamides containing N-substituted arylmethyl moieties was designed and synthesized, in which the bond distance and conjugation pattern between pyrazole and pyridine rings contained in Chlorantraniliprole were changed. Their structures were confirmed by ¹H NMR, IR, elemental analysis or high resolution mass spectromentry(HRMS), and the conformation of compound 4d was confirmed by X-ray diffraction. The preliminary bioassay results indicate that all the target compounds exhibited moderate insecticidal activity against oriental armyworm at 200 mg/L and some of them presented favorable antitumor activities against human lung cancer cells(A549), liver cancer cells(Bel7402) and colon cancer cells(HCT-8) in vitro by microculture tetrazolium(MTT) method, among which compound 6j afforded the best anti-proliferative activity at 5 μg/mL.

Key words: N-Substituted arylmethylene, Insecticidal activity, Antitumor activity

ZHANG Xiu-lan, LIU Ai-lin, ZHAO Yu, XIONG Li-xia, LI Zheng-ming. Synthesis and Biological Activity of Novel Anthranilic Diamides Containing N-Substituted Arylmethylene Moieties[J]. Chemical Research in Chinese Universities, 2013, 29(6): 1134-1139.

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Synthesis and Biological Activity of Novel Anthranilic Diamides Containing N-Substituted Arylmethylene Moieties

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