Design, Synthesis and Biological Activities of Novel N -Aryl-1 H -pyrazole-5-carboxylate Derivatives
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doi: 10.1007/s40242-019-9274-3
Design, Synthesis and Biological Activities of Novel N-Aryl-1H-pyrazole-5-carboxylate Derivatives ZHANG Xiulan1*, ZHANG Huan1, MA Jinlong2, YU Shujing2 and LI Zhengming2* 1. College of Science, Tianjin University of Science & Technology, Tianjin 300457, P. R. China; 2. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China Abstract In an attempt to search for potent fungicide, a series of novel N-aryl-1H-pyrazole-5-carboxylate derivatives was designed and synthesized. Their chemical structures were characterized by 1H NMR spectra and high resolution mass spectrometry(HRMS). The preliminary bioassay results indicated that some target compounds displayed better fungicidal activities against certain fungi at 50 μg/mL or favorable antitumor activities at 5 μg/mL compared with chlorothalonil and 5-fluorouracil, respectively. The structure-activity relationship demonstrated that the introduction of ester group and amide bond was favorable to the improvement of activities against Physalospora piricola and Phytophthora capsici. Keywords N-Aryl-1H-pyrazole-5-carboxylate; Fungicidal activity; Antitumor activity
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Introduction
Plant pathogenic fungi are commonly found in the environment. Twenty thousand different fungal species need to live on plant hosts to extend their life cycle, which brings serious harm to agricultural production. Fungicides have the characteristics of fast response, high efficiency, low cost and easy to use, so the main step of preventing and controlling crop diseases is still using fungicides. Today in China, there are some problems existing in this field, such as old fungicides, increasing resistance and high residue, so it needs to constantly deve-
lop fungicides with new mechanism and independent intellectual property rights. Nitrogenous heterocyclic compounds with unique structural characteristic, physiological function and high activity have been widely used in the synthesis of medicine and pesticide. Pyrazole derivatives especially have become a research hot spot in the field of agricultural chemicals due to their good herbicidal activity [1―2] , insecticidal activity [3―5] , fungicidal activity [6―8] , antiviral activity [9―10] , antitumor activity[11―13] and so on. It was reported that N-pyridyl-1H-pyrazolecarbohydrazide derivatives A[14](Scheme 1) exhibited good
Scheme 1 Design strategy of target compounds ——————————— *Corresponding authors. Email: [email protected]; [email protected] Received October 10, 2019; accepted November 11, 2019. Supported by the Scientific Research Program of Tianjin Municipal Education Commission, China(No.2018KJ114). © Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH
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Chem. Res. Chinese Universities
inhibitory activity against some fungi at 50 μg/mL. Further optimization of the structure is expected to obtain potent fungicide. It is an effective method to optimize lead compou
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