Xiaobo Liu, Shan Xu, Yinhua Xiong
Feb 1, 2017
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Abstract
3-phenyl-1H-pyrazole (1) is an important intermediate for the synthesis of many biologically active compounds. It was synthesized from acetophenone (2) and hydrazine through two steps including Knoevenagel condensation, Cyclization reaction reaction. In this paper, three novel 3-phenyl-1H-pyrazole derivatives were prepared. The structure were confirmed by MS and 1 H NMR. Furthermore, the synthetic method was optimized. The total yield of the two steps were 80%. Introduction In today's society, cancer is a serious threat to human health and life, although the traditional method of treatment of cancer is simple and quick, but there is a big drawback [1] . Tumor molecular targeted therapy using tumor cells and normal cells between the molecular biology of the differences, blocking the signal transduction pathway, blocked receptors, inhibition of angiogenesis and other methods specific role in tumor cell targets, specific Inhibit tumor cell proliferation, invasion and metastasis, and promote its apoptosis [2-3] . Because of the specificity of the target, molecular targeted therapy is more selective than traditional chemotherapy and has less side effects. Therefore, molecular targeted therapy for cancer has been widely concerned in cancer therapy because of its safe and high efficiency [4-5] . In recent years, there are many small molecular targeted anticancer drugs have been reported. Among them, 3-phenyl-1H-pyrazole (1) is an significant intermediate for the synthesis of many biologically active compounds. Therefore, design and synthesis of compound 1 derivative as small molecule inhibitors played a essential role in the study of anticancer. Many compound 1 derivatives which exhibited potential biological activities, such as methyl 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)phenyl(methoxy)carbamate (3) [6] , N-((1H-pyrazol-1-yl)methyl)-N-(3-chloroprop-1-en-2-yl)-2,6-dimethylbenzenamine (4) [7] , methyl 3-(4-chlorophenyl)-4-methyl-1-((4-(trifluoromethyl)phenyl)carbamoyl)-4,5-dihydro-1H-pyrazole-4carboxylate (5) [8] , ethyl 3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazole-4-carboxylate (6) [9] , 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (7) [10] , these compound 1 derivatives showed biological activity. Most of the synthetic methods of compound 1 which reported in the literature have the drawbacks such as longer synthetic route, lower yield and harmful to environment. Therefore, the optimization of the synthetic route and methods of compound 1 is necessary. In this study, we prepared three kinds of compound 1 derivatives, and design and optimize the method of the sythesis of compound 1, making it more suitable for industrial production. The structures of representative compounds were shown in Fig. 1. 7th International Conference on Education, Management, Computer and Medicine (EMCM 2016) Copyright © 2017, the Authors. Published by Atlantis Press. This is an open access article under the CC BY-NC license (http://creativecommons.org/licenses/by-nc/4.0/). Advances in Computer Science Research, volume 59