Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles
Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles
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DOI：
10.1016/j.ejmech.2005.03.021
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发表时间：
2005-09-01
影响因子：
6.7
通讯作者：
Singh, SP
中科院分区：
文献类型：
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作者：
Kumar, V;Aggarwal, R;Singh, SP
用几种杂芳肼（2a-e）在回流乙醇中处理1,1,1-三氟甲基-3-氰基-3-苯基丙烷(1)，得到1-杂芳基-5-氨基-4-苯基-3-三氟甲基吡唑(4)，具有区域选择性。利用核磁共振C-13和F-19谱法确定了三氟甲基在3位的位置。该反应通过腙的中间体进行，该中间体在室温下进行反应，在一个案例（3e）中被分离和表征。测定了化合物3e和4对6种革兰氏阳性菌和3种革兰氏阴性菌的抑菌性能。两种化合物1-（苯并噻唑-2′-酰基）5-氨基-4-苯基-3-三氟甲基吡唑（4a）和1-（6′-甲基苯并噻唑-2′-酰基）-5-氨基-4-苯基-3-三氟甲基吡唑（4b）显示出与商业抗生素相当的抗菌活性。(c) 2005 Elsevier SAS。版权所有。
Treatment of 1,1,1-trifluoromethyl-3-cyano-3-phenylpropanone(1) with several heteroarylhydrazines (2a-e) in refluxing ethanol affords 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles (4) in a regioselective manner. The location of trifluoromethyl group at position-3 was established by a combined use of C-13 and F-19 NMR spectroscopy. The reaction proceeds through the intermediacy of the hydrazone which was isolated and characterized in one case (3e) by performing the reaction at room temperature. The compounds 3e and 4 were tested for their antibacterial property against six Gram-positive and three Gram-negative bacteria. Two compounds, namely 1-(benzothiazol-2'-yl)5-amino-4-phenyl-3-trifluoromethylpyrazole (4a) and 1-(6'-methylbenzothiazol-2'-yl)-5-amino-4-phenyl-3-trifluoromethylpyrazole (4b) have displayed antibacterial activity comparable to the commercial antibiotics. (c) 2005 Elsevier SAS. All rights reserved.