【作者】 高莹；

【导师】 朱红军；

【作者基本信息】 南京工业大学 ， 应用化学， 2003， 硕士

【摘要】 含氮杂环化合物在医药、农药的研究开发中占据十分重要的地位，其中毗哗烷酮类化合物因其对y一氨基丁酸氨基转移酶(GABA．T)有强烈的抑制活性，及对5一脂氧酶具有抑制作用等，在医药中有一定的应用，也可以作为农药的先导结构。同时，3．芳基．2．丙烯酸酯因其具有多个反应中心，而显出其重要和特殊的化学性质，在很多有机合成及生物代谢过程中起着承上启下的中『白J体的作用。为此我们从3．芳基．2．丙烯酸酯的合成丌始，对具有生物活性的吡唑烷酮类化合物的合成进行了研究，合成了系列二芳基吡唑烷酮新化合物，并进行了生物活性方面的初步研究。 本文利用取代苯甲醛(RC6tt4CI~{O，R=H，F or OPh)与乙酸酐在无水碳酸钾的催化作用下，发生Perkin反应，合成了3．(4．氟苯基)．2．丙烯酸和3．(3一苯氧基苯基)．2．丙烯酸。反应转化率在50～60％左右。 所合成得到的产品经元素分析、IR和。H．NMR分析证明与预期结构相符。 3．芳基．2．丙烯酸和无水乙醇在对甲苯磺酸的催化作用下反应生成3．芳基．2一丙烯酸酯 (3．苯基．2．丙烯酸乙酯，3．(4．甲基苯基)．2．丙烯酸乙酯，3．(4．甲氧基苯基)．2．丙烯酸乙酯，3．(3，4．二甲氧基苯基)．2．丙烯酸乙酯，3．(4．氟苯基)．2．丙烯酸乙酯，3．(4．氯苯基)．2．丙烯酸乙酯，3-(3．硝基苯基)．2．丙烯酸乙酯，3．(4．硝基苯基)-2．丙烯酸乙酯，3．(3．苯氧基苯基)．2．丙烯酸乙酯，3．(2，3．二甲氧基苯基)．2．丙烯酸乙酯)，反应的转化率在70％以上。所合成得到的产品3．芳基．2．丙烯酸酯经元素分析、IR、。H．NMR分析证明与预期结构相符。 3．芳基．2一丙烯酸酯与芳基肼在醇钠的催化作用下，反应可生成1，5．二芳基．3．吡唑烷酮，产率在55％以上。所合成得到的产品--1，5．二芳基．3．吡哗烷酮(1，5．二苯基．3．吡唑烷酮，1．苯基．5．(4．甲基)．3一吡哗烷酮，1．苯基．5．(4．甲氧基)．3．吡哗烷酮，2一苯基．5．(3，4．二甲氧基)．3．吡哗烷酮，1．苯基．5．(4．氟)．3．毗哗烷酮，1．苯基-5．(4．氯)．3．吡哗烷酮，1．苯基．5．(3．苯氧基)．3．吡哗烷酮)经元素分析、IR、。H-NMR、UV、MS等分析，证明所合成的产品的结构与预期结构相符。<WP=7> 所合成的系列1，5．二芳基．3．吡唑烷酮经全国南方农药创制中心检测，结果表明：所测试的7个1，5．二芳基．3．吡唑烷酮样品，对小菜蛾、蚕豆蚜、朱砂叶螨3种靶标具有活性，但活性较低；对小麦白粉病菌在活体1000ppm剂量下活性等级为D级；对小麦纹枯病菌、小麦赤霉病菌、油菜菌核病菌的抑制活性较佳，大部分为A级，达到复筛的要求。有关生物活性试验证明了吡唑烷酮类化合物确实具有一定的生物活性，吡唑烷酮可作为先导结构而进行研究。更多还原

【Abstract】 Heterocyclic compounds as medicines and pesticides has been developed mostquickly and has become the new trend in the development. In the new developedmedical and pesticidal heterocyclic compounds are the most important domain3-Pyrazolidinones can increase GABA (3,-aminobutyric acid) level in brains ofbeasties, and show anticonvulsant activities of the GABA-T inhibitor.3-Arylpropenates are the one kind of the most important intermediates in thefields of the organic synthesize and which play essential roles in somebiosynthetic and metabolic pathways. In addition, 3-arylpropenates themselveshave attracted increasing interest in connection with their activity as potentinhibitorsof proteolytic enzymes, inhibitors of A4 hydrolase,photopolymerization initiators, and precursors in the asymmetric synthesis of-hydroxy carboxylic acids. In this thesis, the method for preparation of bioactivitycompounds 1,5-diaryl-3- pyrazolidinones has been studied. Their bioactivity hasalso been measured.Perkin reaction is an important traditional 3-arylpropenoic acid synthesismethod. The reaction of benzaldehyde or its analogs and acetic anhydride underthe catalysis of anhydrous potassium carbonate has been studied. 3-arylpropenoicacids {3-(4-fluorophenyl) propenoic acid, 3-(3-benoxyphenyl) propenoic acid }have been synthesized. Their yields are about 50%. And the structures of theseproductions have been confirmed by elemental analyst, IR, 1H-NMR whichshowed that they are 3-arylpropenoic acidsA series of 3-arylpropenates {3-(3,4-dimethoxyphenyl) propenate ,<WP=9>3-(4-fluorophenyl) propenate, 3-(4-chlorophenyl) propenate, 3-(3-benoxyphenyl)propenate et. } have been synthesized by reaction of 3-arylpropenoic acids andabsolute alcohol under the catalysis of p-toluene sulfuric acid. The yield of thisreaction is about 70%. The structures of these productions have been confirmedby elemental analyst, IR, lH-NMR.3-arylpropenates were reacted with hydrazine catalysed by sodiummethylate, which gained 1,5-diaryl-3-pyrazolidinones. Their yields are about50-80%. The structures of these productions have been confirmed by elementalanalyst, IR, 1H-NMR, UV, MS which showed that the structures of thesecompounds are the same as desired.The bioactivitis of 1,5-diaryl-3-pyrazolidinones in this thesis were tested,and it was found that some of them showed good bioactivity更多还原