5(3)-芳基-1H-3(5)-取代吡唑酰腙类化合物的合成、结构表征及其生物活性研究
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摘要
吡唑类化合物因其表现出高效、低毒等生物活性以及吡唑环上取代基多方位的变换而倍受人们的关注。酰腙类化合物因具有良好的生物和药物活性,一直是许多科研工作者的研究热点之一。
本文以对位取代苯乙酮及草酸二乙酯为起始原料,经Claisen酯缩合、Knorr环化、酯的氨基化反应,进而与芳香醛缩合,将上述生物活性良好的吡唑结构单元及腙的结构单元有机地结合在一起,设计并合成出30个目标化合物及9个中间体产物,其中20个目标化合物及4个中间体产物为未见文献报道的新化合物。
利用IR、1H NMR等现代测试手段对合成的所有目标产物及中间体的结构进行了表征。选取了代表性的化合物通过二维核磁谱图及核磁共振变温实验,对这类化合物中存在的互变异构现象进行了深入的研究,结果表明,在目标化合物中,trans异构体均占主要成分。
通过实验培养出一个中间产物和三个目标产物的有机单晶;应用中间产物与过渡金属离子(Cu2+)配位,得到了两个配合物。所有晶体均通过X-ray单晶衍射进行结构测定,并解出结构。
另外,对所合成的目标化合物还进行了初步生物活性的测试,研究了其在绿豆发芽过程中的影响。实验结果表明,当连吡唑环的苯基上没有取代基或者连接对甲氧基时,目标化合物对绿豆的发芽有促进作用;当连吡唑环的苯基上的取代基为硝基时,化合物对绿豆的发芽过程则表现为抑制作用。
Much attention has been paid to the study on the pyrazole derivatives due to their good biological activities such as effectively, low toxicity and the multi-changeable substituted groups on the pyrazole ring. On the other hand, hydrazones compounds have also attracted more and more attention according to their excellent biological and medical activities.
In this paper, 4-substituted acetophenone and diethyl oxalate were used as the starting materials, based on the methods of Claisen condensation, Knorr cyclization, amination of the ester, then reacted with the aromatic aldehydes, the two excellent biological groups discussed above-pyrazole and hydrazones, were connected together organically. 30 target compounds and 9 related intermediates were obtained, in which 20 target compounds and 4 intermediates are new compounds that have not yet been reported in the literatures.
All the target compounds and intermediates were characterized by IR, NMR. A representative compound was characterized in the 2D and difference thermal NMR test for further studying the structures of the target compounds and come to the conclusion that the trans isomer is the main component in the target compounds. In order to confirm the structures of the obtained organic compounds, three organic crystals of the target compounds, two new coordination compounds and a organic crystal from the reaction of the intermediates and the transition metal ion(Cu2+) were obtained and their structures were characterized by X-ray single crystal diffraction measurement.
Besides, primary biological activity experiments have been done to all the target compounds in order to study their effects on the germination process of mung bean. The preliminary results show that the target compounds have the effect of accelerating the germination process of mung bean when there are not any substituted groups or the substituted group is methyloxyl in the phenyl ring connecting to the pyrazole. However, when it is substituted by a nitro group in the phenyl ring, the target compounds have inhibiting effect on the germination process of mung bean.
本文以对位取代苯乙酮及草酸二乙酯为起始原料,经Claisen酯缩合、Knorr环化、酯的氨基化反应,进而与芳香醛缩合,将上述生物活性良好的吡唑结构单元及腙的结构单元有机地结合在一起,设计并合成出30个目标化合物及9个中间体产物,其中20个目标化合物及4个中间体产物为未见文献报道的新化合物。
利用IR、1H NMR等现代测试手段对合成的所有目标产物及中间体的结构进行了表征。选取了代表性的化合物通过二维核磁谱图及核磁共振变温实验,对这类化合物中存在的互变异构现象进行了深入的研究,结果表明,在目标化合物中,trans异构体均占主要成分。
通过实验培养出一个中间产物和三个目标产物的有机单晶;应用中间产物与过渡金属离子(Cu2+)配位,得到了两个配合物。所有晶体均通过X-ray单晶衍射进行结构测定,并解出结构。
另外,对所合成的目标化合物还进行了初步生物活性的测试,研究了其在绿豆发芽过程中的影响。实验结果表明,当连吡唑环的苯基上没有取代基或者连接对甲氧基时,目标化合物对绿豆的发芽有促进作用;当连吡唑环的苯基上的取代基为硝基时,化合物对绿豆的发芽过程则表现为抑制作用。
Much attention has been paid to the study on the pyrazole derivatives due to their good biological activities such as effectively, low toxicity and the multi-changeable substituted groups on the pyrazole ring. On the other hand, hydrazones compounds have also attracted more and more attention according to their excellent biological and medical activities.
In this paper, 4-substituted acetophenone and diethyl oxalate were used as the starting materials, based on the methods of Claisen condensation, Knorr cyclization, amination of the ester, then reacted with the aromatic aldehydes, the two excellent biological groups discussed above-pyrazole and hydrazones, were connected together organically. 30 target compounds and 9 related intermediates were obtained, in which 20 target compounds and 4 intermediates are new compounds that have not yet been reported in the literatures.
All the target compounds and intermediates were characterized by IR, NMR. A representative compound was characterized in the 2D and difference thermal NMR test for further studying the structures of the target compounds and come to the conclusion that the trans isomer is the main component in the target compounds. In order to confirm the structures of the obtained organic compounds, three organic crystals of the target compounds, two new coordination compounds and a organic crystal from the reaction of the intermediates and the transition metal ion(Cu2+) were obtained and their structures were characterized by X-ray single crystal diffraction measurement.
Besides, primary biological activity experiments have been done to all the target compounds in order to study their effects on the germination process of mung bean. The preliminary results show that the target compounds have the effect of accelerating the germination process of mung bean when there are not any substituted groups or the substituted group is methyloxyl in the phenyl ring connecting to the pyrazole. However, when it is substituted by a nitro group in the phenyl ring, the target compounds have inhibiting effect on the germination process of mung bean.
引文
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