苯氧乙酸类化合物及其金属配合物的合成和生物活性的研究
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摘要
苯氧乙酸类化合物是一类活性很高、应用很广的苯氧羧酸化合物,主要用做除草剂和生长调节剂。浓度低时,可以作为农作物的生长调节剂,提高作物的成花率、授粉率和产量,促进农作物的成熟,保证农作物的质量；浓度高时,可以防除杂草,属激素型除草剂。此外,苯氧乙酸类化合物还是医药、农药合成的重要中间体,同时具有矿石浮选抑制性能。因此,近年来苯氧乙酸类化合物受到人们广泛的关注。我们在大量查阅国内外文献的基础上,对苯氧乙酸类化合物进行了研究,设计并合成了四个苯氧乙酸类化合物和五个H3BTA的金属配合物,并对其结构和抑菌活性进行了研究。具体工作如下：
1.以3,5-二羟基苯甲酸、2,6-二羟基异烟酸、1,2,3-三羟基苯作为原料,根据Williamson Synthesis原理分别与一氯乙酸在强碱性条件下加入相转移催化剂合成了3种苯氧乙酸类化合物；另外,用双酚A和溴乙酸乙酯进行取代反应后,得到的产物在碱性条件下再进行水解得到2,2-二(4-氧乙酸基苯基)丙烷；它们的结构通过元素分析、IR、1HNMR等手段进行了表征且得到证实。
2.以合成的1,2,3-三氧乙酸基苯作为配体,通过降温法合成了5个苯氧乙酸的金属配合物,其结构经X射线单晶衍射进行了表征并对它的配位特点进行了描述。
3.在不同浓度下用滤纸片法对1,3,5-二氧乙酸基苯甲酸、2-氧乙酸基-6-羟基异烟酸、1,2,3-三氧乙酸基苯、2,2-二(4-氧乙酸基苯基)丙烷,配合物[Co1.5(BTA)·6H2O]6H2O, [Co3(BTA)2(4,4'-bipy)(H2O)8]·8H2O, [Co(HBTA)(2,2'-bipy) (H2O)2]·2H2O, [Co(HBTA)(phen)(H2O)2]·H2O, [Cu(HBTA)(phen)(H2O)2]H2O对枯草芽抱杆菌、大肠杆菌、金黄色葡萄球菌的抑制效果进行了测定。结果表明,合成的新型苯氧乙酸类化合物及金属配合物具有一定的抑菌活性。
Phenoxyacetate compounds have fierceness bioactivities and wide application which belong to pHenoxy carboxylic acid compounds. Mostly, they are used as herbicide and plant growth regulator. At a low concentration, phenoxyacetate compounds play an important part in regulating crops'growth to enhance their flower formation rate, pollination rate, production, quality and hastened maturity. At a high concentration, phenoxyacetate compounds play as hormone type herbicides. In addition, phenoxyacetate compounds not only are the important intermediate in the synthesis of medicine and pesticide, but also have the depression on mineral. According to the above reasons, phenoxyacetate compounds are receiving much attention recently. On the foundation of numerous references, we designed and synthesized four phenoxyacetate compounds and five metal coordination polymers. Moreover, their structure and antibacterial were studied. The work mainly been engaged in is as follows:
1. According to the principle of Williamson Synthesis, in order to synthesis the novel pHenoxyacetate compounds, a synthetic method was investigated by the treatment of 3,5-dihydroxybenzoic acid, citrazinic acid, pyrogallic acid and chloroacetic under substitution reaction on the strong alkali and the pHase transfer catalyst was added. The intermediate which was obtained through the substitution reaction of BispHenol A and ethyl bromoacetate hydrolyzed to get 2,2-bis(4-carboxy-methoxyphenyl)propane under the alkaline condition. And the structure of target compounds was confirmed by Elemental Analysis, IR and 1H NMR.
2. Through cooling method, the synthetic PH-(OCH2COOH)3 was used as ligand method to construct five coordination polymers which were characterized by X-ray single crystal diffraction and their coordination features were described.
3. The bacteriostasis activity of synthetic phenoxyacetate compounds and the metal coordination polymers against bacillus subtilis, escherichia coli, staphylococcus aureus was studied by the filter paper method. And the results show they have some inhibitory effects.
1.以3,5-二羟基苯甲酸、2,6-二羟基异烟酸、1,2,3-三羟基苯作为原料,根据Williamson Synthesis原理分别与一氯乙酸在强碱性条件下加入相转移催化剂合成了3种苯氧乙酸类化合物；另外,用双酚A和溴乙酸乙酯进行取代反应后,得到的产物在碱性条件下再进行水解得到2,2-二(4-氧乙酸基苯基)丙烷；它们的结构通过元素分析、IR、1HNMR等手段进行了表征且得到证实。
2.以合成的1,2,3-三氧乙酸基苯作为配体,通过降温法合成了5个苯氧乙酸的金属配合物,其结构经X射线单晶衍射进行了表征并对它的配位特点进行了描述。
3.在不同浓度下用滤纸片法对1,3,5-二氧乙酸基苯甲酸、2-氧乙酸基-6-羟基异烟酸、1,2,3-三氧乙酸基苯、2,2-二(4-氧乙酸基苯基)丙烷,配合物[Co1.5(BTA)·6H2O]6H2O, [Co3(BTA)2(4,4'-bipy)(H2O)8]·8H2O, [Co(HBTA)(2,2'-bipy) (H2O)2]·2H2O, [Co(HBTA)(phen)(H2O)2]·H2O, [Cu(HBTA)(phen)(H2O)2]H2O对枯草芽抱杆菌、大肠杆菌、金黄色葡萄球菌的抑制效果进行了测定。结果表明,合成的新型苯氧乙酸类化合物及金属配合物具有一定的抑菌活性。
Phenoxyacetate compounds have fierceness bioactivities and wide application which belong to pHenoxy carboxylic acid compounds. Mostly, they are used as herbicide and plant growth regulator. At a low concentration, phenoxyacetate compounds play an important part in regulating crops'growth to enhance their flower formation rate, pollination rate, production, quality and hastened maturity. At a high concentration, phenoxyacetate compounds play as hormone type herbicides. In addition, phenoxyacetate compounds not only are the important intermediate in the synthesis of medicine and pesticide, but also have the depression on mineral. According to the above reasons, phenoxyacetate compounds are receiving much attention recently. On the foundation of numerous references, we designed and synthesized four phenoxyacetate compounds and five metal coordination polymers. Moreover, their structure and antibacterial were studied. The work mainly been engaged in is as follows:
1. According to the principle of Williamson Synthesis, in order to synthesis the novel pHenoxyacetate compounds, a synthetic method was investigated by the treatment of 3,5-dihydroxybenzoic acid, citrazinic acid, pyrogallic acid and chloroacetic under substitution reaction on the strong alkali and the pHase transfer catalyst was added. The intermediate which was obtained through the substitution reaction of BispHenol A and ethyl bromoacetate hydrolyzed to get 2,2-bis(4-carboxy-methoxyphenyl)propane under the alkaline condition. And the structure of target compounds was confirmed by Elemental Analysis, IR and 1H NMR.
2. Through cooling method, the synthetic PH-(OCH2COOH)3 was used as ligand method to construct five coordination polymers which were characterized by X-ray single crystal diffraction and their coordination features were described.
3. The bacteriostasis activity of synthetic phenoxyacetate compounds and the metal coordination polymers against bacillus subtilis, escherichia coli, staphylococcus aureus was studied by the filter paper method. And the results show they have some inhibitory effects.
引文
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