含二茂铁基新型Schiff碱配体及其过渡金属配合物的合成、表征及抑菌活性研究
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摘要
由于二茂铁及其衍生物的独特结构,它们表现出许多特殊的性质,其应用已经涉及催化、助燃剂、医学等多个领域。含二茂铁基Schiff碱是一类重要的新型配体,由于其过渡金属配合物具有一定的生理活性,可作为抗菌、抗癌等药物,具有很大的发展前景,因而这类新型配体及其过渡金属配合物的合成、表征及生物活性研究越来越引起人们的重视。本文设计合成了两个系列含二茂铁基Schiff碱配体及其过渡金属配合物,研究了部分化合物的抑菌活性,主要开展以下五个方面的工作:
1、将1,1’-双乙酰基二茂铁双肼腙分别与邻羟基苯乙酮、水杨醛、2,4-二羟基苯甲醛、邻羟基萘醛、邻香草醛、5-溴水杨醛、3,5-二溴水杨醛、5-氯水杨醛按1:2的比例反应,制备了8个1,1’-取代的二茂铁Schiff碱新配体,并对其结构进行了表征。
2、用邻羟基萘醛缩双肼腙配体、邻香草醛缩双肼腙配体、5-溴水杨醛缩双肼腙配体与过渡金属Cu(II)、Co(II)、Ni(II)、Zn(II)的醋酸盐反应,合成了12个新型含二茂铁的Schiff碱过渡金属配合物,对其进行了结构表征。
3、在无水甲醇中,单乙酰基二茂铁分别与烟酰肼、异烟酰肼以1:1的比例缩合生成酰腙,双乙酰基二茂铁分别与烟酰肼、异烟酰肼以1:2的比例缩合生成双酰腙,合成了4个未见文献报道的单、双取代二茂铁酰腙类Schiff碱配体,并对其结构进行了表征。
4、用单乙酰基二茂铁异烟酰腙、单乙酰基二茂铁烟酰腙、1,1’-双乙酰基二茂铁异烟酰腙、1,1’-双乙酰基二茂铁烟酰腙与过渡金属Cu(II)、Co(II)、Ni(II)、Zn(II)的氯化物反应,合成了16个新型五元杂环酰腙Schiff碱过渡金属配合物,并对其结构进行了表征。
5、选择邻羟基萘醛缩双肼腙配体和邻香草醛缩双肼腙配体及其过渡金属Cu(II)、Co(II)、Ni(II)、Zn(II)配合物,对它们的抑菌活性进行了初步的测试,对所得结果进行分析比较。结果表明新合成的配体及其配合物均有明显的抑菌活性,与配体相比,配合物的抑菌活性有显著的提高。
Because of their unique structures, ferrocene and its derivatives behaved many special properties, and they have been used in many areas, such as catalysis, assistant combustion reagents, medicine, et al. Ferrocenyl Schiff bases are one kind of important ferrocene derivations, their transtion metal complexes have shown good biological activities against several types of bacteria and cancers. Their interesting applicantion attracted us to continue our previous studies. In this paper, two series of ferrocenyl Schiff base and their transtion metal complexes have been synthesized. They have been screened for their antibacterial activity.
1). Eight novel ferrocenyl Schiff base(H2L1~H2L8) have been prepared by the condensation of 1,1’-diacetylferrocene dihydrazone with 2-hydroxyacetophenon, salicylaldehyde, 2,4-dihydroxy benzaldehyde, 2-hydroxy naphthaldehyde, o-vanillin, 5-bromo sailcyladehyde, 3,5-dibromosailcyladehyde or 5-chloro sailcyladehyde respectively. Their structures were characterized.
2). H2L4,H2L5 and H2L6 were used as ligands to react with cobalt(II), copper(II), nickel(II) and zinc(II) metals acetates respectively. Their structures were characterized.
3). Four new ferrocenyl Schiff base(L9~L12) have been prepared by the condensation of acetylferrocene or 1,1’-diacetylferrocene with nicotinic hydrazide or isonicotinoyl hydrazide. Their structures were characterized.
4). Ferrocenyl Schiff base (L9~L12) were used as ligands to react with cobalt(II), copper(II), nickel(II) and zinc(II) metals chlorides respectively. Their structures were characterized.
5). The ligands (H2L4,H2L5) and their transition metal complexes have been screened for their antibacterial activities. The results synthesized in this paper show that they were found potentially antibacterial activity. The metal complexes to be more antibacterial than the ligands.
1、将1,1’-双乙酰基二茂铁双肼腙分别与邻羟基苯乙酮、水杨醛、2,4-二羟基苯甲醛、邻羟基萘醛、邻香草醛、5-溴水杨醛、3,5-二溴水杨醛、5-氯水杨醛按1:2的比例反应,制备了8个1,1’-取代的二茂铁Schiff碱新配体,并对其结构进行了表征。
2、用邻羟基萘醛缩双肼腙配体、邻香草醛缩双肼腙配体、5-溴水杨醛缩双肼腙配体与过渡金属Cu(II)、Co(II)、Ni(II)、Zn(II)的醋酸盐反应,合成了12个新型含二茂铁的Schiff碱过渡金属配合物,对其进行了结构表征。
3、在无水甲醇中,单乙酰基二茂铁分别与烟酰肼、异烟酰肼以1:1的比例缩合生成酰腙,双乙酰基二茂铁分别与烟酰肼、异烟酰肼以1:2的比例缩合生成双酰腙,合成了4个未见文献报道的单、双取代二茂铁酰腙类Schiff碱配体,并对其结构进行了表征。
4、用单乙酰基二茂铁异烟酰腙、单乙酰基二茂铁烟酰腙、1,1’-双乙酰基二茂铁异烟酰腙、1,1’-双乙酰基二茂铁烟酰腙与过渡金属Cu(II)、Co(II)、Ni(II)、Zn(II)的氯化物反应,合成了16个新型五元杂环酰腙Schiff碱过渡金属配合物,并对其结构进行了表征。
5、选择邻羟基萘醛缩双肼腙配体和邻香草醛缩双肼腙配体及其过渡金属Cu(II)、Co(II)、Ni(II)、Zn(II)配合物,对它们的抑菌活性进行了初步的测试,对所得结果进行分析比较。结果表明新合成的配体及其配合物均有明显的抑菌活性,与配体相比,配合物的抑菌活性有显著的提高。
Because of their unique structures, ferrocene and its derivatives behaved many special properties, and they have been used in many areas, such as catalysis, assistant combustion reagents, medicine, et al. Ferrocenyl Schiff bases are one kind of important ferrocene derivations, their transtion metal complexes have shown good biological activities against several types of bacteria and cancers. Their interesting applicantion attracted us to continue our previous studies. In this paper, two series of ferrocenyl Schiff base and their transtion metal complexes have been synthesized. They have been screened for their antibacterial activity.
1). Eight novel ferrocenyl Schiff base(H2L1~H2L8) have been prepared by the condensation of 1,1’-diacetylferrocene dihydrazone with 2-hydroxyacetophenon, salicylaldehyde, 2,4-dihydroxy benzaldehyde, 2-hydroxy naphthaldehyde, o-vanillin, 5-bromo sailcyladehyde, 3,5-dibromosailcyladehyde or 5-chloro sailcyladehyde respectively. Their structures were characterized.
2). H2L4,H2L5 and H2L6 were used as ligands to react with cobalt(II), copper(II), nickel(II) and zinc(II) metals acetates respectively. Their structures were characterized.
3). Four new ferrocenyl Schiff base(L9~L12) have been prepared by the condensation of acetylferrocene or 1,1’-diacetylferrocene with nicotinic hydrazide or isonicotinoyl hydrazide. Their structures were characterized.
4). Ferrocenyl Schiff base (L9~L12) were used as ligands to react with cobalt(II), copper(II), nickel(II) and zinc(II) metals chlorides respectively. Their structures were characterized.
5). The ligands (H2L4,H2L5) and their transition metal complexes have been screened for their antibacterial activities. The results synthesized in this paper show that they were found potentially antibacterial activity. The metal complexes to be more antibacterial than the ligands.
引文
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