三齿配体杂环五配位有机锡席夫碱配合物的合成及生物活性研究
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摘要
有机锡Schiff碱配合物具有广泛的生物活性,特别是其中一部分物质具有抗菌、抗癌活性,因而近年来对该类物质的研究越来越引人注目。因此合成具有多种结构类型的有机锡化合物对于系统研究其生物活性特别是抗菌、抗癌活性,进一步探讨其构效关系具有重要意义。本文设计合成了三个系列杂环五配位有机锡(IV) Schiff碱配合物,并研究了此类配合物的抗菌、抗癌生物活性。主要包括以下五部分的工作:
1、以水杨醛、邻香草醛、邻羟基萘甲醛、2,4-二羟基苯甲醛、邻羟基苯乙酮、5-溴水杨醛、3,5-二溴水杨醛分别与邻氨基苯酚按1:1的比例在无水乙醇中反应,制备了7种邻氨基苯酚类Schiff碱;以水杨醛、邻香草醛、邻羟基萘甲醛、2,4-二羟基苯甲醛分别与邻氨基硫酚按1:1的比例在无水乙醇中反应,制备了4种邻氨基硫酚类Schiff碱;以水杨醛、邻香草醛、邻羟基萘甲醛分别与邻氨基苯甲酸按1:1的比例在无水乙醇中反应,制备了3种邻氨基苯甲酸类Schiff碱,并对合成的Schiff碱配体的结构进行了表征。
2、以二苄基二氯化锡、二苯基二氯化锡、二正丁基二氯化锡分别与邻氨基苯酚类Schiff碱配体在无水甲醇溶剂中反应,制备了21种新型杂环五配位有机锡(IV)邻氨基苯酚类Schiff碱配合物,并对其结构进行了表征。
3、以二苄基二氯化锡、二苯基二氯化锡、二正丁基二氯化锡分别与邻氨基硫酚类Schiff碱配体在无水甲醇溶剂中反应,制备了12种新型杂环五配位有机锡(IV)邻氨基硫酚类Schiff碱配合物,并对其结构进行了表征。
4、以二苄基二氯化锡、二苯基二氯化锡、二正丁基二氯化锡分别与邻氨基苯甲酸类Schiff碱配体在无水甲醇溶剂中反应,制备了9种新型杂环五配位有机锡(IV)邻氨基苯甲酸类Schiff碱配合物,并对其结构进行了表征。
5、分别对合成的目标化合物1-12号进行了抗菌活性和抗癌活性研究,并初步探讨了生物活性同有机锡配合物的结构构效之间的关系。
There has been growing interested in Organotin(IV) complexes because of their extensive bioactivities, especially anti–tumour activity, so its have recently increased attention. It is very important to synthesis different types of organotin complexes with different structures. For it can provide much knowledge about the antibacterial and antitumour activities of organotin complexes, and it also can help us to study the relationship between the bioactivities and the structures of the organotin compounds. In this paper, three series of heterocyclic pentcoordinated organotin(Ⅳ) Schiff base complexes have been synthesized, its antibacterial and antitumour activities were also investigated.
1. Seven aminophenol Schiff bases have been synthesized by the reaction of salicylaldehyde, o–vanillin, 2-hydroxy-1-naphthaldehyde, 2,4-dihydroxybenzaldehyde, o-hydroxyacetophenone, 5-bromine salicylaldehyde, 3,5-dibromine salicylaldehyde with o-aminophenol in anhydrous ethanol respectively; Four aminobenzenethiol Schiff bases have been synthesized by the reaction of salicylaldehyde, o–vanillin, 2-hydroxy-1-naphthaldehyde, 2,4-dihydroxybenzaldehyde with o-aminobenzenethiol in hydrous ethanol respectively. Three aminobenzoic acid Schiff bases have been synthesized by reaction of salicylaldehyde, o–vanillin, 2-hydroxy-naphthaldehyde with o-aminobenzoic acid in an hydrous-ethanol respectively. Their structures were characterized.
2. Dibenzyltin, diphenyltin dichloride and di–n–butyltin dichloride have been synthesized by the literature method. Twenty-one novel heterocyclic pentcoordinate organotin(Ⅳ) Schiff base complexes have been synthesized by the reaction of dibenzyltin dichloride, diphenyltin dichloride and di–n–butyltin dichloride with o -aminophenol Schiff bases in anhydrous methanol. Their structures were characterized.
3. Twelve novel heterocyclic pentcoordinate organotin(Ⅳ) Schiff base complexes have been synthesized by the reaction of dibenzyltin dichloride, diphenyltin dichloride and di–n–butyltin dichloride with the o-aminobenzenethiol Schiff bases in anhydrous methanol. Their structures were characterized.
4. Nine novel heterocyclic pentcoordinated organotin(Ⅳ) Schiff base complexes have been synthesized by the reaction of dibenzyltin dichloride, diphenyltin dichloride and di–n–butyltin dichloride with o-aminobenzoic acid Schiff bases in anhydrous methanol. Their structures were characterized.
5. The antibacterial and antitumour activities of the objective compounds 1-12 were determined. The relationships between the bioactivities and the structures of the organotin compounds were also been studied.
1、以水杨醛、邻香草醛、邻羟基萘甲醛、2,4-二羟基苯甲醛、邻羟基苯乙酮、5-溴水杨醛、3,5-二溴水杨醛分别与邻氨基苯酚按1:1的比例在无水乙醇中反应,制备了7种邻氨基苯酚类Schiff碱;以水杨醛、邻香草醛、邻羟基萘甲醛、2,4-二羟基苯甲醛分别与邻氨基硫酚按1:1的比例在无水乙醇中反应,制备了4种邻氨基硫酚类Schiff碱;以水杨醛、邻香草醛、邻羟基萘甲醛分别与邻氨基苯甲酸按1:1的比例在无水乙醇中反应,制备了3种邻氨基苯甲酸类Schiff碱,并对合成的Schiff碱配体的结构进行了表征。
2、以二苄基二氯化锡、二苯基二氯化锡、二正丁基二氯化锡分别与邻氨基苯酚类Schiff碱配体在无水甲醇溶剂中反应,制备了21种新型杂环五配位有机锡(IV)邻氨基苯酚类Schiff碱配合物,并对其结构进行了表征。
3、以二苄基二氯化锡、二苯基二氯化锡、二正丁基二氯化锡分别与邻氨基硫酚类Schiff碱配体在无水甲醇溶剂中反应,制备了12种新型杂环五配位有机锡(IV)邻氨基硫酚类Schiff碱配合物,并对其结构进行了表征。
4、以二苄基二氯化锡、二苯基二氯化锡、二正丁基二氯化锡分别与邻氨基苯甲酸类Schiff碱配体在无水甲醇溶剂中反应,制备了9种新型杂环五配位有机锡(IV)邻氨基苯甲酸类Schiff碱配合物,并对其结构进行了表征。
5、分别对合成的目标化合物1-12号进行了抗菌活性和抗癌活性研究,并初步探讨了生物活性同有机锡配合物的结构构效之间的关系。
There has been growing interested in Organotin(IV) complexes because of their extensive bioactivities, especially anti–tumour activity, so its have recently increased attention. It is very important to synthesis different types of organotin complexes with different structures. For it can provide much knowledge about the antibacterial and antitumour activities of organotin complexes, and it also can help us to study the relationship between the bioactivities and the structures of the organotin compounds. In this paper, three series of heterocyclic pentcoordinated organotin(Ⅳ) Schiff base complexes have been synthesized, its antibacterial and antitumour activities were also investigated.
1. Seven aminophenol Schiff bases have been synthesized by the reaction of salicylaldehyde, o–vanillin, 2-hydroxy-1-naphthaldehyde, 2,4-dihydroxybenzaldehyde, o-hydroxyacetophenone, 5-bromine salicylaldehyde, 3,5-dibromine salicylaldehyde with o-aminophenol in anhydrous ethanol respectively; Four aminobenzenethiol Schiff bases have been synthesized by the reaction of salicylaldehyde, o–vanillin, 2-hydroxy-1-naphthaldehyde, 2,4-dihydroxybenzaldehyde with o-aminobenzenethiol in hydrous ethanol respectively. Three aminobenzoic acid Schiff bases have been synthesized by reaction of salicylaldehyde, o–vanillin, 2-hydroxy-naphthaldehyde with o-aminobenzoic acid in an hydrous-ethanol respectively. Their structures were characterized.
2. Dibenzyltin, diphenyltin dichloride and di–n–butyltin dichloride have been synthesized by the literature method. Twenty-one novel heterocyclic pentcoordinate organotin(Ⅳ) Schiff base complexes have been synthesized by the reaction of dibenzyltin dichloride, diphenyltin dichloride and di–n–butyltin dichloride with o -aminophenol Schiff bases in anhydrous methanol. Their structures were characterized.
3. Twelve novel heterocyclic pentcoordinate organotin(Ⅳ) Schiff base complexes have been synthesized by the reaction of dibenzyltin dichloride, diphenyltin dichloride and di–n–butyltin dichloride with the o-aminobenzenethiol Schiff bases in anhydrous methanol. Their structures were characterized.
4. Nine novel heterocyclic pentcoordinated organotin(Ⅳ) Schiff base complexes have been synthesized by the reaction of dibenzyltin dichloride, diphenyltin dichloride and di–n–butyltin dichloride with o-aminobenzoic acid Schiff bases in anhydrous methanol. Their structures were characterized.
5. The antibacterial and antitumour activities of the objective compounds 1-12 were determined. The relationships between the bioactivities and the structures of the organotin compounds were also been studied.
引文
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