二烃基锡酰腙类Schiff碱衍生物的制备、表征与性质研究
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摘要
酰腙Schiff碱因其具有配位能力强、配位形式多样以及生物活性高的特点，在农业、医药、材料、分析试剂等领域得到了广泛应用。有机锡酰腙Schiff碱衍生物结构新颖多样，生物活性优良而成为人们研究的热点课题之一。本文以酰腙类Schiff碱为配体与二烃基锡氧化物或氯化物反应，合成了51个新的二烃基锡衍生物。利用元素分析、红外、核磁、X-射线单晶衍射等技术表征了其结构，解析了11个化合物的晶体结构，测定了代表性化合物的抑菌活性，初步探讨了其构效关系。
1、利用扁桃酰肼、L-焦谷氨酰肼、对硝基芳氧乙酰肼、N,3-二甲基-5-甲硫基-4-吡唑甲酰肼分别和水杨醛、邻羟基苯乙酮、丙酮酸等反应合成了25种酰腙Schiff碱通过用元素分析、核磁、红外确定了其结构，用X-射线单晶衍射测定了和的晶体结构。
2、以上述酰腙Schiff碱为配体，分别与二烃基锡氧化物或氯化物反应，合成了51个新的有机锡衍生物R2SnL。利用元素分析、核磁、红外等手段表征了其结构。测定了和个有机锡衍生物的晶体结构。酰腙Schiff碱以烯醇HO-C=N氧、亚氨氮和羧基氧（或酚羟基氧）与锡原子配位，中心锡原子为五配位的畸变三角双锥构型。晶体中分子或以单体形式存在，或分子之间通过Sn···O等弱相互作用形成二聚体或多聚体结构。
3、利用微量量热法测定五种酰腙Schiff碱化合物和和L221七种有机锡衍生物对大肠杆菌的抑制活性。结果表明合成的12种化合物都有一定的抑菌活性，有机锡衍生物的抑菌效果优于配体，锡上烃基对抑菌活性具有不同的影响，其抑制活性顺序为Bu>Ph>Me。丁基锡的衍生物的抑菌活性优于市售的抗菌药物。本工作为设计合成更高效抗菌药物提供了实验依据。
Acylhydrazone Schiff bases have wildly application in the fields of agriculture, medicine,materials, and analytical reagents because of its unique structural features, strong coordinationability, excellent coordination forms, and high activity of biological drugs. Due to novelstructures and various coordination models, fine biological activity, the derivatives of organotinwith acylhydrazone Schiff base has become a crazy area for researchers. In the thesis,51newdiorganotin derivatives, derived from diorganotin oxides or chlorides and acylhydrazone classSchiff bases, were synthesized and characterized by means of element analysis, IR, NMR, X-raysingle crystal diffraction. The crystal structures of11compounds were resolved. Theantibacterial activities of the typical compounds against Escherichia coli were determined. Therelationship between the structure and activity was discussed preliminarily.
1.25acylhydrazone Schiff bases weresynthesized by the reaction of phenylglycolic hydrazide, L-pyroglutamic hydrazide,p-nitroaryloxyacetyl hydrazide and N,3-dimethyl-5-(methylmercapto)-4-pyrazole-formylhydrazide with salicylic aldehyde, benzoyl acetone, pyroracemic acid, respectively. Theirstructures were characterized by element analysis, IR, NMR, X-ray single crystal diffraction, andthe crystal structures ofere determined.
2.51new derivatives of diorganotin, R2SnL, were synthesized by the reaction of the abovementioned Schiff base with dialkyltin oxides or dialkyltin chorides and characterized by meansof element analysis, IR, NMR, X-ray single crystal diffraction. The crystal structures ofwere measured. The tin atom is penta-coordinated andpossesses a diatorted trigonal bipyramidal geometry. The five coordination atoms come from twocarbon atoms of alkyls, oxygen atom of enolization HO-C=N, oxygen atom of carboxylate (orphenolic hydroxyl group), and the imino nitrogen atom. The molecules of the derivatives exist in monomeric form or dimer or polymeric structure formed by the intermolecular Sn···O weakactions
3. The antibacterial activities of, H2L22and, and against Escherichia coli were determined by using microcalorimetry method.The results show that these compounds all have antibacterial activity. The inhibitory effect oforganotin derivatives is superior to the corresponding ligand, and different substituent-groups onthe tin have different effects, and the order is Bu>Ph> Me. The antibacterial activity of somederivatives is better than that of antimicrobial drugs on the market today. This work provides anexperimental basis for the design and synthesis of more efficient anti-bacterial drugs.
1、利用扁桃酰肼、L-焦谷氨酰肼、对硝基芳氧乙酰肼、N,3-二甲基-5-甲硫基-4-吡唑甲酰肼分别和水杨醛、邻羟基苯乙酮、丙酮酸等反应合成了25种酰腙Schiff碱通过用元素分析、核磁、红外确定了其结构，用X-射线单晶衍射测定了和的晶体结构。
2、以上述酰腙Schiff碱为配体，分别与二烃基锡氧化物或氯化物反应，合成了51个新的有机锡衍生物R2SnL。利用元素分析、核磁、红外等手段表征了其结构。测定了和个有机锡衍生物的晶体结构。酰腙Schiff碱以烯醇HO-C=N氧、亚氨氮和羧基氧（或酚羟基氧）与锡原子配位，中心锡原子为五配位的畸变三角双锥构型。晶体中分子或以单体形式存在，或分子之间通过Sn···O等弱相互作用形成二聚体或多聚体结构。
3、利用微量量热法测定五种酰腙Schiff碱化合物和和L221七种有机锡衍生物对大肠杆菌的抑制活性。结果表明合成的12种化合物都有一定的抑菌活性，有机锡衍生物的抑菌效果优于配体，锡上烃基对抑菌活性具有不同的影响，其抑制活性顺序为Bu>Ph>Me。丁基锡的衍生物的抑菌活性优于市售的抗菌药物。本工作为设计合成更高效抗菌药物提供了实验依据。
Acylhydrazone Schiff bases have wildly application in the fields of agriculture, medicine,materials, and analytical reagents because of its unique structural features, strong coordinationability, excellent coordination forms, and high activity of biological drugs. Due to novelstructures and various coordination models, fine biological activity, the derivatives of organotinwith acylhydrazone Schiff base has become a crazy area for researchers. In the thesis,51newdiorganotin derivatives, derived from diorganotin oxides or chlorides and acylhydrazone classSchiff bases, were synthesized and characterized by means of element analysis, IR, NMR, X-raysingle crystal diffraction. The crystal structures of11compounds were resolved. Theantibacterial activities of the typical compounds against Escherichia coli were determined. Therelationship between the structure and activity was discussed preliminarily.
1.25acylhydrazone Schiff bases weresynthesized by the reaction of phenylglycolic hydrazide, L-pyroglutamic hydrazide,p-nitroaryloxyacetyl hydrazide and N,3-dimethyl-5-(methylmercapto)-4-pyrazole-formylhydrazide with salicylic aldehyde, benzoyl acetone, pyroracemic acid, respectively. Theirstructures were characterized by element analysis, IR, NMR, X-ray single crystal diffraction, andthe crystal structures ofere determined.
2.51new derivatives of diorganotin, R2SnL, were synthesized by the reaction of the abovementioned Schiff base with dialkyltin oxides or dialkyltin chorides and characterized by meansof element analysis, IR, NMR, X-ray single crystal diffraction. The crystal structures ofwere measured. The tin atom is penta-coordinated andpossesses a diatorted trigonal bipyramidal geometry. The five coordination atoms come from twocarbon atoms of alkyls, oxygen atom of enolization HO-C=N, oxygen atom of carboxylate (orphenolic hydroxyl group), and the imino nitrogen atom. The molecules of the derivatives exist in monomeric form or dimer or polymeric structure formed by the intermolecular Sn···O weakactions
3. The antibacterial activities of, H2L22and, and against Escherichia coli were determined by using microcalorimetry method.The results show that these compounds all have antibacterial activity. The inhibitory effect oforganotin derivatives is superior to the corresponding ligand, and different substituent-groups onthe tin have different effects, and the order is Bu>Ph> Me. The antibacterial activity of somederivatives is better than that of antimicrobial drugs on the market today. This work provides anexperimental basis for the design and synthesis of more efficient anti-bacterial drugs.
引文
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