CN107827914A - 一种铜席夫碱配合物及其制备方法和应用 - Google Patents
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Abstract
本发明涉及一种铜席夫碱配合物及其制备方法和应用,目的是解决现有的铜席夫碱配合物制备方法中存在的操作繁琐、反应时间长、产率低以及存在安全隐患的技术问题,本发明的一种铜席夫碱配合物,其分子式为[Cu2(HL)2(OAc)2]n,其中HL为肼基‑(2‑吡啶基)水杨醛亚胺;本发明铜席夫碱配合物的制备方法,将摩尔比为1:2:2的Cu(OAc)2·H2O、2‑肼基吡啶和水杨醛,加入含有甲醇的聚四氟乙烯管中,所述Cu(OAc)2·H2O与甲醇的摩尔体积比为0.1:(3‑5)mmol/ml;在80‑100℃下反应48‑72h,自然降温,析出黑色棒状晶体,用甲醇溶液洗涤后干燥,即制得所述铜席夫碱配合物。本发明的铜配合物对大肠杆菌、金黄色葡萄球菌及枯草芽孢杆菌具有强的抑菌作用,在生物活性领域有优良的潜在应用前景,可作为新型抗菌剂。
Description
技术领域
本发明涉及一种铜席夫碱配合物及其制备方法和应用。
背景技术
过渡金属配合物由于具有光、电、磁等多种特性,在催化、发光、生物医药等领域表现出广阔的应用前景。现代医学研究表明,铜配合物能够产生抗菌、抗病毒、抗炎、抗肿瘤、酶抑制或化学核酸酶等活性作用,受到越来越多的关注。席夫碱作为一类常见有机化合物,由于其制备简单、结构多样,可以与很多金属离子配位形成稳定的配合物,因此,席夫碱是合成过渡金属配合物的理想配体。同时,席夫碱化合物大多具有抗肿瘤、抗菌等生物活性,在生化反应中起到转氨基作用,碳氮双键是该类化合物具有抗菌活性的效应基团。腙类化合物是一类含有-C=NNH2基团的席夫碱化合物,其结构通常是醛和酮类化合物的氧被-NNH2官能团替代形成,具有特殊的生物活性和强配位能力,它形成配合物后由于协同效应,其生物活性比配位前明显增强,其配合物有着广泛的生物活性和抗癌活性,如抗菌,抗真菌,抗肿瘤,抗惊厥,抗炎,抗血小板聚集等。
Jan Reedijk等人报道了将CuCl2·2H2O与肼基-(2-吡啶基)水杨醛亚胺(HL)通过常规溶液反应制得配合物[[Cu(HL)Cl](MeOH)]n,具体而言,首先需要合成肼基-(2-吡啶基)水杨醛亚胺,再将亚胺与金属盐在甲醇溶剂中反应得到最终配合物(J.Tang,J.S.Costa,A.Pevec,B.C.Massera,O.Roubeau,I.Mutikainen,U.Turpeinen,P.Gamez,J.Reedijk,Cryst.Growth Des.2008,8,1005-1012.)。在此过程中存在着以下问题:1.反应分布进行需要进行多步的产物分离;2.分布反应造成总产率降低;3.反应总时间长;4.反应中将甲醇直接挥发扩散至空气中,存在一定的安全隐患。
发明内容
本发明的目的是解决现有的铜席夫碱配合物制备方法中存在的操作繁琐、反应时间长、产率低以及存在安全隐患的技术问题,提供一种可以作为抑菌剂的铜席夫碱配合物及其制备方法和应用。
本发明所采用的技术方案是:一种铜席夫碱配合物,所述配合物的分子式为[Cu2(HL)2(OAc)2]n,其中HL为肼基-(2-吡啶基)水杨醛亚胺,n代表重复单元数,所述配合物的结构式为:
进一步地,所述配合物的晶体属单斜晶系,空间群为C2/c,晶胞参数为: α=90o,β=120.7(6)o,γ=90o。
上述铜席夫碱配合物的制备方法,包括如下步骤:
(1)将摩尔比为1:2:2的Cu(OAc)2·H2O、2-肼基吡啶和水杨醛,加入含有甲醇的聚四氟乙烯管中,所述Cu(OAc)2·H2O与甲醇的摩尔体积比为0.1:3-5mmol/ml;
(2)将所述聚四氟乙烯管置于不锈钢反应釜中密封,在80-100℃下反应48-72h,自然降温,析出黑色棒状晶体,用甲醇溶液洗涤后干燥,即制得所述铜席夫碱配合物。
进一步地,步骤(2)中反应温度为80℃,反应时间为72h。
上述铜席夫碱配合物用作抑菌剂的应用。
本发明的有益效果是:
1、本发明的铜席夫碱配合物是在溶剂热合成条件下通过一锅反应得到,可以通过简单分离直接获得产物,避免了有机溶剂对空气的污染,制取工艺简单,易操作,周期较短,产率、纯度较高,是一种同时兼顾保护环境和实验效率的有效合成方法。
2、本发明的铜席夫碱配合物是基于腙类水杨醛配体构筑的,对大肠杆菌、金黄色葡萄球菌及枯草芽孢杆菌具有强的抑菌作用,且对大肠杆菌和枯草芽孢杆菌的抑菌活性远远高于光谱抗生素,在生物活性领域有优良的潜在应用前景,可作为新型抗菌剂。
附图说明
图1本发明铜席夫碱配合物的晶体结构图。
具体实施方式
下面结合附图和实施例对本发明进行进一步说明。
实施例1
本实施例中的一种铜席夫碱配合物,所述配合物的分子式为[Cu2(HL)2(OAc)2]n,其中HL为肼基-(2-吡啶基)水杨醛亚胺,n代表重复单元数,所述配合物的结构式为:
所述配合物的晶体属单斜晶系,空间群为C2/c,晶胞参数为: α=90o,β=120.7(6)o,γ=90o。所述配合物的结构基元由2个铜离子、2个肼基-(2-吡啶基)水杨醛亚胺和2个醋酸根组成。中心Cu(Ⅱ)分别与配体HL中的三个原子及两个不同羧酸中的两个O原子配位,构成五配位四棱锥结构。Cu(Ⅱ)与配位原子间的键长分别为:
上述铜席夫碱配合物的制备方法,包括如下步骤:
称取0.1mmol Cu(OAc)2·H2O、0.2mmol 2-肼基吡啶和0.2mmol水杨醛加入含3mL甲醇的聚四氟乙烯管中,将此聚四氟乙烯管密封于不锈钢反应釜中,在80℃下加热72h后,自然降温,析出黑色棒状晶体,用甲醇溶液洗涤后干燥,即制得所述铜席夫碱配合物。
实施例2
本实施例中的一种铜席夫碱配合物与实施例1相同,其制备过程如下:
称取0.1mmolCu(OAc)2·H2O、0.2mmol2-肼基吡啶和0.2mmol水杨醛加入含4mL甲醇的聚四氟乙烯管中,将此聚四氟乙烯管密封于不锈钢反应釜中,在90℃下加热60h后,自然降温,析出黑色棒状晶体,用甲醇溶液洗涤后干燥,即制得所述铜席夫碱配合物。
实施例3
本实施例中的一种铜席夫碱配合物与实施例1相同,其制备过程如下:
称取0.1mmolCu(OAc)2·H2O、0.2mmol2-肼基吡啶和0.2mmol水杨醛加入含5mL甲醇的聚四氟乙烯管中,将此聚四氟乙烯管密封于不锈钢反应釜中,在100℃下加热48h后,自然降温,析出黑色棒状晶体,用甲醇溶液洗涤后干燥,即制得所述铜席夫碱配合物。
对上述实施例所得产物进行元素分析,理论值:C,54.51;H,4.39;N,15.26;实验值:C,54.58;H,4.09;N,15.29。
对所得产物进行铜席夫碱配合物结构测定:采用X-射线单晶衍射,使用经过石墨单色化的Mo-Kα射线扫描方式ω,收集数据的温度为290K。原始数据经SAINT程序还原后,使用SADABS方法进行吸收校正。晶体结构由SHELXL-2014程序直接法解得。晶体结构如图1所示;详细的晶体测定与解析数据见表2;
表2配合物[Cu2(HL)2(OAc)2]n的晶体学数据
对所得产物进行抗菌性测试:
选取革兰氏阴性菌中的大肠杆菌,革兰氏阳性菌中的金黄色葡萄球菌和枯草芽孢杆菌为测试菌,以阿莫西林为对照,采用96孔板法探究了铜席夫碱配合物及阿莫西林对三种细菌的最小抑菌浓度。为了便于观察孔中细菌生长情况,加入INT(碘硝基氯化四氮唑紫)作为细菌染色剂。细菌培养24h后,用肉眼观察,溶液澄清未变色的孔中所含化合物浓度作为此化合物对受试菌的MIC,结果如表1所示。
表1铜席夫碱配合物及对照品对不同细菌的最小抑菌浓度
由表1可知,本发明的铜席夫碱配合物对大肠杆菌、金黄色葡萄球菌及枯草芽孢杆菌具有强的抑菌作用,且对大肠杆菌和枯草芽孢杆菌的抑菌活性远远高于光谱抗生素,在生物活性领域有优良的潜在应用前景,可作为新型抑菌剂。
Claims (5)
1.一种铜席夫碱配合物,其特征在于:所述配合物的分子式为[Cu2(HL)2(OAc)2]n,其中HL为肼基-(2-吡啶基)水杨醛亚胺,n代表重复单元数。所述配合物的结构式为:
2.根据权利要求1所述的一种铜席夫碱配合物,其特征在于:所述配合物的晶体属单斜晶系,空间群为C2/c,晶胞参数为: α=90°,β=120.7(6)°,γ=90°。
3.权利要求1-2所述的一种铜席夫碱配合物的制备方法,其特征在于,包括如下步骤:
(1)将摩尔比为1:2:2的Cu(OAc)2·H2O、2-肼基吡啶和水杨醛,加入含有甲醇的聚四氟乙烯管中,所述Cu(OAc)2·H2O与甲醇的摩尔体积比为0.1:3-5mmol/ml;
(2)将所述聚四氟乙烯管置于不锈钢反应釜中密封,在80-100℃下反应48-72h,自然降温,析出黑色棒状晶体,用甲醇溶液洗涤后干燥,即制得所述铜席夫碱配合物。
4.根据权利要求3所述的铜席夫碱配合物的制备方法,其特征在于:步骤(2)中反应温度为80℃,反应时间为72h。
5.权利要求1-2所述的铜席夫碱配合物用作抑菌剂的应用。
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CN111418558A (zh) * | 2019-09-22 | 2020-07-17 | 山西大学 | 一种消融代谢性泌尿结石动物模型的构建方法 |
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CN110305146A (zh) * | 2019-07-17 | 2019-10-08 | 山西农业大学 | 一种链状席夫碱铜配合物及其制备方法和应用 |
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