CN103613528A - 两种具有抗菌活性吡咯酰腙铜配合物的合成 - Google Patents
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Abstract
本发明涉及两种具有抗菌活性吡咯酰腙铜配合物的合成，属于配合物合成技术领域。其中(1)配体HL合成采用无水乙醇、2-乙氧羰基-3、4-二甲基-5-甲酰基吡咯和对羟基苯甲酰肼加入到圆底烧瓶中，回流搅拌，冷却后有HL生成，抽滤后，N，N-二甲基甲酰胺重结晶形成HL·DMF。(2)配合物1和2的合成取配体HL溶于甲醇和四氢呋喃的混合溶液中，加入醋酸铜，轻微搅拌使其溶解，常温下静置，出现棕色块状晶体1。将氯化铜替代醋酸铜，溶剂换为DMF，同样方法合成绿色块状晶体2。上述方法合成的吡咯酰腙铜配合物方法简单，制备所得到的配合物具有较好的抗菌活性，适合于在抗菌制药、化工领域使用。
Description
技术领域
本发明涉及两种具有抗菌活性吡咯酰腙铜配合物的合成，属于配合物合成技术领域。
背景技术
多年的研究发现，一些吡咯酰腙具有良好的杀菌抗癌作用。而其配合物因具有更强的脂溶性和细胞穿透性，所以它的抗菌谱更广，且不易产生耐药性，拥有更好的医药价值。近来研究发现人体的微量元素，特别是某些金属元素的缺乏或过量，可能严重地降低人体对致癌因子的抵抗能力。另外，元素之间的拮抗作用，元素与其它致癌因素之间的综合效应，都可能与癌症的发生有密切的关系。由于金属元素在人体内起着重要的药理和生理作用，以及1969年发现了顺铂具有抗癌活性，从而使人们对金属配合物抗癌药物寄予特别的希望。
发明内容
本发明的目的在于提供两种具有抗菌活性吡咯酰腙铜配合物的合成，并对其进行测定，以提供具有抗菌活性配合物合成方法。
为了实现上述目的，本发明的技术方案如下。两种具有抗菌活性吡咯酰腙铜配合物的合成，包括配体HL的合成和配合物1和2的合成，其中：
(1)配体HL的合成步骤为：无水乙醇10ml，2-乙氧羰基-3，4-二甲基-5-甲酰基吡咯1.0mmol和对羟基苯甲酰肼1.0mmol加入到50ml的圆底烧瓶中，在75℃下回流搅拌3h，冷却后有淡黄色固体生成，(HL)。抽滤，N，N-二甲基甲酰胺(DMF)重结晶得(HL·DMF)。
HL的产率为76％，熔点92～94℃。检测数据为：IR(cm-1)：vNH：3282；vC=O(ester)：1677；vC=O(amide)：1650；vC=N：1608。1H NMR(CD3COCD3，400MHz)，δ(ppm)：9.15(H，s，NH-C=O)；8.95(H，s，pyrrole NH)；7.67(H，s，CH=N)；7.12-7.31(4H，m，phenyl H)；6.27(H，s，OH)；4.34-4.39(2H，q，J=7.2Hz，CH2-CH3)；2.26(3H，s，CH3)；2.08(3H，s，CH3)；1.37-1.41(3H，t，J=7.2Hz，CH3-CH2)。
(2)配合物1和2的合成步骤为：取1mmo配体HL溶于甲醇和四氢呋喃的混合溶液中，加入1mmol的醋酸铜，轻微搅拌使其溶解，常温下静置一周，出现棕色块状晶体1。将氯化铜替代醋酸铜，溶剂换为DMF，同样方法合成绿色块状晶体2。
其中，配合物1为棕色块状晶体，产率：76％。检测数据为：IR(KBr)：vNH：3302；vC=O(ester)：1688；vC=N：1610，1594。配合物2为绿色块状晶体，产率：72％。检测数据为：IR(KBr)：vNH：3243；vC=O(DMF)：1695；vC=O(ester)：1685；vC=N：1601，1587。
针对上述配合物，进行的最低抑菌浓度(MIC)测定采用涂平板的方法进行。其具体方法为：在用来培养细菌的营养肉汤基培养基(BPY)、培养霉菌的马铃薯培养基(PDA)和培养酵母菌酵母培养基(YPD)中添加浓度梯度从2到20mg／mL。阳性对照为氨苄青霉素(Amp)，硫酸链霉素(Str)和硫酸卡那霉素(Kan)，阴性对照制霉菌素(Nys)。分别取0.1mL细菌细胞(106CFU／mL)和真菌细胞或孢子(5×105CFU／mL)的标准悬浮培养液接种到平板上，然后把每个稀释浓度的目标化合物和抗生素对照涂布到接种后的平板上，在37℃恒温培养箱中培养细菌24h，28℃恒温培养箱中培养真菌48～96h后观察。以肉眼检测下，菌株没有增殖的最低浓度和菌株没有明显增殖的最高浓度的平板培养的目标化合物的平均值为目标化合物对该菌株的最低抑菌浓度。配合物1和2对金黄色葡萄球菌的最低抑菌浓度达到20～80ug／ml。
该发明的有益效果在于：上述方法合成所制备的吡咯酰腙铜配合物方法简单，充分利用化合物合成方式，简化了工艺要求，同时制备所得到的吡咯酰腙铜配合物具有较好的抗菌活性，适合于在抗菌制药、化工领域使用。
附图说明
图1为该发明实施例中配体HL·DMF的晶体结构图(氢原子省略)。
图2为该发明实施例中配合物1的晶体结构图(氢原子省略)。
图3为该发明实施例中配合物2的晶体结构图(氢原子省略)。
具体实施方式
下面结合实施例进一步阐述该发明的具体实施方式。
实施例1：
配体HL的合成，其具体步骤为：无水乙醇10ml，2-乙氧羰基-3，4-二甲基-5-甲酰基吡咯1.0mmol和对羟基苯甲酰肼1.0mmol加入到50ml的圆底烧瓶中，在75℃下回流搅拌3h，冷却后有淡黄色固体生成，(HL)。抽滤，N，N-二甲基甲酰胺(DMF)重结晶(HL·DMF)。其中HL的产率为76％，熔点92～94℃。检测数据为：IR(cm-1)：vNH：3282；vC=O(ester)：1677；vC=O(amide)：1650；vC=N：1608。1H NMR(CD3COCD3，400MHz)，δ(ppm)：9.15(H，s，NH-C=O)；8.95(H，s，pyrrole NH)；7.67(H，s，CH=N)；7.12-7.31(4H，m，phenyl H)；6.27(H，s，OH)；4.34-4.39(2H，q，J=7.2Hz，CH2-CH3)；2.26(3H，s，CH3)；2.08(3H，s，CH3)；1.37-1.41(3H，t，J=7.2Hz，CH3-CH2)。配体HL·DMF的晶体结构图(氢原子省略)见图1。
实施例2：
配合物1和2的合成，其步骤为：取1mmo配体HL溶于甲醇和四氢呋喃的混合溶液中，加入1mmol的醋酸铜，轻微搅拌使其溶解，常温下静置一周，出现棕色块状晶体1。将氯化铜替代醋酸铜，溶剂换为DMF，同样方法合成绿色块状晶体2。其中，配合物1为棕色块状晶体，产率：76％。检测数据为：IR(KBr)：vNH：3302；vC=O(ester)：1688；vC=N：1610，1594。配合物1的晶体结构图(氢原子省略)见图2。配合物2为绿色块状晶体，产率：72％。检测数据为：IR(KBr)：vNH：3243；vC=O(DMF)：1695；vC=O(ester)：1685；vC=N：1601，1587。配合物2的晶体结构图(氢原子省略)见图3。
实施例3：
针对上述配合物进行最低抑菌浓度(MIC)测定采用涂平板的方法进行。其具体方法为：在用来培养细菌的营养肉汤基培养基(BPY)、培养霉菌的马铃薯培养基(PDA)和培养酵母菌酵母培养基(YPD)中添加浓度梯度从2到20mg／mL。阳性对照为氨苄青霉素(Amp)，硫酸链霉素(Str)和硫酸卡那霉素(Kan)，阴性对照制霉菌素(Nys)。分别取0.1mL细菌细胞(106CFU／mL)和真菌细胞或孢子(5×105CFU／mL)的标准悬浮培养液接种到平板上，然后把每个稀释浓度的目标化合物和抗生素对照涂布到接种后的平板上，在37℃恒温培养箱中培养细菌24h，28℃恒温培养箱中培养真菌48～96h后观察。以肉眼检测下，菌株没有增殖的最低浓度和菌株没有明显增殖的最高浓度的平板培养的目标化合物的平均值为目标化合物对该菌株的最低抑菌浓度。配合物1和2对金黄色葡萄球菌的最低抑菌浓度达到20～80ug／ml。
以上所述是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰也视为本发明的保护范围。
Claims (4)
1.两种具有抗菌活性吡咯酰腙铜配合物的合成，包括配体HL的合成和配合物1和2的合成，其特征在于：
所述配体HL的合成步骤为：无水乙醇10ml、2-乙氧羰基-3、4-二甲基-5-甲酰基吡咯各1.0mmol和对羟基苯甲酰肼1.0mmol加入到50ml的圆底烧瓶中，在75℃下回流搅拌3h，冷却后有淡黄色固体HL生成，抽滤后N，N-二甲基甲酰胺(DMF)重结晶即得到HL·DMF；
所述配合物1和2的合成步骤为：取1mmo配体HL溶于甲醇和四氢呋喃的混合溶液中，加入1mmol的醋酸铜，轻微搅拌使其溶解，常温下静置一周，出现棕色块状晶体1；将氯化铜替代醋酸铜，溶剂换为DMF，同样方法合成绿色块状晶体2。
2.根据权利要求1所述的两种具有抗菌活性吡咯酰腙铜配合物的合成，其特征在于：所制得的HL的产率为76％，熔点92～94℃。
3.根据权利要求1所述的两种具有抗菌活性吡咯酰腙铜配合物的合成，其特征在于：所制得的配合物1为棕色块状晶体，产率：76％；所制得的配合物2为绿色块状晶体，产率：72％。
4.根据权利要求1所述的两种具有抗菌活性吡咯酰腙铜配合物的合成，其特征在于：针对上述配合物，进行最低抑菌浓度(MIC)测定，采用涂平板的方法，其具体方法为：在用来培养细菌的营养肉汤基培养基(BPY)、培养霉菌的马铃薯培养基(PDA)和培养酵母菌酵母培养基(YPD)中添加浓度梯度从2到20mg／mL；阳性对照为氨苄青霉素(Amp)，硫酸链霉素(Str)和硫酸卡那霉素(Kan)，阴性对照制霉菌素(Nys)；分别取0.1mL细菌细胞(106CFU／mL)和真菌细胞或孢子(5×105CFU／mL)的标准悬浮培养液接种到平板上，然后把每个稀释浓度的目标化合物和抗生素对照涂布到接种后的平板上，在37℃恒温培养箱中培养细菌24h，28℃恒温培养箱中培养真菌48～96h后观察；以肉眼检测下，菌株没有增殖的最低浓度和菌株没有明显增殖的最高浓度的平板培养的目标化合物的平均值为目标化合物对该菌株的最低抑菌浓度，采用上述方法测试得到配合物1和2对金黄色葡萄球菌的最低抑菌浓度达到20～80ug／ml。
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| CN103951602B (zh) * | 2014-03-19 | 2016-06-15 | 河南理工大学 | 具有抗肿瘤活性的吡咯缩氨基硫脲铜、镍配合物的合成方法 |
| CN107312180A (zh) * | 2016-10-09 | 2017-11-03 | 河南理工大学 | 一种罕见的含有六重螺旋链的多孔mof的合成方法 |
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