CN107011259A - 一种抗癌药物5‑氯水杨醛缩‑2‑氯‑6‑肼基吡啶席夫碱锌配合物及合成方法 - Google Patents

一种抗癌药物5‑氯水杨醛缩‑2‑氯‑6‑肼基吡啶席夫碱锌配合物及合成方法 Download PDF

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CN107011259A
CN107011259A CN201710234186.0A CN201710234186A CN107011259A CN 107011259 A CN107011259 A CN 107011259A CN 201710234186 A CN201710234186 A CN 201710234186A CN 107011259 A CN107011259 A CN 107011259A
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chloro
cphp
hcphp
dissolved
chlorine
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张淑华
张少南
陈雅婷
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Guilin University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

一种抗癌药物5‑氯水杨醛缩‑2‑氯‑6‑肼基吡啶席夫碱锌配合物Zn(cphp)2及合成方法。该锌配合物Zn(cphp)2的分子式为：C24H16Cl4N6O2Zn，分子量为：627.60g/mol,Hcphp为5‑氯水杨醛缩‑2‑氯‑6‑肼基吡啶席夫碱。将1.565g分析纯的5‑氯水杨醛，1.436g分析纯的2‑氯‑6‑肼基吡啶，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体Hcphp。将干燥后的0.134‑0.269g Hcphp溶于5‑10mL分析纯DMF，0.145‑0.298g分析纯六水合硝酸锌溶于5‑10mL分析纯乙醇中，置于反应釜中，在80℃烘箱中静置三天，有黄色条状晶体生成即Zn(cphp)2。Zn(cphp)2对癌细胞株均有一定的抑制效果，但对HL‑7702正常肝细胞株细胞对毒性远低于顺铂，是一种无机抗癌药物。本发明工艺简单、成本低廉、化学组分易于控制、重复性好且产量高。

Description

一种抗癌药物5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱锌配合 物及合成方法
技术领域
本发明涉及一种5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱锌配合物Zn(cphp)2(cphp为5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱)及合成方法。
背景技术
水杨醛衍生物席夫碱具有较强的配位能力，能与金属络合，而且具有一定优良的抗肿瘤活性、能够跟生物体细胞中的金属离子形成稳定的有优良药理活性的配合物。在组装和构筑金属有机骨架材料方面有很好的应用前景，是当今社会发展中的一种新型多功能材料。
发明内容
本发明的目的就是为设计合成新型的水杨醛衍生物缩-2-氯-6-肼基吡啶席夫碱锌配合物，利用溶剂热法合成Zn(cphp)2。
本发明涉及的Zn(cphp)2的分子式为：C24H16Cl4N6O2Zn，分子量为：627.60g/mol,Hcphp为5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱，具有良好的生物活性。晶体结构数据见表一,键长键角数据见表二，对部分癌细胞的IC50值见表三。
表一Zn(cphp)2的晶体学参数
表二Zn(cphp)2的部分键长和键角(°)
表三：配合物Zn(cphp)2对不同细胞株的IC50值
表中：MGC803为人胃癌细胞，HepG2为人肝癌细胞，NCI-H460为人乳腺癌细胞，BEL-7404为人卵巢癌细胞，HL-7702为人体正常肝细胞株。
所述Zn(cphp)2的合成方法具体步骤为：
(1)将1.565g分析纯的5-氯水杨醛，1.436g分析纯的2-氯-6-肼基吡啶，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体Hcphp。将干燥后的0.134-0.269g Hcphp溶于5-10mL分析纯DMF，0.1749-0.298g分析纯六水合硝酸锌溶于5-10mL分析纯乙醇中，置于反应釜中，在80℃烘箱中静置三天，有黄色条状晶体生成即Zn(cphp)2。通过单晶衍射仪测定Zn(cphp)2的结构，晶体结构数据见表一,键长键角数据见表二。
本发明具有工艺简单、成本低廉、化学组分易于控制、重复性好并产量高等优点。
附图说明
图1为本发明Zn(cphp)2所用席夫碱配体的结构示意图。
图2为本发明Zn(cphp)2的结构示意图。
具体实施方式
实施例1：
本发明涉及的Zn(cphp)2的分子式为：C24H16Cl4N6O2Zn，分子量为：627.60g/mol,Hcphp为5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱。晶体结构数据见表一,键长键角数据见表二。
Zn(cphp)2的合成方法具体步骤为：
(1)将1.565g分析纯的5-氯水杨醛，1.436g分析纯的2-氯-6-肼基-吡啶，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体Hcphp。
(2)将干燥后的0.134g Hcphp溶于5mL分析纯DMF，0.149g分析纯六水合硝酸锌溶于5mL分析纯乙醇中，置于反应釜中，在80℃烘箱中静置三天，有黄色条状晶体生成即Zn(cphp)2。产量0.088g，产率56％。通过单晶衍射仪测定Zn(cphp)2的结构，晶体结构数据见表一,键长键角数据见表二。
实施例2：
本发明涉及的Zn(cphp)2的分子式为：C24H16Cl4N6O2Zn，分子量为：627.60g/mol,Hcphp为5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱。晶体结构数据见表一,键长键角数据见表二。
Zn(cphp)2的合成方法具体步骤为：
(1)将1.565g分析纯的5-氯水杨醛，1.436g分析纯的2-氯-6-肼基吡啶，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体Hcphp。
(2)将干燥后的0.269g Hcphp溶于10mL分析纯DMF中，0.298g分析纯六水合硝酸锌溶于10mL分析纯乙醇中，置于反应釜中，在80℃烘箱中静置三天，有黄色条状晶体生成即Zn(cphp)2。产量0.182g，产率58％。通过单晶衍射仪测定Zn(cphp)2的结构，晶体结构数据见表一,键长键角数据见表二。

Claims (1)

1.一种抗癌药物5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱锌配合物Zn(cphp)2及合成方法，其特征在于Zn(cphp)2的分子式为：C24H16Cl4N6O2Zn，分子量为：627.60g/mol,Hcphp为5-氯水杨醛缩-2-氯-6-肼基吡啶席夫碱。晶体结构数据见表一,键长键角数据见表二；
所述Zn(cphp)2的合成方法具体步骤为：
(1)将1.565g分析纯的5-氯水杨醛，1.436g分析纯的2-氯-6-肼基吡啶，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体Hcphp。将干燥后的0.134-0.269g Hcphp溶于5-10mL分析纯DMF中，0.149-0.298g分析纯六水合硝酸锌溶于5-10mL分析纯乙醇中，置于反应釜中，在80℃烘箱中静置三天，有红色条状晶体生成即Zn(cphp)2。通过单晶衍射仪测定Zn(cphp)2的结构，晶体结构数据见表一,键长键角数据见表二。
表一 Zn(cphp)2的晶体学参数
表二 Zn(cphp)2的部分键长和键角(°)
CN201710234186.0A 2017-04-11 2017-04-11 一种抗癌药物5‑氯水杨醛缩‑2‑氯‑6‑肼基吡啶席夫碱锌配合物及合成方法 Withdrawn CN107011259A (zh)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112321617A (zh) * 2020-08-13 2021-02-05 江苏省海洋资源开发研究院(连云港) 一种具有生物活性的双核锌配合物及其制备方法与应用

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112321617A (zh) * 2020-08-13 2021-02-05 江苏省海洋资源开发研究院(连云港) 一种具有生物活性的双核锌配合物及其制备方法与应用

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