CN106674286B - 四苯基卟啉乙醚芳基钌化合物及制备方法和用途 - Google Patents
四苯基卟啉乙醚芳基钌化合物及制备方法和用途 Download PDFInfo
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
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Abstract
本发明公开了一种四苯基卟啉乙醚芳基钌化合物及制备方法和用途。本发明的卟啉‑芳基钌化合物可用于制备治疗癌症的药物，可制成注射剂、片剂、丸剂、胶囊剂、悬浮剂或乳剂的形式使用。本发明卟啉‑芳基钌化合物的制备方法简单，原料易得，具有成本低的优势。
Description
技术领域
本发明涉及一种四苯基卟啉-2-(6-(2-连二吡啶)乙醚芳基钌化合物及制备方法和用途，尤其涉及一种一氯一四苯基卟啉-2-(6-(2-连二吡啶)乙醚一甲基异丙基苯合钌(II)及制备方法和用途。
背景技术
目前，顺铂已成为世界上用于治疗癌症最为广泛的3种药物之一，在美国的年销售额达到近5亿美元。但顺铂的使用也存在有一定的不足，它对某些肿瘤没有抑制作用，且易与其他铂制剂产生交叉耐药性。此外，顺铂有多种副作用，如肾毒性、外周神经毒性、骨髓毒性、血液学毒性以及催吐性等。因此，寻找高效、低毒且无交叉耐药性的新型抗肿瘤药物一直是科研工作者的研究热点。
芳基钌配合物由于其毒性低，抗肿瘤活性高的特点而受到人们的关注。卟啉类化合物由于其稳定无毒的性质，以及其良好的发光性能而令人瞩目。以卟啉类化合物芳基钌配合物结合得到卟啉连芳基钌钌化合物，由于芳基钌与卟啉化合物的协同作用，能够使其在具备良好抗肿瘤活性的基础上具备光毒性，达到增强其细胞抑制活性的效果。
发明内容
针对上述技术问题，本发明提供了一种四苯基卟啉乙醚芳基钌化合物，可用于制备治疗癌症的药物，且方法简单，原料易得，成本低。
本发明的另一个目的是提供一种四苯基卟啉乙醚芳基钌化合物的制备方法，方法简单，原料易得，成本低。
本发明的又一个目的是提供一种四苯基卟啉乙醚芳基钌化合物的用途。
本发明提供的技术方案为：
一种四苯基卟啉乙醚芳基钌化合物，为一氯一四苯基卟啉-2-(2-二乙胺)乙醚一甲基异丙基苯合钌(II)，其结构式为：
优选的是，所述的四苯基卟啉乙醚芳基钌化合物的制备方法，包括：
1)将0.366g钌重量含量为37％的RuCl3·xH2O和3ml纯度为95％的γ-松油烯溶于10ml无水乙醇，加热回流搅拌6小时，静置析出得到二氯化二氯-二-甲基异丙基苯合二钌(II)；
2)称取0.2g一羟基-四苯基卟啉,0.12g 2-(2-二乙胺)乙醇,溶于10ml DMF溶液，氮气保护下80℃反应6小时后，静置析出得到四苯基卟啉-2-(2-二乙胺)乙醚；
3)将20mg的四苯基卟啉-2-(2-二乙胺)乙醚和12mg二氯化二氯-二-甲基异丙基苯合二钌(II)溶于8ml无水乙醇，加热搅拌回流6小时，反应完成后把溶液蒸发剩2ml液体，加入30ml正己烷，析出红色晶体，即为产物一氯一四苯基卟啉-2-(2-二乙胺)乙醚一甲基异丙基苯合钌(II)。
优选的是，所述的四苯基卟啉乙醚芳基钌化合物的用途中，利用所述四苯基卟啉乙醚芳基钌化合物制备用于治疗卵巢癌的药物。
本发明具有以下有益效果：
1、本发明的卟啉-芳基钌化合物可用于制备治疗癌症的药物，可制成注射剂、片剂、丸剂、胶囊剂、悬浮剂或乳剂的形式使用。
2、本发明卟啉-芳基钌化合物的制备方法简单，原料易得，具有成本低的优势。
具体实施方式
下面对本发明做进一步的详细说明，以令本领域技术人员参照说明书文字能够据以实施。
实施例一
一种四苯基卟啉乙醚芳基钌化合物，为一氯一四苯基卟啉-2-(2-二乙胺)乙醚一甲基异丙基苯合钌(II)，其结构式为：
一氯一四苯基卟啉-2-(2-二乙胺)乙醚一甲基异丙基苯合钌(II)的理化性质为：为红色晶体，易溶于水和有机溶剂，其核磁共振氢谱数据为1H NMR:(ppm,CDCl3)δ＝1.30(6H,d,J＝6.1Hz),2.35(3H,s),3.13(1H,m,J＝6.2Hz),2.70-4.10(8H,m,J＝5.8Hz),5.20-6.50(8H,m,J＝5.8Hz),6.70-7.20(23H,m,J＝6.0Hz)。
实施例二
实施例一所述的四苯基卟啉乙醚芳基钌化合物的制备方法包括：
1)将0.366g钌重量含量为37％的RuCl3·xH2O和3ml纯度为95％的γ-松油烯溶于10ml无水乙醇，加热回流搅拌6小时，静置析出得到二氯化二氯-二-甲基异丙基苯合二钌(II)。
2)称取0.2g一羟基-四苯基卟啉,0.12g 2-(2-二乙胺)乙醇,溶于10ml DMF溶液，氮气保护下80℃反应6小时后，静置析出得到四苯基卟啉-2-(2-二乙胺)乙醚。
3)将20mg的四苯基卟啉-2-(2-二乙胺)乙醚和12mg二氯化二氯-二-甲基异丙基苯合二钌(II)溶于8ml无水乙醇，加热搅拌回流6小时，反应完成后把溶液蒸发剩2ml液体，加入30ml正己烷，析出红色晶体，即为产物一氯一四苯基卟啉-2-(2-二乙胺)乙醚一甲基异丙基苯合钌(II)。
实施例三
采用实施例一制备得到四苯基卟啉乙醚芳基钌化合物进行体外抗肿瘤活性实验：
采用MTT方法，进行体外细胞毒性测定。将实施例1得到的四苯基卟啉乙醚芳基钌化合物与胃癌SGC 7901细胞株分别作用时间72小时，结果如表1所示。
表1四苯基卟啉乙醚芳基钌化合物对肿瘤细胞株的半数有效浓度(IC50)
从表1的结果可以看出，本发明的四苯基卟啉乙醚芳基钌化合物经体外抗肿瘤实验表明，该化合物具有强的抗肿瘤活性以及较好的细胞光毒性。
尽管本发明的实施方案已公开如上，但其并不仅仅限于说明书和实施方式中所列运用，它完全可以被适用于各种适合本发明的领域，对于熟悉本领域的人员而言，可容易地实现另外的修改，因此在不背离权利要求及等同范围所限定的一般概念下，本发明并不限于特定的细节。
Claims (3)
1.一种四苯基卟啉乙醚芳基钌化合物，其特征在于，其结构式如式(I)所示：
2.如权利要求1所述的四苯基卟啉乙醚芳基钌化合物的制备方法，其特征在于，包括：
1)将0.366g钌重量含量为37％的RuCl3·xH2O和3ml纯度为95％的γ-松油烯溶于10ml无水乙醇，加热回流搅拌6小时，静置析出得到式(Ⅱ)所示化合物；
2)称取0.2g一羟基-四苯基卟啉,0.12g羟乙基乙二胺,溶于10ml DMF溶液，氮气保护下80℃反应6小时后，静置析出得到式(III)所示化合物；
3)将20mg的式(Ⅲ)所示化合物和12mg式(Ⅱ)所示化合物溶于8ml无水乙醇，加热搅拌回流6小时，反应完成后把溶液蒸发剩2ml液体，加入30ml正己烷，析出红色晶体，即为产物。
3.如权利要求1所述的四苯基卟啉乙醚芳基钌化合物的用途，其特征在于，利用所述四苯基卟啉乙醚芳基钌化合物制备用于治疗卵巢癌的药物。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102015743A (zh) * | 2008-02-08 | 2011-04-13 | 本尤明·A·科恩 | 钌化合物和组合物 |
| CN103239718A (zh) * | 2013-05-13 | 2013-08-14 | 江苏大学 | 负载阿霉素的聚己内酯-嵌段-聚乙二醇纳米微球的制备方法 |
| CN103298804A (zh) * | 2009-04-29 | 2013-09-11 | 多异亚德韩国株式会社 | 新的二氢卟酚e6-叶酸共轭物、其制备方法以及含有该共轭物的用于癌症治疗的药物组合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102015743A (zh) * | 2008-02-08 | 2011-04-13 | 本尤明·A·科恩 | 钌化合物和组合物 |
| CN103298804A (zh) * | 2009-04-29 | 2013-09-11 | 多异亚德韩国株式会社 | 新的二氢卟酚e6-叶酸共轭物、其制备方法以及含有该共轭物的用于癌症治疗的药物组合物 |
| CN103239718A (zh) * | 2013-05-13 | 2013-08-14 | 江苏大学 | 负载阿霉素的聚己内酯-嵌段-聚乙二醇纳米微球的制备方法 |
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