CN106632493A - 四苯基卟啉连二胺芳基钌化合物及其制备方法和用途 - Google Patents
四苯基卟啉连二胺芳基钌化合物及其制备方法和用途 Download PDFInfo
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- -1 5,10,15,20-tetraphenylporphyrin diamine aryl ruthenium compound Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 8
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 claims description 34
- 150000004985 diamines Chemical class 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims description 8
- WWRCMNKATXZARA-UHFFFAOYSA-N 1-Isopropyl-2-methylbenzene Chemical compound CC(C)C1=CC=CC=C1C WWRCMNKATXZARA-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229910009112 xH2O Inorganic materials 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002775 capsule Substances 0.000 abstract description 2
- 239000000839 emulsion Substances 0.000 abstract description 2
- 238000002347 injection Methods 0.000 abstract description 2
- 239000007924 injection Substances 0.000 abstract description 2
- 239000006187 pill Substances 0.000 abstract description 2
- 239000000725 suspension Substances 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 0 **N(CCN)C(c(cc1)ccc1C(c1cc*(C(c2ccccc2)=C(C=C2)N=C2C(c2ccccc2)=C(C=C2)NC2=C(c2ccccc2)C(C=C2)=C)[n]1)=C2N)=O Chemical compound **N(CCN)C(c(cc1)ccc1C(c1cc*(C(c2ccccc2)=C(C=C2)N=C2C(c2ccccc2)=C(C=C2)NC2=C(c2ccccc2)C(C=C2)=C)[n]1)=C2N)=O 0.000 description 2
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 239000012327 Ruthenium complex Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 208000007578 phototoxic dermatitis Diseases 0.000 description 2
- 231100000018 phototoxicity Toxicity 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
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- 210000004881 tumor cell Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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连二胺芳基钌化合物及其制备方法和用途。本发明的所述的四苯基卟啉连二胺芳基钌化合物可用于制备治疗卵巢癌的药物，可制成注射剂、片剂、丸剂、胶囊剂、悬浮剂或乳剂的形式使用。本发明所述的四苯基卟啉连二胺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连二胺芳基钌及制备方法和用途，尤其涉及一氯一四-苯基卟啉连二胺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连二胺芳基钌化合物，可用于制备治疗癌症的药物。
本发明的另一个目的是提供一种四苯基卟啉连二胺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连二胺芳基钌化合物的用途。
本发明提供的技术方案为：
一种四苯基卟啉连二胺芳基钌化合物，为一氯一四-苯基卟啉连二胺一甲基异丙基苯合钌(II)，其结构式为：
优选的是，所述的四苯基卟啉连二胺芳基钌化合物的制备方法中，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0.095g一羧基-四-苯基卟啉,0.12g叔丁基-2-氨基-氨基甲酸乙酯,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-苯基卟啉连二胺。
3)将20mg的四-苯基卟啉连二胺和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-苯基卟啉连二胺一甲基异丙基苯合钌(II)。
优选的是，所述的四苯基卟啉连二胺芳基钌化合物的制备方法中，利用所述四-苯基卟啉连二胺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)本发明的所述的四-苯基卟啉连二胺芳基钌化合物可用于制备治疗卵巢癌的药物，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)本发明所述的四-苯基卟啉连二胺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
本实施例制备一种四-苯基卟啉连二胺芳基钌化合物，为一氯一四-苯基卟啉连二胺一甲基异丙基苯合钌(II)，其结构式为：
一氯一四-苯基卟啉连二胺一甲基异丙基苯合钌(II)的理化性质：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＝6.9Hz),2.35(3H,s),2.95(2H,d,J＝5.9Hz),3.12(1H,m,J＝6.9Hz),3.46(2H,d,J＝5.9Hz),5.30-6.10(8H,m,J＝6.1Hz),7.14-7.90(19H,m,J＝6.1Hz)。
实施例二
实施例一中的四-苯基卟啉连二胺芳基钌化合物的制备方法中，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0.095g一羧基-四-苯基卟啉、0.12g叔丁基-2-氨基-氨基甲酸乙酯，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-苯基卟啉连二胺；
3)将20mg的四-苯基卟啉连二胺和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-苯基卟啉连二胺一甲基异丙基苯合钌(II)。
所述的四-苯基卟啉连二胺芳基钌化合物的制备方法中，利用所述四-苯基卟啉连二胺芳基钌化合物制备用于治疗卵巢癌的药物。
实施例三
采用实施例一制备得到四-苯基卟啉连二胺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。将实施例一得到的四-苯基卟啉连二胺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-苯基卟啉连二胺芳基钌化合物对肿瘤细胞株的半数有效浓度(IC50)
| 细胞株 | A2780(避光) | A2780(光照) |
| IC50(umol/mL) | 8.0±1.5 | 1.2±0.2 |
从表1的结果可以看出，本发明的有机金属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)
1.一种四苯基卟啉连二胺芳基钌化合物，其特征在于，为一氯一四-苯基卟啉连二胺一甲基异丙基苯合钌(II)，其结构式为：
2.如权利要求1所述的四苯基卟啉连二胺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，静置析出得到二氯化二氯-二-甲基异丙基苯合二钌(II)；
2)称取0.095g一羧基-四-苯基卟啉,0.12g叔丁基-2-氨基-氨基甲酸乙酯,溶于10mlDMF溶液，氮气保护下80℃反应6小时后，静置析出得到四-苯基卟啉连二胺。
3)将20mg的四-苯基卟啉连二胺和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-苯基卟啉连二胺一甲基异丙基苯合钌(II)。
3.如权利要求1所述的四苯基卟啉连二胺芳基钌化合物的用途，其特征在于，利用所述四-苯基卟啉连二胺芳基钌化合物制备用于治疗卵巢癌的药物。
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| WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
| CN101851256A (zh) * | 2010-04-30 | 2010-10-06 | 广东药学院 | 一种以柔性碳链联接的钌(ⅱ)卟啉配合物及其制备方法和应用 |
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| WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
| CN101851256A (zh) * | 2010-04-30 | 2010-10-06 | 广东药学院 | 一种以柔性碳链联接的钌(ⅱ)卟啉配合物及其制备方法和应用 |
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| Title |
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| FABIO ZOBI ET AL.: "Tagging (Arene)ruthenium(II) Anticancer Complexes with Fluorescent Labels", 《EUR. J. INORG. CHEM.》 * |
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