CN106632494A - 卟啉芳基钌配合物及其制备方法和用途 - Google Patents
卟啉芳基钌配合物及其制备方法和用途 Download PDFInfo
- Publication number
- CN106632494A CN106632494A CN201611046004.9A CN201611046004A CN106632494A CN 106632494 A CN106632494 A CN 106632494A CN 201611046004 A CN201611046004 A CN 201611046004A CN 106632494 A CN106632494 A CN 106632494A
- Authority
- CN
- China
- Prior art keywords
- porphyrin
- tetraphenylporphyrin
- pyridines
- connects
- ruthenium complex
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000012327 Ruthenium complex Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- 150000003222 pyridines Chemical class 0.000 claims description 18
- 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 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 235000019441 ethanol Nutrition 0.000 claims description 8
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims description 8
- 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
- -1 porphyrin aryl ruthenium Compound Chemical class 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
- WWRCMNKATXZARA-UHFFFAOYSA-N 1-Isopropyl-2-methylbenzene Chemical compound CC(C)C1=CC=CC=C1C WWRCMNKATXZARA-UHFFFAOYSA-N 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
- 239000007788 liquid 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910009112 xH2O Inorganic materials 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 6
- 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
- 239000000375 suspending agent Substances 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 208000007578 phototoxic dermatitis Diseases 0.000 description 2
- 231100000018 phototoxicity Toxicity 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
- 238000012404 In vitro experiment Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000009286 beneficial 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
- 229940079593 drug Drugs 0.000 description 1
- 239000002895 emetic Substances 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
- 238000000338 in vitro 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
- 150000004032 porphyrins Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201611046004.9A CN106632494B (zh) | 2016-11-22 | 2016-11-22 | 卟啉芳基钌配合物及其制备方法和用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201611046004.9A CN106632494B (zh) | 2016-11-22 | 2016-11-22 | 卟啉芳基钌配合物及其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106632494A true CN106632494A (zh) | 2017-05-10 |
CN106632494B CN106632494B (zh) | 2019-04-26 |
Family
ID=58812444
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201611046004.9A Active CN106632494B (zh) | 2016-11-22 | 2016-11-22 | 卟啉芳基钌配合物及其制备方法和用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106632494B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109867680A (zh) * | 2017-12-01 | 2019-06-11 | 中国科学院大连化学物理研究所 | 一种四吡啶基卟啉锌-八核钌配合物及其制备和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
2016
- 2016-11-22 CN CN201611046004.9A patent/CN106632494B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Non-Patent Citations (1)
Title |
---|
FABIO ZOBI ET AL.: "Tagging (Arene)ruthenium(II) Anticancer Complexes with Fluorescent Labels", 《EUR. J. INORG. CHEM.》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109867680A (zh) * | 2017-12-01 | 2019-06-11 | 中国科学院大连化学物理研究所 | 一种四吡啶基卟啉锌-八核钌配合物及其制备和应用 |
CN109867680B (zh) * | 2017-12-01 | 2021-08-31 | 中国科学院大连化学物理研究所 | 一种四吡啶基卟啉锌-八核钌配合物及其制备和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN106632494B (zh) | 2019-04-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Sirajuddin et al. | Organotin (IV) derivatives based on 2-((2-methoxyphenyl) carbamoyl) benzoic acid: Synthesis, spectroscopic characterization, assessment of antibacterial, DNA interaction, anticancer and antileishmanial potentials | |
CN111072727B (zh) | 基于8-羟基喹啉衍生物和2-苯基吡啶铱二聚体构筑的铱配合物及其合成方法和应用 | |
CN108191918A (zh) | 卤代8-羟基喹啉铂(ii)配合物及其合成方法和应用 | |
CN107955042A (zh) | 具有抗癌活性的铂类配合物、制备方法及应用 | |
Corona-Motolinia et al. | Synthesis, crystal structure, and computational methods of vanadium and copper compounds as potential drugs for cancer treatment | |
CN106632494A (zh) | 卟啉芳基钌配合物及其制备方法和用途 | |
Qi et al. | Synthesis, structure and anticancer studies of Cu (Ⅱ) and Ni (Ⅱ) complexes based on 2-hydroxy-1-naphthaldehyde-4-aminoantipyrine Schiff-base | |
CN102964387B (zh) | 一种有机金属钌离子对化合物及其制备方法和用途 | |
CN108358977A (zh) | 一种双核钌的Schiff碱配合物的制备方法及其应用 | |
CN106749422B (zh) | 四苯基卟啉芳基钌化合物及其制备方法和用途 | |
CN106674286B (zh) | 四苯基卟啉乙醚芳基钌化合物及制备方法和用途 | |
CN106588995B (zh) | 酞菁-芳基钌化合物及其制备方法和用途 | |
CN110423252A (zh) | Krebs型多酸化合物及其制备方法 | |
CN106588939B (zh) | 酞菁-芳基钌化合物及其制备方法和用途 | |
CN108383880A (zh) | 靶向于卵巢癌耐药株的香豆素-铂(ii)配合物及其合成方法与应用 | |
CN106632493B (zh) | 四苯基卟啉连二胺芳基钌化合物及其制备方法和用途 | |
CN102060792B (zh) | 2′-胺基查尔酮唑类化合物及其吡唑啉和环丙基唑类衍生物、制备方法与用途 | |
CN103288881B (zh) | 一种具有抗肿瘤活性的双核金属钌配合物 | |
Yan et al. | Water-soluble ferrocene complexes (WFCs) functionalized silica nanospheres for WFC delivery in HepG2 tumor therapy | |
CN106588994B (zh) | 酞菁芳基钌配合物及其制备方法和用途 | |
CN102964385A (zh) | 一种有机金属钌化合物及其制备方法和用途 | |
CN106588996B (zh) | 酞菁芳基钌配合物及其制备方法和用途 | |
CN104370971A (zh) | 一种氰基乙烯基钌化合物及其制备方法和用途 | |
CN104262409B (zh) | 一种用于治疗肝癌的有机化合物及其制备方法和用途 | |
CN105440085A (zh) | 9-苯并噻蒽腙-钌(ii)配合物及其合成方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CP01 | Change in the name or title of a patent holder |
Address after: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee after: NANNING NORMAL University Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee before: Guangxi Normal University |
|
CP01 | Change in the name or title of a patent holder | ||
TR01 | Transfer of patent right |
Effective date of registration: 20191025 Address after: Jiaxing City, Zhejiang province 314500 Tongxiang Tongxiang City Economic Development Zone high-tech West Road No. 518 Patentee after: HONGGUAN BIO-PHARMA Co.,Ltd. Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee before: Nanning Normal University |
|
TR01 | Transfer of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Porphyrin aryl ruthenium complex and its preparation method and use Effective date of registration: 20220831 Granted publication date: 20190426 Pledgee: Bank of Hangzhou Limited by Share Ltd. Tongxiang branch Pledgor: HONGGUAN BIO-PHARMA Co.,Ltd. Registration number: Y2022330001992 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20190426 Pledgee: Bank of Hangzhou Limited by Share Ltd. Tongxiang branch Pledgor: HONGGUAN BIO-PHARMA Co.,Ltd. Registration number: Y2022330001992 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |