CN106588994A - Aryl phthalocyanine and ruthenium complexes preparation and use - Google Patents
Aryl phthalocyanine and ruthenium complexes preparation and use Download PDFInfo
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- CN106588994A CN106588994A CN201610947733.5A CN201610947733A CN106588994A CN 106588994 A CN106588994 A CN 106588994A CN 201610947733 A CN201610947733 A CN 201610947733A CN 106588994 A CN106588994 A CN 106588994A
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- phthalocyanine
- ether
- pyridines
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- ruthenium
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 Aryl phthalocyanine Chemical compound 0.000 title description 10
- 150000003303 ruthenium Chemical class 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000012327 Ruthenium complex Substances 0.000 claims abstract description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 12
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims abstract description 11
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 6
- 229910009112 xH2O Inorganic materials 0.000 claims abstract description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims abstract description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 229910019891 RuCl3 Inorganic materials 0.000 claims abstract description 3
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims abstract description 3
- 150000003222 pyridines Chemical class 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 10
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims description 10
- WWRCMNKATXZARA-UHFFFAOYSA-N 1-Isopropyl-2-methylbenzene Chemical compound CC(C)C1=CC=CC=C1C WWRCMNKATXZARA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 229960004756 ethanol Drugs 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- 238000003756 stirring Methods 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 229930007927 cymene Natural products 0.000 abstract 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 abstract 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 2
- QMPSUPWBJMOGPS-UHFFFAOYSA-N [Ru].CC(C)C1=CC=C(C)C=C1 Chemical compound [Ru].CC(C)C1=CC=C(C)C=C1 QMPSUPWBJMOGPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 238000004519 manufacturing process 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
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 208000007578 phototoxic dermatitis Diseases 0.000 description 2
- 231100000018 phototoxicity Toxicity 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 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
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XILYOLONIFWGMT-UHFFFAOYSA-N benzene;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC=C1 XILYOLONIFWGMT-UHFFFAOYSA-N 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 230000007547 defect 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
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000001379 nervous effect Effects 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000375 suspending agent Substances 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
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a phthalocyanine aryl ruthenium complex, which is monochloro-Beta-phthalocyanine 2- (2- Dipyridyl) ether monomethyl isopropylbenzene ruthenium (II). The preparation method of phthalocyanine aryl ruthenium complex includes: 1) dissolving RuCl3 - xH2O and Gamma- Oakene in anhydrous ethanol, heating and stirring under reflux to precipitate to obtain dichloro dichloride cymene diruthenium (II); 2) a-bromo take Beta phthalocyanine, 2 (6 (pyridin-2 dithionite--) is dissolved in ethanol, and the reaction of potassium carbonate in DMF under nitrogen atmosphere,--phthalocyanine precipitated is allowed to stand to give Beta 2 (6 (pyridin-2 dithionite) ether;-- 3)---- the phthalocyanine Beta 2 (6 (pyridin-2 dithionite) and diethyl ether dichlorobis---- (II) are dissolved in anhydrous ethanol, heated and stirred to reflux. After completion of the reaction, the solution is evaporated to remove 2 ml of liquid. 30 ml of n-hexane is added to precipitate red crystals, which is monochloro-beta - phthalocyanine- 2- (6- (2- dithionite pyridine) ether a cymene ruthenium (II). The use of phthalocyanine aryl ruthenium is also disclosed.
Description
Technical field
The invention belongs to technical field of pharmaceuticals, is related to a kind of phthalocyanine aryl ruthenium complex and its production and use, it is special
It is not related to a kind of one β of chlorine-phthalocyanine -5- phenanthrolene ether monomethyls cumene and closes ruthenium (II) and preparation method and purposes.
Background technology
At present, cisplatin has become be used in the world one of most commonly used 3 kinds of medicines for the treatment of cancer, and the year in the U.S. sells
Volume reaches nearly 500,000,000 dollars.But the use of cisplatin there is also certain deficiency, it does not have inhibitory action to some tumors, and easily
Cross resistance is produced with other platinum preparations.Additionally, cisplatin has various side effect, such as nephrotoxicity, peripheral nervouss toxicity, bone marrow poison
Property, haematics toxicity and emetic etc..Therefore, efficient, low toxicity and the new type antineoplastic medicine without cross resistance one are found
It is directly the study hotspot of researcher.
Aryl ruthenium complex is low due to its toxicity, is paid close attention to the characteristics of anti-tumor activity is high and by people.Porphyrin
Compound stablizes nontoxic property due to it, and its good luminescent properties and attract people's attention.With porphyrinses aryl ruthenium
Complex-bound obtains porphyrin and connects aryl ruthenium ruthenium compound, due to aryl ruthenium and the synergism of porphyrin compound, can make it
Possesses phototoxicity on the basis of possessing good anti-tumor activity, reaching strengthens the effect of its cell inhibitory activity.
The content of the invention
It is an object of the invention to solve at least the above and/or defect, and provide at least will be described later excellent
Point.
The present invention separately has a purpose to be to provide a kind of phthalocyanine aryl ruthenium complex.
A further object of the present invention is to provide a kind of preparation method of phthalocyanine aryl ruthenium complex.
It is a still further object of the present invention to provide the purposes of described phthalocyanine aryl ruthenium complex.
For this purpose, the technical scheme that the present invention is provided is：
A kind of phthalocyanine aryl ruthenium complex, the chemical name of the phthalocyanine aryl ruthenium complex is one β of chlorine-phthalocyanine -2-
(6- (2- connects two pyridines) ether monomethyl cumene closes ruthenium (II), and structural formula is as follows：
The preparation method of described phthalocyanine aryl ruthenium complex, comprises the steps：
1) by RuCl that ruthenium weight content is 37%3·xH2O and purity are that 95% γ-terpinene is dissolved in dehydrated alcohol
In, stirring is heated to reflux, stand precipitation and obtain dichloride-two-cymol two rutheniums of conjunction (II)；
2) (6- (2- connects two pyridines) ethanol and potassium carbonate are dissolved in DMF solution, nitrogen protection lower 80 to take the bromo- phthalocyanines of β-, 2-
DEG C reaction after, stand precipitation obtain β-phthalocyanine -2- (6- (2- connects two pyridines) ether；
3) by β-phthalocyanine -2-, (6- (2- connects two pyridines) ether and dichloride-two-cymol close two rutheniums
(II) dehydrated alcohol is dissolved in, heated and stirred backflow, the surplus 2ml liquid of solution evaporation after the completion of reaction, adds 30ml normal hexane, analysis
Go out red crystals, (6- (2- connects two pyridines) ether monomethyl cumene closes ruthenium (II) to as one β of chlorine-phthalocyanine -2-.
Preferably, in the preparation method of described phthalocyanine-aryl ruthenium compound, step 1) in, each component consumption is：
The RuCl3·xH2O is 0.366g, and the γ-terpinene is 3ml, and the dehydrated alcohol is 10ml；
It is described to be heated to reflux mixing time for 6 hours.
Preferably, in the preparation method of described phthalocyanine-aryl ruthenium compound, step 2) in, each component consumption is：
The bromo- phthalocyanine of the β-is 0.1g, and (6- (2- connects two pyridines) ethanol is 0.06g to the 2-, and the potassium carbonate is 0.20g, described
DMF solution is 10ml；
In nitrogen protection, lower 80 DEG C are reacted 8 hours.
Preferably, in the preparation method of described phthalocyanine-aryl ruthenium compound, step 3) in, each component consumption is：
(6- (2- connects two pyridines) ether is 30mg to the β-phthalocyanine -2-, and the dichloride-two-cymol closes two rutheniums
(II) it is 12mg, the dehydrated alcohol is 8ml；
The heated and stirred return time is 6 hours.
The purposes of described phthalocyanine aryl ruthenium complex, is prepared for treating ovary using the phthalocyanine aryl ruthenium complex
The medicine of cancer.
The present invention at least includes following beneficial effect：
The organometallic ruthenium compound of the present invention can be used to prepare the medicine for the treatment of cancer, can be made into injection, tablet, ball
The form of agent, capsule, suspending agent or Emulsion is used.
The preparation method of organometallic ruthenium compound of the present invention is simple, and raw material is easy to get, the advantage with low cost.
The further advantage of the present invention, target and feature embody part by description below, and part will also be by this
The research of invention and practice and be understood by the person skilled in the art.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, to make those skilled in the art with reference to description
Word can be implemented according to this.
It should be appreciated that it is used herein such as " have ", "comprising" and " including " term do not allot one or many
The presence or addition of individual other elements or its combination.
Embodiment 1
A kind of phthalocyanine aryl ruthenium complex, the chemical name of the phthalocyanine aryl ruthenium complex is one β of chlorine-phthalocyanine -2- (6-
(2- connects two pyridines) ether monomethyl cumene closes ruthenium (II)；
Structural formula：
2) physicochemical property：One one β of chlorine-phthalocyanine -2- (6- (2- connects two pyridines) ether monomethyl cumene closes ruthenium (II),
For red crystals, soluble in water and organic solvent, its hydrogen nuclear magnetic resonance modal data is1H NMR:(ppm,CDCl3) δ=1.28
(6H, d, J=6.1Hz), 2.38 (3H, s), 3.95 (2H, m, J=5.9Hz), 3.15 (1H, m, J=5.9Hz), 4.35 (2H, d,
J=5.9Hz), 6.70-7.90 (22H, m, J=5.8Hz), 8.42-8.60 (4H, m, J=5.7Hz).
Embodiment 2
(6- (2- connects two pyridines) ether monomethyl cumene closes the preparation method of ruthenium (II), bag to one one β of chlorine-phthalocyanine -2-
Include following steps：
1) by RuCl that 0.366g ruthenium weight contents are 37%3·xH2O and 3ml purity is that 95% γ-terpinene is dissolved in
10ml dehydrated alcohol, is heated to reflux stirring 6 hours, stands precipitation and obtains dichloride-two-cymol two rutheniums of conjunction
(II)。
2) the bromo- phthalocyanines of 0.1g β-are weighed, (6- (2- connects two pyridines) ethanol, 0.22g potassium carbonate is dissolved in 10ml to 0.05g 2-
DMF solution, after nitrogen protects lower 80 DEG C of reactions 8 hours, stands precipitation and obtains β-phthalocyanine -2- (6- (2- connects two pyridines) ether.
3) by the β of 30mg-phthalocyanine -2- (6- (2- connects two pyridines) ether and 12mg-two-isopropyl methyls of dichloride
Benzene closes two rutheniums (II) and is dissolved in 8ml dehydrated alcohol, and heated and stirred flows back 6 hours, the surplus 2ml liquid of solution evaporation after the completion of reaction,
30ml normal hexane is added, red crystals, as one β of chlorine of product one-phthalocyanine -2- (6- (2- connects two pyridines) ether monomethyls are separated out
Cumene closes ruthenium (II).
Embodiment 3
Using MTT methods, vitro cytotoxicity measure is carried out.The organometallic ruthenium compound that embodiment 1 is obtained and ovum
Nest cancer A2780 cell strain distinguishes 72 hours action time, as a result as shown in table 1.
Medium effective concentration (IC of the organometallic ruthenium compound of table 1 to tumor cell line50)
| Cell strain | A2780 (lucifuge) | A2780 (illumination) |
| IC50(μmol/mL) | 8.3±1.2 | 1.0±0.1 |
Show that ((2- connects two pyrroles to 6- to one β of the chlorine-phthalocyanine -2- of the present invention by the experiment of tumor cell in vitro inhibitory activity
Pyridine) ether monomethyl cumene close ruthenium (II) compounds on ovarian cancer A2780 cell strain there is significant inhibitory action, and
Under visible light illumination its inhibitory action is remarkably reinforced.
It can be seen from the results above that the organometallic ruthenium compound Jing anticancer experiment in vitro of the present invention shows, the change
Compound has strong anti-tumor activity and preferable cell phototoxicity.The present invention is provided to research and develop new antitumor drug
New thinking.
Module number described herein and treatment scale are the explanations for simplifying the present invention.Phthalocyanine virtue to the present invention
Application, the modifications and variations of base ruthenium complex and its production and use are to one skilled in the art apparent
's.
Although embodiment of the present invention is disclosed as above, it is not restricted to listed in description and embodiment
With, it can be applied to completely various suitable the field of the invention, for those skilled in the art, can be easily
Other modification is realized, therefore under the general concept limited without departing substantially from claim and equivalency range, the present invention is not limited
In specific details and shown here as the embodiment with description.
Claims (6)
1. a kind of phthalocyanine aryl ruthenium complex, it is characterised in that the chemical name of the phthalocyanine aryl ruthenium complex is a chlorine one
(6- (2- connects two pyridines) ether monomethyl cumene closes ruthenium (II) to β-phthalocyanine -2-, and structural formula is as follows：
2. the preparation method of phthalocyanine aryl ruthenium complex as claimed in claim 1, it is characterised in that comprise the steps：
1) by RuCl that ruthenium weight content is 37%3·xH2O and purity are that 95% γ-terpinene is dissolved in dehydrated alcohol, plus
Hot reflux is stirred, and is stood precipitation and is obtained dichloride-two-cymol two rutheniums of conjunction (II)；
2) (6- (2- connects two pyridines) ethanol and potassium carbonate are dissolved in DMF solution, and nitrogen protects lower 80 DEG C instead to take the bromo- phthalocyanines of β-, 2-
Ying Hou, stands precipitation and obtains β-phthalocyanine -2- (6- (2- connects two pyridines) ether；
3) by β-phthalocyanine -2-, (it is molten that 6- (2- connects two pyridines) ether and dichloride-two-cymol close two rutheniums (II)
In dehydrated alcohol, heated and stirred backflow, the surplus 2ml liquid of solution evaporation after the completion of reaction, 30ml normal hexane is added, separated out red
(6- (2- connects two pyridines) ether monomethyl cumene closes ruthenium (II) for crystal, as one β of chlorine-phthalocyanine -2-.
3. the preparation method of phthalocyanine as claimed in claim 2-aryl ruthenium compound, it is characterised in that step 1) in, each group
Point consumption is：The RuCl3·xH2O is 0.366g, and the γ-terpinene is 3ml, and the dehydrated alcohol is 10ml；
It is described to be heated to reflux mixing time for 6 hours.
4. the preparation method of phthalocyanine as claimed in claim 2-aryl ruthenium compound, it is characterised in that step 2) in, each group
Point consumption is：The bromo- phthalocyanine of the β-is 0.1g, and (6- (2- connects two pyridines) ethanol is 0.06g to the 2-, and the potassium carbonate is
0.20g, the DMF solution is 10ml；
In nitrogen protection, lower 80 DEG C are reacted 8 hours.
5. the preparation method of phthalocyanine as claimed in claim 2-aryl ruthenium compound, it is characterised in that step 3) in, each group
Point consumption is：The β-phthalocyanine -2- (6- (2- connects two pyridines) ether be 30mg, the dichloride-two-isopropyl methyl
It is 12mg that benzene closes two rutheniums (II), and the dehydrated alcohol is 8ml；
The heated and stirred return time is 6 hours.
6. the purposes of the phthalocyanine aryl ruthenium complex described in claim 1, it is characterised in that coordinated using the phthalocyanine aryl ruthenium
Thing prepares the medicine for treating ovarian cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610947733.5A CN106588994B (en) | 2016-10-26 | 2016-10-26 | Phthalocyanine aryl ruthenium complex and its preparation method and application |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610947733.5A CN106588994B (en) | 2016-10-26 | 2016-10-26 | Phthalocyanine aryl ruthenium complex and its preparation method and application |
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| Publication Number | Publication Date |
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| CN106588994A true CN106588994A (en) | 2017-04-26 |
| CN106588994B CN106588994B (en) | 2019-02-22 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
| CN101851256A (en) * | 2010-04-30 | 2010-10-06 | 广东药学院 | Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof |
-
2016
- 2016-10-26 CN CN201610947733.5A patent/CN106588994B/en 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 (en) * | 2010-04-30 | 2010-10-06 | 广东药学院 | Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| FABIO ZOBI ET AL: "Tagging (Arene)ruthenium(II) Anticancer Complexes with Fluorescent Labels", 《EUR. J. INORG. CHEM.》 * |
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