CN106432185A - Complex [Co(L1)2(H2O)] and application thereof in preparation of anticancer drugs - Google Patents
Complex [Co(L1)2(H2O)] and application thereof in preparation of anticancer drugs Download PDFInfo
- Publication number
- CN106432185A CN106432185A CN201610818040.6A CN201610818040A CN106432185A CN 106432185 A CN106432185 A CN 106432185A CN 201610818040 A CN201610818040 A CN 201610818040A CN 106432185 A CN106432185 A CN 106432185A
- Authority
- CN
- China
- Prior art keywords
- complex
- room temperature
- pyridine
- pure
- hydroxyl
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses complex [Co(L1)2(H2O)] and application thereof in the preparation of anticancer drugs. A molecular formula of [Co(L1)2(H2O)] is C20H18CoN6O7, with a molecular weight of 513.33 and good bioactivity. The complex is synthesized by: (1) dissolving 0.05-0.15 g of analytically pure methyl 1-(2-pyridine)-5-hydroxyl-1H-pyrazole-3-carboxylate and 0.05-0.15 g of analytically pure cobalt acetate dihydrate in 15-20 ml of a mixed solution of anhydrous acetonitrile and analytically pure ethanol having a volume ratio of 8:2; (2) transferring to a polytetrafluoroethylene reactor, reacting at 80-90 DEG C for 60-80 h, cooling to room temperature, filtering, and naturally volatilizing and crystallizing at room temperature. [Co(L1)2(H2O)] is equivalent to cis-platinum in IC50 value for HepG2 cancer cell line and MGC80-3 cancer cell line, but far lower than cis-platinum in toxicity for HL-7702 normal hepatic cell line cells. The defects of solvent method are overcome, the process is simple and low in cost, chemical components are easy to control, repeatability is good, and the yield is high.
Description
Technical field
The present invention relates to a kind of complex [Co (L1)2(H2O)] and prepare cancer therapy drug application.
Background technology
In pyrazole compound, e derivatives are most important classes in pyrazole derivatives, and its attention rate is also relatively
High.E derivatives all contain a pyrazole ring, belong to five-ring heterocycles, have certain armaticity, have certain alkalescence simultaneously,
Hydrogen on 4, its derivative very vivaciously it is easy to being acylated and forming beta-diketon structure, brings colourful to its derivative
Physics and chemical property.Research shows, the pyrazolone compound that synthesis has chiral centre has potential pharmaceutical applications valency
Value.Based on its pharmaceutical applications great potential, research how to construct the higher structure of medical value be its research focus it
One.
Metal complex with 1- (2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester as Material synthesis has uniqueness
Biologically active, can serve as designing synthesis there is the effective antibacterial of low toxicity of application prospect, medicine, the functional material such as antitumor
Presoma, there is important potential use.
Content of the invention
The purpose of the present invention is exactly for designing pyridine synthesis-pyrazole derivatives metal complex, using solvent heat side
Method synthetic technology synthetic compound [Co (L1)2(H2O)](L1=1- (2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester) and
Prepare cancer therapy drug application.
Complex [Co (L according to the present invention1)2(H2O molecular formula)] is:C20H18CoN6O7, molecular weight is:513.33,
There is good biologically active, its crystallographic parameter is shown in Table one, and part bond distance, bond angle are shown in Table two, the IC50 to part cancer cell
Value is shown in Table three.
Table one:Complex [Co (L1)2(H2O crystallographic parameter)]
aR1=Σ | | Fo|–|Fc||/Σ|Fo|.bwR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table two:Complex [Co (L1)2(H2O part bond distance)], bond angle
Table three:Complex [Co (L1)2(H2O the)] IC to different cell lines50Value
In table:MGC30-8 is gastric carcinoma cells, and HepG2 is human liver cancer cell, and NCI-H460 is human lung carcinoma cell, BEL-
7404 is human liver cancer cell, and HL-7702 is human normal hepatic cell strain.
[Co(L1)2(H2O synthetic method)] concretely comprises the following steps:
(1) by 0.05-0.15 gram of analysis pure 1- (2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester and 0.05-0.15
Gram analyze pure two water cobalt acetates be dissolved in 15-20 milliliter volume ratio be 8:In the mixed solution of 2 anhydrous acetonitrile and the pure methyl alcohol of analysis.
(2) solution obtained by step (1) is proceeded in the reactor of polytetrafluoroethylene (PTFE), react 60-80 at 80-90 DEG C
Hour, it is cooled to room temperature, filters, filtrate puts at room temperature volatilization crystallization naturally, obtains monocrystalline level complex [Co (L after 16 days1)2
(H2O)].
Instant invention overcomes the shortcoming of solvent method, there is process is simple, with low cost, chemical constituent is easily controllable, repetition
Property well and yield high the advantages of.
Brief description
Fig. 1-2 is complex of the present invention [Co (L1)2(H2O structure chart)].
In figure:C- carbon atom, N- nitrogen-atoms, O- oxygen atom, Co- cobalt atom, numeral and lowercase letter atomic order
Sequence number.
Fig. 3 is complex of the present invention [Co (L1)2(H2O three-dimensional structure accumulation graph)].
Specific embodiment
Embodiment 1:
The present invention relates to complex [Co (L1)2(H2O molecular formula)] is:C20H18CoN6O7, molecular weight is:513.33, tool
There is good biologically active.
[Co(L1)2(H2O synthetic method)] concretely comprises the following steps:
(1) will be pure to 0.109 gram of analysis pure 1- (2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester and 0.125 gram of analysis
It is 8 that two water cobalt acetates are dissolved in 15 milliliters of volume ratios:In the mixed solution of 2 anhydrous acetonitrile and the pure methyl alcohol of analysis.
(2) solution obtained by step (1) is proceeded in the reactor of polytetrafluoroethylene (PTFE), reacts 72 hours at 80 DEG C,
It is cooled to room temperature, filters, filtrate puts at room temperature volatilization crystallization naturally, obtains monocrystalline level [Co (L after 16 days1)2(H2O)] coordinate
Thing.
Embodiment 2:
The present invention relates to complex [Co (L1)2(H2O molecular formula)] is:C20H18CoN6O7, molecular weight is:513.33, tool
There is good biologically active.
[Co(L1)2(H2O synthetic method)] concretely comprises the following steps:
(1) will be pure to 0.055 gram of analysis pure 1- (2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester and 0.065 gram of analysis
It is 8 that two water cobalt acetates are dissolved in 18 milliliters of volume ratios:In the mixed solution of 2 anhydrous acetonitrile and analysis ethanol.
(2) solution obtained by step (1) is proceeded in the reactor of polytetrafluoroethylene (PTFE), reacts 60 hours at 90 DEG C,
It is cooled to room temperature, filters, filtrate puts at room temperature volatilization crystallization naturally, obtains monocrystalline level [Co (L after 16 days1)2(H2O)] coordinate
Thing.
Claims (2)
1. a kind of complex [Co (L1)2(H2O)] it is characterised in that complex [Co (L1)2(H2O molecular formula)] is:
C20H18CoN6O7, molecular weight is:513.33, its crystallographic parameter is shown in Table one, and part bond distance, bond angle are shown in Table two;Wherein L1=1-
(2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester;
Table one:Complex [Co (L1)2(H2O crystallographic parameter)]
aR1=Σ | | Fo|–|Fc||/Σ|Fo|.bwR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table two:Complex [Co (L1)2(H2O part bond distance)], bond angle
Described [Co (L1)2(H2O synthetic method)] concretely comprises the following steps:
(1) by 0.05-0.15 gram of analysis pure 1- (2- pyridine) -5- hydroxyl -1H- pyrazoles -3- carboxylate methyl ester and 0.05-0.15 gram point
Analyse pure two water cobalt acetates to be dissolved in 15-20 milliliter volume ratio is 8:In the mixed solution of 2 anhydrous acetonitrile and the pure methyl alcohol of analysis;
(2) solution obtained by step (1) is proceeded in the reactor of polytetrafluoroethylene (PTFE), at 80-90 DEG C, reaction 60-80 is little
When, it is cooled to room temperature, filters, filtrate puts at room temperature volatilization crystallization naturally, obtains monocrystalline level complex [Co (L after 16 days1)2
(H2O)].
2. complex [Co (L according to claim 11)2(H2O application)] is it is characterised in that complex [Co (L1)2
(H2O)] cancer therapy drug application is prepared in conduct.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610818040.6A CN106432185A (en) | 2016-09-13 | 2016-09-13 | Complex [Co(L1)2(H2O)] and application thereof in preparation of anticancer drugs |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610818040.6A CN106432185A (en) | 2016-09-13 | 2016-09-13 | Complex [Co(L1)2(H2O)] and application thereof in preparation of anticancer drugs |
Publications (1)
Publication Number | Publication Date |
---|---|
CN106432185A true CN106432185A (en) | 2017-02-22 |
Family
ID=58168703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610818040.6A Pending CN106432185A (en) | 2016-09-13 | 2016-09-13 | Complex [Co(L1)2(H2O)] and application thereof in preparation of anticancer drugs |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106432185A (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101260121A (en) * | 2007-03-07 | 2008-09-10 | 卡南吉医药科技(上海)有限公司 | Complex compound of heteroaromatic thiosemicarbazone and transition metal, and application thereof in preparing antineoplastic medicine |
CN101885689A (en) * | 2010-07-08 | 2010-11-17 | 云南大学 | Fat soluble dual-core cobalt (III) anti-tumor coordination compound and preparation method thereof |
CN102260293A (en) * | 2011-05-04 | 2011-11-30 | 广西师范大学 | Transition metal coordination compounds with oxoglaucine as ligand, synthesizing method thereof, and application thereof |
CN105669723A (en) * | 2016-03-23 | 2016-06-15 | 桂林理工大学 | Synthesizing method of complex [Zn(L)2].(H2O) and application of complex [Zn(L)2] (H2O) to preparation of anticancer medicine |
-
2016
- 2016-09-13 CN CN201610818040.6A patent/CN106432185A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101260121A (en) * | 2007-03-07 | 2008-09-10 | 卡南吉医药科技(上海)有限公司 | Complex compound of heteroaromatic thiosemicarbazone and transition metal, and application thereof in preparing antineoplastic medicine |
CN101885689A (en) * | 2010-07-08 | 2010-11-17 | 云南大学 | Fat soluble dual-core cobalt (III) anti-tumor coordination compound and preparation method thereof |
CN102260293A (en) * | 2011-05-04 | 2011-11-30 | 广西师范大学 | Transition metal coordination compounds with oxoglaucine as ligand, synthesizing method thereof, and application thereof |
CN105669723A (en) * | 2016-03-23 | 2016-06-15 | 桂林理工大学 | Synthesizing method of complex [Zn(L)2].(H2O) and application of complex [Zn(L)2] (H2O) to preparation of anticancer medicine |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105669723A (en) | Synthesizing method of complex [Zn(L)2].(H2O) and application of complex [Zn(L)2] (H2O) to preparation of anticancer medicine | |
CN102399246A (en) | Metal nickel-imidazole chiral nanometer cage complex and preparation method thereof | |
CN104341423A (en) | Ticagrelor monohydrate, preparation method thereof and pharmaceutical application thereof | |
CN106432304A (en) | Coordination compound [La(L<1>)(HL<1>)(H2O)(NO3)2] and application to preparation of anti-cancer medicine | |
CN104327051A (en) | Crystal form of fumarate of pyrrole derivative | |
CN104761575A (en) | Eugenol nicotinicate-silver (I) complex, and preparation method and use thereof | |
CN106432185A (en) | Complex [Co(L1)2(H2O)] and application thereof in preparation of anticancer drugs | |
CN103450236A (en) | 6-Hydroxyloxoisoaporphine rare earth complexes, and synthetic method and application thereof | |
CN106432299A (en) | Complex [Pr(L2)2(H2O)(NO3)2] and application in preparation of anti-cancer drug | |
CN109096207A (en) | A kind of salt, preparation method and the crystal structure of 5 FU 5 fluorouracil and melbine | |
CN105646549A (en) | Double-terminal-group pyridine copper complex and preparation method thereof | |
CN106432301A (en) | Complex [Nd(L1)2(H2O)(NO3)2] and application in preparing anti-cancer drug | |
CN103880869A (en) | Anti-cancer drug [Cu2(L<4>)(L<6>)] and in-situ synthesis method thereof | |
CN106496185A (en) | Complex [Zn (L1)2(H2O)](H2O) and cancer therapy drug application is prepared | |
CN106432302A (en) | [Pr(HL1)2(NO3)3(CH3OH)2(H2O)]H2O and application to anti-cancer medicine | |
CN106432303A (en) | Complex [Ce(L1)2(H2O)(NO3)2] and application of complex in preparation of anticancer drugs | |
CN106432361A (en) | Complex [Ni(L1)2(H2O)2] and application in preparation of anti-cancer drug | |
CN106432300A (en) | Complex [Nd(HL2)2(H2O)(NO3)2] and application in anti-cancer drug preparation | |
CN106397487A (en) | Complex [Mn2(HL<1>)2(<mu>2-Cl)2(Cl)2] and application of same to preparation of anti-cancer drug | |
CN103880818A (en) | Anti-cancer drug [Cu2(L<7>)2].(CH3CH2OH)2 | |
CN103159789A (en) | Biapenem crystalline solid and preparation method thereof | |
CN105622642A (en) | Voriconazole copper nitrate complex with bacteriostatic activity and preparation method thereof | |
CN106496285A (en) | M-phthalic acid cobalt coordination polymer and preparation method thereof | |
CN103214526B (en) | palladium/platinum mixed ligand coordination compound and preparation method thereof | |
CN101775040B (en) | New method for preparing picoplatin |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170222 |