CN101434622B - Antimony triphenyl complexes, as well as preparation method and application thereof - Google Patents
Antimony triphenyl complexes, as well as preparation method and application thereof Download PDFInfo
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- CN101434622B CN101434622B CN2008101603528A CN200810160352A CN101434622B CN 101434622 B CN101434622 B CN 101434622B CN 2008101603528 A CN2008101603528 A CN 2008101603528A CN 200810160352 A CN200810160352 A CN 200810160352A CN 101434622 B CN101434622 B CN 101434622B
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Abstract
The invention discloses a triphenylantimony composition with a structural formula as follow. The preparation method of the triphenylantimony composition comprises the steps that: 0.2mmol to 0.8mmol of bis(triphenylantimony catecholate) oxide and 0.4mmol to 2mmol of sodium methoxide are added into a reaction vessel and stirred for 0.5h to 1h; then 10mL to 20mL of methanol is added into the mixture, stirred for 20h to 30h under normal temperature and then filtered in vacuum to obtain a solid matter; the solid matter is re-crystallized by dichloromethane-petroleum ether to obtain a colorless crystal which is the triphenylantimony composition; the yield of the reaction is 72 percent to 82 percent. The triphenylantimony composition has high anti-cancer activity and can be used as raw materials for preparing medicaments treating stomach cancer, nasopharyngeal cancer, liver cancer or leucocythemia. Compared with the existing platinum-based anti-cancer compounds, the triphenylantimony composition has the advantages of high anti-cancer activity, good lipid solubility, low cost and simple preparation method and the like, thus providing new ways for developing anti-cancer medicaments.
Description
Technical field
The present invention relates to a kind of antimony triphenyl title complex and preparation method thereof, and the application of this compound in the preparation cancer therapy drug.
Background technology
Organometallics (Organometallic compound) is meant the compound that contains one or more metal-carbon keys (M-C key), because of its widespread use at aspects such as synthetic, catalysis, antifouling, medicine, PVC stablizers gets more and more people's extensive concerning.People have just begun the research of organic stibium complex as far back as mid-term in 19th century, as medicine, up to the eighties in 20th century, more research just appears in organic stibium complex, antimonypotassium tartrate (sodium) becomes one of important drugs of state-promulgated pharmacopoeia income, can treat schistosomicide and kala-azar, antimony triphenyl was once carried out Anticancer Activities by the American National ICR, people such as P.Raj synthesize and have measured a kind of biological activity of tetraphenyl stibnide, have sterilization, desinsection and anticholinesterasic biological activity.
Successful utilizations in organic stibium complex such as many traditional characterization methods such as infrared spectra, nuclear magnetic resonance spectrum, mass spectrum are for its research provides important guarantee; And the development and application of x-ray diffraction technique more it provides intuitively and accurately structural information.
Because organic stibium complex has certain pharmacology and physiological activity, again because of itself containing multiple coordination possibility, and sterically hindered little between dentate and be easy to the formation of dinuclear complex, be people's research object in recent years always.The eager desire that to develop a kind of organic stibium complex with better pharmacology and physiologically active be people.
Summary of the invention
At above-mentioned prior art, the invention provides a kind of new antimony triphenyl title complex, and the preparation method and the application of this compound are provided.
A kind of antimony triphenyl title complex, structural formula is as follows:
A kind of preparation method of antimony triphenyl title complex, step is as follows: the bi triphenyl antimony chloride oxide (sodium methylate of triphenylantimony (v) dichloride), 0.4～2mmol that adds 0.2～0.8mmol in reaction vessel, stir 0.5～1h, add methyl alcohol 10～20mL again, stirring at normal temperature 20～30h, vacuum filtration, get solids, be methylene dichloride-sherwood oil recrystallization of 1:1～1:2 then with volume ratio, get clear crystal, be the antimony triphenyl title complex, productive rate 72～82%.
The application of described antimony triphenyl title complex in preparation treatment cancer of the stomach, nasopharyngeal carcinoma, people's liver cancer or leukemic medicine.
Antimony triphenyl complex molecule formula of the present invention is: C
38H
36O
3Sb
2, 197 ℃ of fusing points have higher anti-cancer activity, can be feedstock production treatment cancer of the stomach, nasopharyngeal carcinoma, people's liver cancer or leukemic medicine with it.With anticancer the comparing of platinum class of generally using at present, organotin coordination compound of the present invention has higher, fat-soluble good, the characteristics such as cost is low, the preparation method is simple of antitumour activity, for the exploitation cancer therapy drug provides new way.
Embodiment
The present invention is further illustrated below in conjunction with embodiment:
Embodiment 1: preparation antimony triphenyl title complex: add the bi triphenyl antimony chloride oxide of 0.0848g (0.2mmol) in flask, the sodium methylate of 0.4mmol stirs 0.5h, the methyl alcohol that adds 10mL again, stirring at normal temperature 24h, vacuum filtration gets solids, use methylene dichloride-sherwood oil (V:V=1:1) recrystallization then, behind the 74h, get clear crystal, be the antimony triphenyl title complex, 197 ℃ of fusing points, productive rate 72%.
Through Infrared spectroscopy and nuclear magnetic resonance spectroscopy, the result is as follows:
IR(KBr，cm-1)：732-768cm-1(Sb-O-Sb)，3640cm-1(OH)
H
1NMR：7.32ppm(m-ph)，7.71ppm(p-ph)，8.21ppm(o-ph)，3.12ppm(CH3)，10.3ppm(OH)
C
13NMR：131.8(m-ph)，133.9(p-ph)，135.6(o-ph)，140.1(C-Sb)，170.0(C＝O)，37.42(CH3)
Embodiment 2: preparation antimony triphenyl title complex: add the bi triphenyl antimony chloride oxide of 0.1696g (0.4mmol) in flask, the sodium methylate of 1.0mmol stirs 1h, the methyl alcohol that adds 15mL again, stirring at normal temperature 20h, vacuum filtration gets solids, use methylene dichloride-sherwood oil (V:V=1:2) recrystallization then, behind the 74h, get clear crystal, be the antimony triphenyl title complex, 197 ℃ of fusing points, productive rate 80%.
Embodiment 3: preparation antimony triphenyl title complex: add the bi triphenyl antimony chloride oxide of 0.3392g (0.8mmol) in flask, the sodium methylate of 2.0mmol stirs 1h, the methyl alcohol that adds 20mL again, stirring at normal temperature 30h, vacuum filtration gets solids, use methylene dichloride-sherwood oil (V:V=1:2) recrystallization then, behind the 74h, get clear crystal, be the antimony triphenyl title complex, 197 ℃ of fusing points, productive rate 82%.
Embodiment 4: preparation antimony triphenyl title complex: the bi triphenyl antimony chloride oxide that adds 0.2544g (0.6mmol) in flask, 1.5mmol sodium methylate, stir 45min, add the methyl alcohol of 18mL again, stirring at normal temperature 28h, vacuum filtration, get solids, use methylene dichloride-sherwood oil (V:V=1:1.5) recrystallization then, behind the 74h, get clear crystal, promptly
Be the antimony triphenyl title complex, 197 ℃ of fusing points, productive rate 76%.
The test example: antimony triphenyl title complex of the present invention, its external antitumour activity are measured by MTT and two kinds of experimental techniques of SRB and are realized that its principle is:
MTT analytical method: with metabolism reduction 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl terrazolium bromide is the basis, has the desaturase relevant with NADP in the viable cell plastosome, yellow MTT can be reduced into insoluble hepatic Formazan, dead cell does not have this enzyme, MTT is not reduced, and behind DMSO dissolving Formazan, available microplate reader is measured the optical density(OD) of characteristic wavelength, carry out relevant data and handle, reach a conclusion.
The SRB analytical method: Sulforhodamine B is a kind of pink protein bound dyestuff, water soluble, can combine with the basic aminoacids in the biomacromolecule, it is good linear relationship at the OD of 515nm reading and cell count, but quantitative Analysis goes out the data of medicine dosage and cells involved number.
With the SRB analytical method people's liver cancer Bel-7402 cell strain, people's cancer of the stomach BGC-823 cell strain, human nasopharyngeal carcinoma KB cell strain are analyzed, human leukemia HL-60 cell's strain is analyzed, measure its IC with the MTT analytical method
50Value the results are shown in Table 1, and conclusion is: by data in the table as can be known, cancer therapy drug of the present invention has certain antitumour activity to people's liver cancer, leukemia, and is bigger to the human nasopharyngeal carcinoma antitumour activity, can be used as the candidate compound of cancer therapy drug.
Table 1 antimony triphenyl title complex cancer therapy drug external activity test data
| Cell strain | Concentration (μ M/L) | Inhibiting rate (%) |
| People's liver cancer | 1.252.551020 | -0.094.223.148.547.91 |
| Human leukemia | 1.252.551020 | 8.583.582.90-0.320.97 |
| Human nasopharyngeal carcinoma | 1.252.551020 | -1.5714.489.1718.3221.25 |
| People's cancer of the stomach | 1.252.551020 | -13.94-4.91-2.40-7.534.37 |
Claims (2)
1. antimony triphenyl title complex, it is characterized in that: described title complex is to prepare by the following method: add the bi triphenyl antimony chloride oxide of 0.2～0.8mmol, the sodium methylate of 0.4～2mmol in reaction vessel, stir 0.5～1h, add methyl alcohol 10～20mL again, stirring at normal temperature 20～30h, vacuum filtration, get solids, be methylene dichloride-sherwood oil recrystallization of 1: 1～1: 2 then with volume ratio, get clear crystal, be the antimony triphenyl title complex.
2. the application of the described a kind of antimony triphenyl title complex of claim 1 in preparation treatment cancer of the stomach, nasopharyngeal carcinoma, people's liver cancer or leukemic medicine.
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| CN101434622B true CN101434622B (en) | 2011-05-11 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US9499574B2 (en) | 2012-08-14 | 2016-11-22 | Northwestern University | Arsenoplatin anti-cancer agents |
| WO2014028653A1 (en) | 2012-08-14 | 2014-02-20 | Northwestern University | Arsenoplatin anti-cancer agents |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1398200A (en) * | 2000-02-10 | 2003-02-19 | 巴斯福股份公司 | Phosphor, arsenic and antimony compounds based upon diaryl-anellated bicyclo 2.2.N8cexcl, parent substances and catalysts contg. same |
| CN1863809A (en) * | 2001-03-29 | 2006-11-15 | 巴斯福股份公司 | Ligands for pnicogen chelate complexes with a metal of subgroup viii and use of the complexes as catalysts for hydroformylation, carbonylation, hydrocyanation or hydrogenation |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1398200A (en) * | 2000-02-10 | 2003-02-19 | 巴斯福股份公司 | Phosphor, arsenic and antimony compounds based upon diaryl-anellated bicyclo 2.2.N8cexcl, parent substances and catalysts contg. same |
| CN1863809A (en) * | 2001-03-29 | 2006-11-15 | 巴斯福股份公司 | Ligands for pnicogen chelate complexes with a metal of subgroup viii and use of the complexes as catalysts for hydroformylation, carbonylation, hydrocyanation or hydrogenation |
Non-Patent Citations (1)
| Title |
|---|
| L. Quan et al..μ-oxido-bis[(chloroacetato-κO)triphenylantimony(V)].《Acta Crystallographica Section E》.2008,第E64卷m349,sup-1-sup-8. * |
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