CN104402939A - Iridium complex as well as preparation method and application thereof - Google Patents
Iridium complex as well as preparation method and application thereof Download PDFInfo
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- CN104402939A CN104402939A CN201410657953.5A CN201410657953A CN104402939A CN 104402939 A CN104402939 A CN 104402939A CN 201410657953 A CN201410657953 A CN 201410657953A CN 104402939 A CN104402939 A CN 104402939A
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Abstract
The invention discloses an iridium complex as well as a preparation method and an application thereof. The iridium complex is monochloro-mono-meta-methoxybenzaldehyde-4-phenyl-3-thiosemicarbazide-pentamethyl cyclopentadienyl iridium (III) and can be applied to preparation of medicines for treating cancers, and the structural formula of the complex is shown in the specification.
Description
Technical field
The present invention relates to chemical medicine field, especially a kind of iridium metal complex and its production and use.
Technical background
Since Rosenberg in 1967 finds that cis-platinum has antitumor action, cis-platinum has become and has been used for the treatment of cancer one of 3 kinds of medicines the most widely in the world.Through the research of researcher decades, the several generations such as carboplatin, oxaliplatin platinum complex is synthesized out and is applied to clinical.But, apply to clinical chemotherapy or tens of kinds of auxiliary antitumor drugs at present, only to the treatment of Partial tumors, there is good curative effect.Therefore, prepare new metal complexes antitumor drug, for the treatment of tumor disease can provide how better selection, become current study hotspot.The present invention attempts using iridium metals to replace traditional platinum, does not also find the report of being correlated with at present.
Summary of the invention
The object of the invention is to the deficiency for general chemicals, a kind of iridium metal complex and its production and use is provided, by utilizing heavy metal iridic compound can the feature of inhibition tumor cell DNA replication dna and thiosemicarbazide compound feature cheap and easy to get, after making their coordinate, form a kind of iridium metal complex with anticancer parasiticide effect newly.
Technical scheme provided by the invention is:
A kind of iridium metal complex, wherein:
The chemical name of described iridium metal complex is: a chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl closes iridium (III);
The structural formula of described iridium metal complex is:
Preferably, in described iridium metal complex, described title complex is orange crystal and is soluble in organic solvent, and its hydrogen nuclear magnetic resonance modal data is
1h NMR (CDCl
3solvent): δ=10.11 (br, 1H), 9.03 (br, 1H), 7.92 (s, 1H), 7.55 (m, 3H, J=7.8Hz), 7.45 (t, 1H, J=7.8Hz), 7.40 (t, 2H, J=7.9Hz), 7.31 (d, 1H, J=7.2Hz), 5.41 (d, 1H, J=6.0Hz), 4.95 (d, 1H, J=6.0Hz), 4.81 (d, 1H, J=5.4Hz), 4.75 (d, 1H, J=5.4Hz), 3.93 (s, 3H), 2.63 (m, 1H, J=6.9Hz), 2.19 (s, 3H), 1.18, 1.13 (2d, 6H, J=6.9Hz) ppm..
A preparation method for iridium metal complex, wherein, comprises the following steps:
Step one, by m-hydroxybenzaldehyde and acetone mixing mix after, mix with salt of wormwood mixing again and obtain light yellow transparent solution, after heated and stirred backflow certain hour, described light yellow transparent solution is mixed with methyl-sulfate, filter after reaction certain hour and obtain filtrate, after filtrate is spin-dried for and deionized water be mixed to get the first mixed solution, extraction agent is used to be extracted liquid layer to the extraction that the first mixed solution carries out more than 3 times, be spin-dried for after extraction liquid layer and the mixing of a certain amount of siccative, obtain NSC 43794, structural formula is as follows:
Step 2, gained NSC 43794, dehydrated alcohol and 4-phenyl-3-thiosemicarbazide to be mixed, under certain temperature after return stirring for some time, obtain micro-purple solution, described micro-purple solution is concentrated into a certain amount of after, mix with ethanol and normal hexane, separate out white crystal, be NSC 43794 contracting 4-phenyl-3-thiosemicarbazide, structural formula is as follows:
Step 3, described NSC 43794 contracting 4-methyl-3-thiosemicarbazide and dichloro (pentamethylcyclopentadiene base) are closed iridium (III) dimer and CH
2cl
2be mixed to get the second mixed solution, after stirring for some time under certain temperature, by described second mixed solution underpressure distillation to certain volume, leave standstill and separate out orange solids, namely product one chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl of the present invention closes iridium (III).
Preferably, in the preparation method of described iridium metal complex, in step one, each amounts of components used is respectively: m-hydroxybenzaldehyde 4-10g, acetone 5-20ml, salt of wormwood 2-5g, methyl-sulfate 2-10ml, deionized water 2-5ml, extraction agent 2-10m and siccative 5-20g, described heated and stirred reflux temperature is 30-50 DEG C, time is 5-20 minute, described light yellow transparent solution and methyl-sulfate hybrid reaction time are 10-15h, wherein, described alr mode is magnetic agitation, the concentration of described acetone is 90-100%, extraction agent is the ethyl acetate of concentration 90-100%, siccative is Anhydrous potassium carbonate.
Preferably, in the preparation method of described iridium metal complex, in step 2, each amounts of components used is respectively: NSC 43794 2-5g, dehydrated alcohol 5-20ml, 4-phenyl-3-thiosemicarbazide 1-5g, ethanol 2-10ml and normal hexane 2-10ml, the temperature of described return stirring is 50-70 DEG C, time is 3-6h, and the concentrated amount of described micro-purple solution is 1-3ml, wherein, the concentration of described ethanol is 90-100%, the concentration of normal hexane is 90-100%, and described micro-purple solution condensing mode is for being spin-dried for, and described alr mode is magnetic agitation.
Preferably, in the preparation method of described iridium metal complex, churning time described in step 3 is 5-8 hour, whipping temp is 15-35 DEG C, each amounts of components used is respectively: NSC 43794 contracting 4-methyl-3-thiosemicarbazide 15-30mg, dichloro (pentamethylcyclopentadiene base) closes iridium (III) dimer 20-40mg and CH
2cl
25-10ml, the temperature of described stirring is 10-40 DEG C, and the time is 3-8h, and described distillation volume is 1-3ml, wherein, described CH
2cl
2concentration 90-100%, alr mode is magnetic agitation.
A purposes for iridium metal complex, described iridium metal complex is for the preparation of the application of Therapeutic cancer and anti-parasite medicine.
A purposes for iridium metal complex, described iridium metal complex can be made into the form of injection, tablet, pill, capsule, suspension agent or emulsion.
The present invention has following beneficial effect: first, iridium metal complex of the present invention to the medium effective concentration of tumour cell between 10-45umol/mL, show that it has good inhibition tumor cell active effect, its form that can be made into injection, tablet, pill, capsule, suspension agent or emulsion uses as cancer therapy drug.
Secondly, iridium metal complex of the present invention has good parasiticide effect, and it is 5-12umol/mL to plasmodial medium effective concentration, the preparation of its energy widespread use and anti-parasite medicine.
Finally, the preparation method of iridium metal complex of the present invention is simple, and raw material is easy to get, and has the advantage that cost is low, compares traditional anticancer anti-parasite medicine, and cost reduces by 50%.
Embodiment
Below in conjunction with embodiment, the present invention is elaborated, can implement according to this after consulting this specification sheets to make those of ordinary skill in the art.
A kind of iridium metal complex, wherein:
The chemical name of described iridium metal complex is: a chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl closes iridium (III);
The structural formula of described iridium metal complex is:
In described iridium metal complex, iridium metals and compound thereof can act on the DNA replication dna process of tumour cell, the reproduction process of the RNA of tumour cell can also be acted on when the concentration of iridium metals and compound thereof is enough large, and damage its cytolemma, thus reach the object of tumors destroyed cell, and thiosemicarbazide compound, it is the intermediate of medicine synthesis, very cheap and easy to get, use thiosemicarbazide compound as the ligand of iridium metals, significantly can reduce cost, thus provide a thinking for solving the expensive problem of cancer therapy drug.
In described iridium metal complex, described compound is orange crystal and is soluble in organic solvent, and its hydrogen nuclear magnetic resonance modal data is
1h NMR (CDCl
3solvent): δ=10.11 (br, 1H), 9.03 (br, 1H), 7.92 (s, 1H), 7.55 (m, 3H, J=7.8Hz), 7.45 (t, 1H, J=7.8Hz), 7.40 (t, 2H, J=7.9Hz), 7.31 (d, 1H, J=7.2Hz), 5.41 (d, 1H, J=6.0Hz), 4.95 (d, 1H, J=6.0Hz), 4.81 (d, 1H, J=5.4Hz), 4.75 (d, 1H, J=5.4Hz), 3.93 (s, 3H), 2.63 (m, 1H, J=6.9Hz), 2.19 (s, 3H), 1.18, 1.13 (2d, 6H, J=6.9Hz) ppm..
A preparation method for iridium metal complex, wherein, comprises the following steps:
Step one, get a 50ml round-bottomed flask, add 5g m-hydroxybenzaldehyde, use 10ml acetone solution, add 3.826g Anhydrous potassium carbonate, solution is light yellow transparent solution, and at 45 DEG C, heated and stirred refluxes 10 minutes, then slowly drips methyl-sulfate 3.87ml, after reaction 12h, filtrate is spin-dried for, adds 2ml deionized water, add 5ml extraction into ethyl acetate, repeat 4 extraction into ethyl acetate processes, combined ethyl acetate layer solution, adds the drying of 10g Anhydrous potassium carbonate, is spin-dried for by solution, obtain NSC 43794, its structural formula is:
Step 2,3g NSC 43794 is dissolved in 10ml dehydrated alcohol, and add 4-phenyl-3-thiosemicarbazide 1.0g, 65 DEG C of return stirrings, reaction 5h obtains micro-purple solution, be spin-dried for 1ml, add 5ml ethanol and 5ml normal hexane, separate out white crystal, for NSC 43794 contracting 4-phenyl-3-thiosemicarbazide, its structural formula:
Step 3, take NSC 43794 contracting 4-methyl-3-thiosemicarbazide 21mg and dichloro (pentamethylcyclopentadiene base) and close osmium (III) dimer 31.5mg and add CH
2cl
26ml, stirring at normal temperature 6 hours, is distilled to about 1ml by solution decompression, leaves standstill and separates out orange solids, and namely product one chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl closes iridium (III), and its structural formula is:
In the preparation method of described iridium metal complex, container in step one is round-bottomed flask, each amounts of components used is respectively: m-hydroxybenzaldehyde 4-10g, the acetone 5-20ml of concentration 90-100%, salt of wormwood 2-5g, methyl-sulfate 2-10ml, deionized water 2-5ml, extraction agent 2-10m and siccative 5-20g, described heated and stirred reflux temperature is 30-50 DEG C, time is 5-20 minute, described light yellow transparent solution and methyl-sulfate hybrid reaction time are 10-15h, wherein, described alr mode is magnetic agitation, described extraction agent is the ethyl acetate of concentration 90-100%, siccative is Anhydrous potassium carbonate.
In the preparation method of described iridium metal complex, in step 2, each amounts of components used is respectively: NSC 43794 2-5g, dehydrated alcohol 5-20ml, 4-phenyl-3-thiosemicarbazide 1-5g, the normal hexane 2-10ml of concentration to be the ethanol 2-10ml of 90-100% and concentration be 90-100%, the temperature of described return stirring is 50-70 DEG C, time is 3-6h, the concentrated amount of described micro-purple solution is 1-3ml, wherein, described micro-purple solution condensing mode is for being spin-dried for, and described alr mode is magnetic agitation.
In the preparation method of described iridium metal complex, churning time described in step 3 is 5-8 hour, whipping temp is 15-35 DEG C, each amounts of components used is respectively: NSC 43794 contracting 4-methyl-3-thiosemicarbazide 15-30mg, dichloro (pentamethylcyclopentadiene base) closes the CH of iridium (III) dimer 20-40mg and concentration 90-100%
2cl
25-10ml, the temperature of described stirring is 10-40 DEG C, and the time is 3-8h, and described distillation volume is 1-3ml, and wherein said alr mode is magnetic agitation.
A purposes for iridium metal complex, described iridium metal complex is for the preparation of the application of Therapeutic cancer and anti-parasite medicine.
A purposes for iridium metal complex, described iridium metal complex can be made into the form of injection, tablet, pill, capsule, suspension agent or emulsion.
Embodiment 1
One, product preparation
Get a 50ml round-bottomed flask, add 5g m-hydroxybenzaldehyde, use 10ml acetone solution, add 3.826g Anhydrous potassium carbonate, solution is light yellow transparent solution, at 45 DEG C, heated and stirred refluxes 10 minutes, then slowly drips methyl-sulfate 3.87ml, after reaction 12h, filtrate is spin-dried for, add 2ml deionized water, add 5ml extraction into ethyl acetate, repeat 4 extraction into ethyl acetate processes, combined ethyl acetate layer solution, add 10g Anhydrous potassium carbonate dry, solution is spin-dried for, obtains NSC 43794; 3g NSC 43794 is dissolved in 10ml dehydrated alcohol, and add 4-phenyl-3-thiosemicarbazide 1.0g, 65 DEG C of return stirrings, reaction 5h obtains micro-purple solution, be spin-dried for 1ml, add 5ml ethanol and 5ml normal hexane, separating out white crystal, is NSC 43794 contracting 4-phenyl-3-thiosemicarbazide; Take NSC 43794 contracting 4-methyl-3-thiosemicarbazide 21mg and dichloro (pentamethylcyclopentadiene base) to close osmium (III) dimer 31.5mg and add CH
2cl
26ml, stirring at normal temperature 6 hours, is distilled to about 1ml by solution decompression, leaves standstill and separates out orange solids, and namely product one chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl closes iridium (III).
Two, anti tumor activity in vitro experiment
Experimentation: adopt MTT method, carry out vitro cytotoxicity mensuration.By iridium metal complex obtained above and cancer of the stomach SGC 7901 cell strain and liver cancer BEL-7404 cell strain 72 hours action time respectively, then measure iridium metal complex to the medium effective concentration (IC of tumor cell line
50).Wherein, medium effective concentration (IC
50) be limit value with 100umol/mL, be less than 100umol/mL and illustrate effective, be greater than 100umol/mL and illustrate there is no effect.
Experimental result:
Table 1 product of the present invention is to the medium effective concentration (IC of tumor cell line
50) (umol/mL)
| Cell strain | SGC-7901 | BEL-7404 |
| IC 50(umol/mL) | 18.5±3.8 | 30.2±4.9 |
From the results shown in Table 1, iridium metal complex of the present invention shows through anticancer experiment in vitro, this compound has strong anti-tumor activity, and the medium effective concentration of the compound on tumor cell of gained of the present invention is at 15-35umol/mL, and description effect is obvious.The present invention is that the new antitumor drug of research and development provides new thinking.
Three, parasiticide experiment
Experimentation: adopt fluorocyte classification analysis (FACS) quantitative erythrocytic plasmodium culture method to assess the Antiparasitic Activity of product of the present invention.The iridium metal complex that embodiment 1 obtains is dissolved in 1mlDMSO, then with by 25mmol/L 4-hydroxyethyl piperazine ethanesulfonic acid damping fluid, 32mmol/LNaHCO
3200 times are diluted with RPMI 1640 cell culture medium that 10% human plasma is made into.Sample solution is made into 11 kinds of different concns by the method for 2 times of dilutions subsequently successively, by 1ml, and 2 × 10
6the plasmodium of/ml adds in solution, is put in 5%CO at 37 DEG C
248h is cultivated in incubator.Add 1ml 3% DAPI solution, then cultivate 18h, measure RBC number with fluorocyte classification analysis instrument, can show that different concns sample is to plasmodial inhibiting rate, calculates IC
50value.
Table 2 product of the present invention is to parasitic medium effective concentration (IC
50)
| Parasite | Plasmodium |
| IC 50(umol/mL) | 8.8±1.8 |
As can be seen from the result of table, iridium metal complex of the present invention is 6-10umol/mL to plasmodial medium effective concentration, illustrates that this compound has strong Antiparasitic Activity.
Although embodiment of the present invention are open as above, but it is not restricted to listed in specification sheets and embodiment utilization, it can be applied to various applicable the field of the invention completely, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the universal that claim and equivalency range limit, the present invention is not limited to specific details and illustrates here and the example described.
Claims (8)
1. an iridium metal complex, is characterized in that:
The chemical name of described iridium metal complex is: a chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl closes iridium (III);
The structural formula of described iridium metal complex is:
2. iridium metal complex as claimed in claim 1, it is characterized in that, described title complex is orange crystal and is soluble in organic solvent, and its hydrogen nuclear magnetic resonance modal data is
1h NMR (CDCl
3solvent): δ=10.11 (br, 1H), 9.03 (br, 1H), 7.92 (s, 1H), 7.55 (m, 3H, J=7.8Hz), 7.45 (t, 1H, J=7.8Hz), 7.40 (t, 2H, J=7.9Hz), 7.31 (d, 1H, J=7.2Hz), 5.41 (d, 1H, J=6.0Hz), 4.95 (d, 1H, J=6.0Hz), 4.81 (d, 1H, J=5.4Hz), 4.75 (d, 1H, J=5.4Hz), 3.93 (s, 3H), 2.63 (m, 1H, J=6.9Hz), 2.19 (s, 3H), 1.18, 1.13 (2d, 6H, J=6.9Hz) ppm..
3. a preparation method for iridium metal complex as claimed in claim 1, is characterized in that, comprises the following steps:
Step one, by m-hydroxybenzaldehyde and acetone mixing mix after, mix with salt of wormwood mixing again and obtain light yellow transparent solution, after heated and stirred backflow certain hour, described light yellow transparent solution is mixed with methyl-sulfate, filter after reaction certain hour and obtain filtrate, after filtrate is spin-dried for and deionized water be mixed to get the first mixed solution, extraction agent is used to be extracted liquid layer to the extraction that the first mixed solution carries out more than 3 times, be spin-dried for after extraction liquid layer and the mixing of a certain amount of siccative, obtain NSC 43794, structural formula is as follows:
Step 2, gained NSC 43794, dehydrated alcohol and 4-phenyl-3-thiosemicarbazide to be mixed, under certain temperature after return stirring for some time, obtain micro-purple solution, described micro-purple solution is concentrated into a certain amount of after, mix with ethanol and normal hexane, separate out white crystal, be NSC 43794 contracting 4-phenyl-3-thiosemicarbazide, structural formula is as follows:
Step 3, described NSC 43794 contracting 4-methyl-3-thiosemicarbazide and dichloro (pentamethylcyclopentadiene base) are closed iridium (III) dimer and CH
2cl
2be mixed to get the second mixed solution, after stirring for some time under certain temperature, by described second mixed solution underpressure distillation to certain volume, leave standstill and separate out orange solids, namely product one chlorine one NSC 43794 contracting 4-phenyl-3-thiosemicarbazide First Five-Year Plan methyl cyclopentadienyl of the present invention closes iridium (III).
4. the preparation method of iridium metal complex as claimed in claim 3, it is characterized in that, in step one, each amounts of components used is respectively: m-hydroxybenzaldehyde 4-10g, acetone 5-20ml, salt of wormwood 2-5g, methyl-sulfate 2-10ml, deionized water 2-5ml, extraction agent 2-10m and siccative 5-20g, described heated and stirred reflux temperature is 30-50 DEG C, time is 5-20 minute, described light yellow transparent solution and methyl-sulfate hybrid reaction time are 10-15h, wherein, described alr mode is magnetic agitation, the concentration of described acetone is 90-100%, extraction agent is the ethyl acetate of concentration 90-100%, siccative is Anhydrous potassium carbonate.
5. the preparation method of iridium metal complex as claimed in claim 3, it is characterized in that, in step 2, each amounts of components used is respectively: NSC 43794 2-5g, dehydrated alcohol 5-20ml, 4-phenyl-3-thiosemicarbazide 1-5g, ethanol 2-10ml and normal hexane 2-10ml, the temperature of described return stirring is 50-70 DEG C, time is 3-6h, the concentrated amount of described micro-purple solution is 1-3ml, wherein, the concentration of described ethanol is 90-100%, the concentration of normal hexane is 90-100%, described micro-purple solution condensing mode is for being spin-dried for, described alr mode is magnetic agitation.
6. the preparation method of iridium metal complex as claimed in claim 3, it is characterized in that, churning time described in step 3 is 5-8 hour, whipping temp is 15-35 DEG C, each amounts of components used is respectively: NSC 43794 contracting 4-methyl-3-thiosemicarbazide 15-30mg, dichloro (pentamethylcyclopentadiene base) closes iridium (III) dimer 20-40mg and CH
2cl
25-10ml, the temperature of described stirring is 10-40 DEG C, and the time is 3-8h, and described distillation volume is 1-3ml, wherein, described CH
2cl
2concentration 90-100%, alr mode is magnetic agitation.
7. a purposes for iridium metal complex as claimed in claim 1, is characterized in that, described iridium metal complex is for the preparation of the application of Therapeutic cancer and anti-parasite medicine.
8. a purposes for iridium metal complex as claimed in claim 7, is characterized in that, described iridium metal complex can be made into the form of injection, tablet, pill, capsule, suspension agent or emulsion.
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| CN105251055A (en) * | 2015-11-17 | 2016-01-20 | 广西中医药大学 | Method for improving antibacterial and anticancer performance of titanium dioxide nanotube by means of iridium complex |
| CN105288723A (en) * | 2015-11-17 | 2016-02-03 | 广西中医药大学 | Method for treating titanium dioxide nano-tubes by using iridium coordination compound |
| CN105327391A (en) * | 2015-11-17 | 2016-02-17 | 广西中医药大学 | Method for preparing anti-bacterial and anti-cancer titanium dioxide nanotube from iridium complex |
| CN105396174A (en) * | 2015-11-20 | 2016-03-16 | 广西中医药大学 | Method for preparing titanium dioxide nanotube with antibacterial and anti-cancer properties |
| CN105420718A (en) * | 2015-11-17 | 2016-03-23 | 广西中医药大学 | Iridium complex modified stainless steel material, and preparation method and application thereof |
| CN105457087A (en) * | 2015-11-17 | 2016-04-06 | 广西中医药大学 | Titanium metal material modified by iridium complexes and preparation method and application thereof |
| CN106748939A (en) * | 2016-11-29 | 2017-05-31 | 中国科学院海洋研究所 | The new bromine phenol thiosemicarbazide compound of one class and its preparation and medicine and purposes |
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| CN105420718B (en) * | 2015-11-17 | 2018-09-04 | 广西中医药大学 | Stainless steel material of complex of iridium modification and preparation method thereof and purposes |
| CN105420718A (en) * | 2015-11-17 | 2016-03-23 | 广西中医药大学 | Iridium complex modified stainless steel material, and preparation method and application thereof |
| CN105457087A (en) * | 2015-11-17 | 2016-04-06 | 广西中医药大学 | Titanium metal material modified by iridium complexes and preparation method and application thereof |
| CN105457087B (en) * | 2015-11-17 | 2018-06-29 | 广西中医药大学 | Titanium metal material of complex of iridium modification and its preparation method and application |
| CN105396174B (en) * | 2015-11-20 | 2018-06-29 | 广西中医药大学 | A kind of method for preparing the titania nanotube with antibacterial anti-cancer properties |
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