CN102731561A - Dibutyltin coordination compound, preparation method of dibutyltin coordination compound and application of ibutyltin coordination compound - Google Patents
Dibutyltin coordination compound, preparation method of dibutyltin coordination compound and application of ibutyltin coordination compound Download PDFInfo
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- CN102731561A CN102731561A CN2012102345943A CN201210234594A CN102731561A CN 102731561 A CN102731561 A CN 102731561A CN 2012102345943 A CN2012102345943 A CN 2012102345943A CN 201210234594 A CN201210234594 A CN 201210234594A CN 102731561 A CN102731561 A CN 102731561A
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- JSWATIQCJKVRBF-UHFFFAOYSA-N CCOCC(C(C)Oc1ccccc1)=O Chemical compound CCOCC(C(C)Oc1ccccc1)=O JSWATIQCJKVRBF-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a dibutyltin coordination compound, a preparation method of the dibutyltin coordination compound and application of the dibutyltin coordination compound. The structural formula of the dibutyltin coordination compound is shown in the specification. The preparation method comprises the following steps of: adding 1mmol of 2-phenoxypropionic acid, 0.1-1.5mmol of potassium hydroxide, 0.5-1.5mmol of dibutyltin dichloride and 20-30ml of methanol into a container, stirring and refluxing for 6-7 hours at the room temperature, and then carrying out rotary evaporation to obtain a faint yellow solid; and recrystallizing by using dichloromethane-petroleum ether to obtain faint yellow transparent crystal, i.e. the dibutyltin coordination compound, wherein the volume ratio of the dichloromethane to the petroleum ether is 1:1-2:1. The application of the dibutyltin coordination compound lies in preparing medicaments for treating human ileocecum adenocarcinoma, human lung adenocarcinoma and human colon cancer. The organic dibutyltin coordination compound has the characteristics of high anti-cancer activity, good fat solubility, low cost, simple preparation method, and the like and provides a new approach for developing anti-cancer medicaments.
Description
Technical field
The present invention relates to a kind of dibutyl tin coordination compound, and preparation method thereof, and the application of this compound in the preparation cancer therapy drug.
Background technology
The research of organo-tin compound can be traced back to 1840s the earliest; But the real prosperity of organotin chemistry starts from the eighties in 20th century; People were in research and screening process to the metal cancer therapy drug at that time; Find that some dialkyl tin compounds have anti-tumor activity (Crowe, the A.J. higher than cis-platinum; Smith, P.J.; Atassi.G., Chem.Biol.Interact., 1980,32,171).After this, Along with people's deepens continuously to the research of organo-tin compound, and the research field and the range of application of organotin chemistry also constantly enlarge thereupon.
Summary of the invention
To above-mentioned prior art, the invention provides a kind of new organotin coordination compound, and the preparation method and the application thereof of this compound are provided.
A kind of dibutyl tin coordination compound, structural formula is following:
Wherein, Me representes methyl, and n-Bu representes normal-butyl.
A kind of preparation method of organotin coordination compound: in container, add the 2-phenoxy propionic acid of 1mmol, the Pottasium Hydroxide of 0.5～1.5mmol, the dibutyl tin dichloride of 0.5～1.5mmol, the methyl alcohol of 20～30ml; Under the room temperature stirring and refluxing 6-7 hour; Rotary evaporation obtains faint yellow solid; With methylene dichloride-sherwood oil recrystallization, obtain faint yellow transparent crystals, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 1:1～2:1.Reaction formula is:
The application of said dibutyl tin coordination compound in the medicine of preparation treatment people ileocecum gland cancer, human lung adenocarcinoma, human colon carcinoma.
Dibutyl tin coordination compound molecular formula of the present invention is C
68H
104O
14Sn
4Molecular weight is 1620.36, has higher anti-cancer activity, can its medicine for feedstock production treatment people ileocecum gland cancer, human lung adenocarcinoma, human colon carcinoma.With anticancer the comparing of platinum class of generally using at present, organotin coordination compound of the present invention has antitumour activity height, fat-soluble good, characteristics such as cost is low, the preparation method is simple, for the exploitation cancer therapy drug provides new way.
Embodiment
Below in conjunction with embodiment the present invention is further described:
Embodiment 1: preparation dibutyl tin coordination compound: in flask, add the 2-phenoxy propionic acid of 1.0mmol, the Pottasium Hydroxide of 1.0mmol, the dibutyl tin dichloride of 1.0mmol; The methyl alcohol of 20ml; At room temperature stirred 7 hours, rotary evaporation obtains faint yellow solid; With methylene dichloride-sherwood oil recrystallization, obtain faint yellow transparent crystals, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 1:1.Productive rate 76%, fusing point 112-114 ℃.
Through IR spectroscopy and nuclear magnetic resonance spectroscopy, the result is following:
Ir spectra (KBr, cm
-1): v
As(C=O) 1639,1600, v
s(C-O) 1379,1237; V (Sn-O-Sn) 688,639, v (Sn-O) 484,421.
1H nuclear-magnetism (CDCl
3, ppm): δ 6.86-7.30 (m, 20H, C
6H
5O); 4.77 (q, 4H, CH), 1.63 (d, 12H, CH
3-CH).
13C nuclear-magnetism (CDCl
3, ppm): δ 172.86 (C=O); 157.80,129.81,129.74,121.82,115.36,115.19 (C
6H
5O); 52.60 (CH); 18.76 (CH
3).
Ultimate analysis: calculated value C
68H
104O
14Sn
4: C, 50.40; H, 6.47; O, 13.82; Measured value C, 50.46; H, 6.55; O, 13.75%.
Embodiment 2: preparation dibutyl tin coordination compound: in flask, add the 2-phenoxy propionic acid of 1.0mmol, the Pottasium Hydroxide of 1.2mmol, the dibutyl tin dichloride of 1.5mmol; The methyl alcohol of 30ml; At room temperature stirred 7 hours, rotary evaporation obtains faint yellow solid; With methylene dichloride-sherwood oil recrystallization, obtain faint yellow transparent crystals, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 2:1.Productive rate 71%, fusing point 112-114 ℃.
Embodiment 3: preparation dibutyl tin coordination compound: in flask, add the 2-phenoxy propionic acid of 1.0mmol, the Pottasium Hydroxide of 1.5mmol, the dibutyl tin dichloride of 1.0mmol; The methyl alcohol of 30ml; At room temperature stirred 6 hours, rotary evaporation obtains faint yellow solid; With methylene dichloride-sherwood oil recrystallization, obtain faint yellow transparent crystals, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 2:1.Productive rate 69%, fusing point 112-114 ℃.
Test Example: dibutyl tin coordination compound of the present invention, its external antitumour activity is measured through the MTT experimental technique and is realized that its principle is: 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; Can yellow MTT be reduced into insoluble hepatic Formazan, dead cell does not have this enzyme, and MTT is not reduced; Behind DMSO dissolving Formazan; Available ELIASA is measured the optical density(OD) of characteristic wavelength, carries out relevant data and handles, and reaches a conclusion.
With the MTT analytical method people's ileocecum gland cancer HCT-8 cell strain, human lung adenocarcinoma A549 cell strain, human colon carcinoma HCT-116 cell strain are analyzed, measured its IC
50Value, the result sees table 1, conclusion is: can know according to data in the table, cancer therapy drug of the present invention, very high to the external activity of people's ileocecum gland cancer, adenocarcinoma of lung, can be used as the candidate compound of cancer therapy drug.
Table 1 organotin coordination compound cancer therapy drug external activity test data
| People's enteraden cancer | Human lung adenocarcinoma | Human colon carcinoma | |
| Cell strain | HCT-8 | A549 | HCT-116 |
| Sample IC 50（μg/mL） | 0.175±0.0008 | 0.823±0.0009 | 0.114±0.0006 |
| Cis-platinum IC 50（μg/mL） | 1.26 | 1.91 | 2.04 |
Claims (4)
1. dibutyl tin coordination compound, it is characterized in that: structural formula is following:
Wherein, Me=CH
3; N-Bu=CH
2CH
2CH
2CH
3
2. the preparation method of the described a kind of organotin coordination compound of claim 1; It is characterized in that: step is: in container, add the 2-phenoxy propionic acid of 1mmol, the Pottasium Hydroxide of 0.5～1.5mmol, the dibutyl tin dichloride of 0.5～1.5mmol, the methyl alcohol of 20～30ml; Stirring and refluxing 6-7 hour; Evaporation obtains faint yellow solid; With methylene dichloride-sherwood oil recrystallization, obtain faint yellow transparent crystals, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 1:1～2:1.
3. preparation method as claimed in claim 2; It is characterized in that; Said step is: in flask, add the 2-phenoxy propionic acid of 1.0mmol, the Pottasium Hydroxide of 1.0mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 20ml at room temperature stirred 7 hours; Rotary evaporation obtains faint yellow solid; With methylene dichloride-sherwood oil recrystallization, obtain faint yellow transparent crystals, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 1:1.
4. the application of the described dibutyl tin coordination compound of claim 1 in the medicine of preparation treatment people ileocecum gland cancer, human lung adenocarcinoma, human colon carcinoma.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1238336A (en) * | 1999-06-02 | 1999-12-15 | 山西大学 | Dibutyl tin compound of polynuclear heterocarboxyl acids and its synthesis |
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2012
- 2012-07-09 CN CN2012102345943A patent/CN102731561A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1238336A (en) * | 1999-06-02 | 1999-12-15 | 山西大学 | Dibutyl tin compound of polynuclear heterocarboxyl acids and its synthesis |
Non-Patent Citations (1)
| Title |
|---|
| 闫文华等: "《新型二正丁基锡(IV)羧酸酯的合成、晶体结构及杀菌活性研究》", 《化学通报》 * |
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