CN103044482B - A kind of dibutyl tin coordination compound and preparation method thereof and application - Google Patents
A kind of dibutyl tin coordination compound and preparation method thereof and application Download PDFInfo
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- CN103044482B CN103044482B CN201310023060.0A CN201310023060A CN103044482B CN 103044482 B CN103044482 B CN 103044482B CN 201310023060 A CN201310023060 A CN 201310023060A CN 103044482 B CN103044482 B CN 103044482B
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Abstract
The invention discloses a kind of dibutyl tin coordination compound and preparation method thereof and application, structural formula is as follows, preparation method is: in reaction vessel, add 1.0mmol 2-O-phthalic base imido grpup propionic acid, the potassium hydroxide of 1.0 ~ 1.5mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 20 ~ 30mL, stirred at ambient temperature backflow 5 ~ 6 hours, rotary evaporation, obtains faint yellow solid; Use dichloromethane-petroleum ether recrystallization, obtain pale yellow transparent crystal, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 2:1 ~ 5:1.Compared with anticancer with the platinum class generally used at present, organotin coordination compound of the present invention has high, fat-soluble good, the feature such as cost is low, preparation method is simple of antitumour activity, for exploitation cancer therapy drug provides new way.
Description
Technical field
The present invention relates to a kind of dibutyl tin coordination compound, and preparation method thereof, and this compound is preparing the application in cancer therapy drug.
Background technology
The research of organo-tin compound can trace back to 1840s the earliest, but the real prosperity of organotin chemistry starts from the eighties in 20th century, people were in the research of Metal Anticancer Drug and screening process 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 deepen continuously to the research of organo-tin compound, research field and the range of application of organotin chemistry also constantly expand thereupon.
Summary of the invention
The object of the invention is, for overcoming above-mentioned the deficiencies in the prior art, to provide a kind of new organotin coordination compound, and provide preparation method and the application thereof of this compound.
For achieving the above object, the present invention adopts following technical proposals:
A kind of dibutyl tin coordination compound, structural formula is as follows:
Wherein, n-Bu represents normal-butyl.
A kind of preparation method of organotin coordination compound: the 2-O-phthalic base imido grpup propionic acid, the potassium hydroxide of 1.0 ~ 1.5mmol, the dibutyl tin dichloride of 1mmol, the methyl alcohol of 20 ~ 30mL that add 1.0mmol in reaction vessel, stirred at ambient temperature 5 ~ 6 hours, rotary evaporation, obtains faint yellow solid; Use dichloromethane-petroleum ether recrystallization, obtain pale yellow transparent crystal, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 2:1 ~ 5:1.
Reaction formula is:
The application of described dibutyl tin coordination compound in preparation treatment human colon carcinoma, adenocarcinoma of lung, adenocarcinoma of colon and leukemic medicine.
The invention has the beneficial effects as follows, dibutyl tin complex molecules formula of the present invention is C
30h
34n
2o
8sn; Molecular weight is 669.28, has higher antitumour activity, can it be raw material preparation treatment human colon carcinoma, adenocarcinoma of lung, adenocarcinoma of colon and leukemic medicine.Compared with anticancer with the platinum class generally used at present, organotin coordination compound of the present invention has high, fat-soluble good, the feature such as cost is low, preparation method is simple of antitumour activity, for exploitation cancer therapy drug provides new way.
Embodiment
Below in conjunction with embodiment, the present invention will be further elaborated, should be noted that following explanation is only to explain the present invention, not limiting its content.
Embodiment 1:
Prepare dibutyl tin coordination compound: in flask, add 1.0mmol 2-O-phthalic base imido grpup propionic acid, the potassium hydroxide of 1.5mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 30mL, at room temperature stir 6 hours, rotary evaporation, obtains faint yellow solid; Use dichloromethane-petroleum ether recrystallization, obtain pale yellow transparent crystal, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 5:1.Productive rate 86%, fusing point 113-116 DEG C.
Through Infrared spectroscopy and nuclear magnetic resonance spectroscopy, result is as follows:
Infrared spectra (KBr, cm
-1): ν
as(C=O) 1605.3; v
s(C-O) 1394.8; ν (Sn-O) 546,478.
1h nuclear-magnetism (CDCl
3, ppm): δ 7.69-7.84 (m, 8H, Ph); 4.99 (q, 2H, CH), 1.69 (d, 6H, CH
3-CH).
13c nuclear-magnetism (CDCl
3, ppm): δ 179.43 (C=O); 167.46,134.22,134.16,132.30,123.58,116.06(Ph); 47.81 (CH); 15.96 (CH
3).
Ultimate analysis: calculated value C
30h
34n
2o
8sn:C, 53.83; H, 5.12; N, 19.12 measured value C, 53.86; H, 5.16; N, 19.08%.
Embodiment 2:
Prepare dibutyl tin coordination compound: in flask, add 1.0mmol 2-O-phthalic base imido grpup propionic acid, the potassium hydroxide of 1.2mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 30mL, at room temperature stir 6 hours, rotary evaporation, obtains faint yellow solid; Use dichloromethane-petroleum ether recrystallization, obtain pale yellow transparent crystal, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 3:1.Productive rate 80%, fusing point 113-116 DEG C.
Embodiment 3:
Prepare dibutyl tin coordination compound: in flask, add 1.0mmol 2-O-phthalic base imido grpup propionic acid, the potassium hydroxide of 1.0mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 20mL, at room temperature stir 5 hours, rotary evaporation, obtains faint yellow solid; Use dichloromethane-petroleum ether recrystallization, obtain pale yellow transparent crystal, be organotin coordination compound; Wherein, the volume ratio of methylene dichloride and sherwood oil is 2:1.Productive rate 76%, fusing point 113-116 DEG C.
Test example:
Dibutyl tin coordination compound of the present invention, its Anticancer Activity in vitro is measured and is realized by MTT experiment method, its principle is: reduce exogenous MTT(3-(4 with metabolism, 5-dimethylthiazol-2-yl)-2, 5-diphenyl terrazoliumbromide) based on, the desaturase relevant to NADP is there is in viable cell plastosome, yellow MTT can be reduced into insoluble bluish voilet crystallization first a ceremonial jade-ladle, used in libation (Formazan), dead cell is without this enzyme, MTT is not reduced, after dissolving Formazan with DMSO, available microplate reader measures the optical density(OD) at characteristic wavelength (490nm wavelength) place, carry out relevant data process, reach a conclusion.The method can reflect viable cell quantity indirectly.Within the scope of certain cell count, the amount that MTT crystallization is formed is directly proportional to cell count.The method has been widely used in Activity determination, large-scale screening anti-tumor medicine, cell toxicity test and the tumor radiosensitivity mensuration etc. of some biologically active factorss.
With MTT analytical method, human colon carcinoma HCT-116 cell strain, lung adenocarcinoma A549 cell line, adenocarcinoma of colon Caco-2 cell strain and leukemia HL-60 cell strain are analyzed, measure its IC
50value, the results are shown in Table 1, conclusion is: according to data in table, and cancer therapy drug of the present invention is very high to human colon carcinoma, adenocarcinoma of lung, adenocarcinoma of colon and leukemic external activity, can be used as the candidate compound of cancer therapy drug.
Table 1 organotin coordination compound cancer therapy drug external activity test data
| Human colon carcinoma | Human lung adenocarcinoma | Adenocarcinoma of colon | Leukemia | |
| Sample IC 50（μg/mL） | 0.342±0.009 | 6.27±0.01 | 0.143±0.006 | 0.138±0.002 |
| Cell strain | HCT-116 | A549 | Caco-2 | HL-60 |
Although above-mentioned, the specific embodiment of the present invention is described; but not limiting the scope of the invention; on the basis of technical scheme of the present invention, those skilled in the art do not need to pay various amendment or distortion that creative work can make still within protection scope of the present invention.
Claims (1)
1. the application of dibutyl tin coordination compound in preparation treatment human colon carcinoma, adenocarcinoma of lung, adenocarcinoma of colon and leukemic medicine, it is characterized in that, its structural formula is as follows:
Wherein, n-Bu represents normal-butyl.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1100804B1 (en) * | 1998-07-29 | 2002-10-09 | Pharmachemie B.V. | Tin polyoxaalkanecarboxylates and compositions containing them |
| CN102127106A (en) * | 2010-12-30 | 2011-07-20 | 聊城大学 | Dichlorodiphenyl-stannane complex and preparation method and application thereof |
| CN102584888A (en) * | 2011-12-25 | 2012-07-18 | 聊城大学 | 2-carboxyl benzamido thiourea trimethyltin compound, preparation method and application |
-
2013
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1100804B1 (en) * | 1998-07-29 | 2002-10-09 | Pharmachemie B.V. | Tin polyoxaalkanecarboxylates and compositions containing them |
| CN102127106A (en) * | 2010-12-30 | 2011-07-20 | 聊城大学 | Dichlorodiphenyl-stannane complex and preparation method and application thereof |
| CN102584888A (en) * | 2011-12-25 | 2012-07-18 | 聊城大学 | 2-carboxyl benzamido thiourea trimethyltin compound, preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| Anurag Joshl等.Di-n-butyltin(IV) Complexes Derived from Heterocyclic β-diketones and N-Phthaloyl Amino Acids: Preparation,Biological Evaluation, Structural Elucidation Based upon Spectral [IR, NMR (1H,13C, 19F and 119Sn)] Studies.《Bioionorganic Chmistry and Applications》.2005,第3卷(第3-4期),第201-215页. * |
| Synthesis of novel bioactive phthalimido-4-methyl pentanoateorganotin(IV) esters with spectroscopic investigation;Muhammad Ashfaq;《Journal of Organometallic Chemistry》;20060228;第691卷(第8期);第1803页左栏第1段第3-6行，1804页左栏第1段，方程式（1）、（2），第1806页左栏图4，第1807页左栏3.3.1节 * |
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