CN103044482A - Dibutyltin coordination compound and preparation method and application thereof - Google Patents
Dibutyltin coordination compound and preparation method and application thereof Download PDFInfo
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- CN103044482A CN103044482A CN2013100230600A CN201310023060A CN103044482A CN 103044482 A CN103044482 A CN 103044482A CN 2013100230600 A CN2013100230600 A CN 2013100230600A CN 201310023060 A CN201310023060 A CN 201310023060A CN 103044482 A CN103044482 A CN 103044482A
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Abstract
The invention discloses a dibutyltin coordination compound and a preparation method and application thereof. The structural formula is shown in the specification, wherein n-Bu represents n-butyl. The preparation method comprises the following steps of: adding 1.0mmol of 2-phthalic iminopropionic acid, 1.0-1.5mmol of potassium hydroxide, 1.0mmol of dibutyltin dichloride and 20-30mL of methanol into a reaction container; stirring for backflow for 5-6 hours at room temperature; performing rotary evaporation to obtain a slightly yellow solid; and recrystallizing with dichloromethane-petroleum ether to obtain a slightly yellow transparent crystal which is an organic tin coordination compound, wherein the volume ratio of dichloromethane to petroleum ether is (2:1)-(5:1). Compared with the common platinum anti-cancer compound, the organic tin coordination compound disclosed by the invention has the characteristics of high anti-cancer activity, good lipid solubility, low cost, simple preparation method and the like, and provides a new means of developing an anti-cancer drug.
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 Metal Anticancer 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 deepen continuously to the research of organo-tin compound, the research field of organotin chemistry and range of application also constantly enlarge thereupon.
Summary of the invention
The objective of the invention is provides a kind of new organotin coordination compound for overcoming above-mentioned the deficiencies in the prior art, and preparation method and the application thereof of this compound are provided.
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: in reaction vessel, add the 2-O-phthalic base imido grpup propionic acid of 1.0mmol, the potassium hydroxide of 1.0 ~ 1.5mmol, the dibutyl tin dichloride of 1mmol, the methyl alcohol of 20 ~ 30mL, stirred under the room temperature 5 ~ 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 ~ 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 coordination compound molecular 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.With anticancer the comparing of platinum class of generally using at present, organotin coordination compound of the present invention has high, 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 will be further elaborated below in conjunction with embodiment, should be noted that following explanation only is in order to explain the present invention, its content not to be limited.
Embodiment 1:
Preparation dibutyl tin coordination compound: in flask, add the 2-O-phthalic base imido grpup propionic acid of 1.0mmol, the potassium 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 5:1.Productive rate 86%, fusing point 113-116 ℃.
Through Infrared spectroscopy and nuclear magnetic resonance spectroscopy, the 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:
Preparation dibutyl tin coordination compound: in flask, add the 2-O-phthalic base imido grpup propionic acid of 1.0mmol, the potassium hydroxide of 1.2mmol, 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 3:1.Productive rate 80%, fusing point 113-116 ℃.
Embodiment 3:
Preparation dibutyl tin coordination compound: in flask, add the 2-O-phthalic base imido grpup propionic acid of 1.0mmol, the potassium hydroxide of 1.0mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 20mL, at room temperature stirred 5 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 76%, fusing point 113-116 ℃.
Test example:
Dibutyl tin coordination compound of the present invention, its Anticancer Activity in vitro is measured and is realized by the MTT experimental technique, its principle is: reduce exogenous MTT(3-(4 with metabolism, 5-dimethylthiazol-2-yl)-2,5-diphenyl terrazolium bromide) is the basis, there be the desaturase relevant with NADP in the 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, and behind DMSO dissolving Formazan, available microplate reader is measured the optical density(OD) that characteristic wavelength (490nm wavelength) is located, carry out relevant data and process, reach a conclusion.The method can reflect viable cell quantity indirectly.In certain cell count scope, the amount that the MTT crystallization forms is directly proportional with cell count.The method has been widely used in the activity detection of some biologically active factorss, large-scale screening anti-tumor medicine, cell toxicity test and tumor radiosensitivity mensuration etc.
With the 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, measured its IC
50Value the results are shown in Table 1, and conclusion is: according to data in the table as can be known, cancer therapy drug of the present invention, 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 be 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 modifications that creative work can make or distortion still in protection scope of the present invention.
Claims (3)
1. a dibutyl tin coordination compound is characterized in that, structural formula is as follows:
Wherein, n-Bu represents normal-butyl.
2. the preparation method of a kind of dibutyl tin coordination compound claimed in claim 1 is characterized in that, step is as follows:
Add the 2-O-phthalic base imido grpup propionic acid of 1.0mmol, the potassium hydroxide of 1.0 ~ 1.5mmol, the dibutyl tin dichloride of 1.0mmol, the methyl alcohol of 20 ~ 30mL in reaction vessel, stirring and refluxing is 5 ~ 6 hours under the room temperature, and 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 ~ 5:1.
3. the application of dibutyl tin coordination compound claimed in claim 1 in preparation treatment human colon carcinoma, adenocarcinoma of lung, adenocarcinoma of colon and leukemic medicine.
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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
- 2013-01-22 CN CN201310023060.0A patent/CN103044482B/en not_active Expired - Fee Related
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》 * |
| MUHAMMAD ASHFAQ: "Synthesis of novel bioactive phthalimido-4-methyl pentanoateorganotin(IV) esters with spectroscopic investigation", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
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