CN107602606A - A kind of three (adjacent bromobenzyl) tin salicylate complexs and preparation method and application - Google Patents
A kind of three (adjacent bromobenzyl) tin salicylate complexs and preparation method and application Download PDFInfo
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- CN107602606A CN107602606A CN201710842058.4A CN201710842058A CN107602606A CN 107602606 A CN107602606 A CN 107602606A CN 201710842058 A CN201710842058 A CN 201710842058A CN 107602606 A CN107602606 A CN 107602606A
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Abstract
A kind of three (adjacent bromobenzyl) tin salicylate complex disclosed by the invention and preparation method and application, it is the complex of following structure formula (I).The invention also discloses three (adjacent bromobenzyl) tin salicylate complex preparation methods and the application in treating cancer medicine is prepared.
Description
Technical field
The present invention relates to a kind of three (adjacent bromobenzyl) tin salicylate complexs, and preparation method thereof, and three (the adjacent bromine
Benzyl) application of the tin salicylate complex in antineoplastic is prepared.
Background technology
Organotin is a kind of metallo-organic compound containing Sn-C keys, has higher bioactivity, is sterilizing, killing
The fields such as worm, cancer therapy drug preparation have a wide range of applications.Existing research shows that the alkyl R in organotin is to determine
The principal element of compound anti-cancering activity height, e.g., the active anticancer of cyclohexyl, normal-butyl and phenyl tin compound are stronger, second
Base takes second place, and methyl is then almost without active anticancer.The structure of part is to the active anticancer of complex and the wide spectrum of killing cancer cell
Property also plays an important role, it is demonstrated experimentally that the bioactivity of organotin carboxylate complex is often than corresponding organotin
Compound is high.
Chinese patent CN101402650B disclose a kind of dibutyl tin and quinolinecarboxylic acid complex prepare treatment stomach cancer,
Applied in the medicine of nasopharyngeal carcinoma, human liver cancer or leukaemia.
Chinese patent CN101434616B discloses a kind of dibutyl tin Schiff base complex and is preparing treatment stomach cancer, nose
Applied in the medicine of pharynx cancer, human liver cancer or leukaemia.
Chinese patent CN103396437B discloses double (Tricyclohexyltin) carboxylates and is preparing treatment cervical carcinoma, mammary gland
Cancer, liver cancer, colon cancer and lung cancer medicine in apply.
It is that the experiment proved that the material with active anticancer based on organotin carboxylate's esters compound, present invention selection three
(adjacent bromobenzyl) stannic chloride, with part salicylic acid, reacts under certain condition, and synthesis has obtained that (human lung cancer is thin to NCI-H460
Born of the same parents), the stronger compound of A549 (human lung carcinoma cell), MCF7 (people's breast adenocarcinoma cell) inhibitory activity, to develop anticarcinogen
Thing provides new way.
The content of the invention
In view of the above-mentioned problems of the prior art, the first object of the present invention there is provided a kind of three (adjacent bromobenzyl) tin
Salicylate complex.
The second object of the present invention is to provide the preparation method of above-mentioned three (adjacent bromobenzyl) tin salicylate complexs.
The 3rd mesh of the present invention is to provide above-mentioned three (adjacent bromobenzyl) tin salicylate complexs in cancer therapy drug is prepared
Application.
As one kind three (adjacent bromobenzyl) tin salicylate complex of first aspect present invention, it is following structural formula
(I) complex：
Three (adjacent bromobenzyl) the tin salicylate complexs of the present invention are analyzed through elementary analysis and x-ray crystal structure, knot
Fruit is as follows：
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
FT-IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-
C),428v(Sn-O)。
Three (adjacent bromobenzyl) the tin salicylate complexs of the present invention are crystal structure, its crystallographic data：Crystal belongs to three
Oblique system, space groupA=1.12298 (11) nm, b=1.12514 (11) nm, c=1.13003 (11) nm, α=
104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=2, V=1.3637 (2) nm3, Dc=
1.865Mg·m-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of 27.60 ° of ＜ θ ＜, crystalline size：0.23x
0.21x 0.20mm, R=0.0369, wR=0.0751.
Three (adjacent bromobenzyl) tin salicylate complexs of the present invention are structurally characterized in that：Center tin and coordination in molecule
Atomic building four-coordination distortion tetrahedral configuration.
As the preparation method of one kind three (adjacent bromobenzyl) tin salicylate complex of second aspect of the present invention, reacting
Salicylic acid, three (adjacent bromobenzyl) stannic chloride, triethylamine and etoh solvents are sequentially added in container in order, are 50~65 in temperature
8~24h is reacted under conditions of DEG C；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains water white transparency
Crystal, as three (adjacent bromobenzyl) tin salicylate complexs.
In a preferred embodiment of the invention, the salicylic acid, three (adjacent bromobenzyl) stannic chlorides, the material of triethylamine
Amount ratio be 1:1~1.05:1.
In a preferred embodiment of the invention, the etoh solvent dosage is every mM three (adjacent bromobenzyl) chlorination
Tin adds 20~35 milliliters.
One kind three (adjacent bromobenzyl) tin salicylate complex as third aspect present invention is in cancer therapy drug is prepared
Application.
Applicant has carried out anti tumor activity in vitro to above-mentioned complex and has confirmed research, confirms that the complex has necessarily
Anti-tumor biological, that is to say, that the purposes of above-mentioned complex is the application in antineoplastic is prepared, specifically
It is the application in anti-human lung-cancer medicament, human breast carcinoma medicine is prepared.
Three (adjacent bromobenzyl) the tin salicylate complexs of the present invention are shown well to human lung cancer medicine, human breast carcinoma etc.
Active anticancer, can using its as raw material prepare anti-lung cancer, anti-breast cancer medicines.With the platinum-containing anticancer drug phase being commonly used
Than of the invention three (adjacent bromobenzyl) tin salicylate complexs have the spies such as active anticancer is high, cost is low, preparation method is simple
Point, new way is provided for exploitation cancer therapy drug.
Brief description of the drawings
Fig. 1 is the crystal molecular structure figure of three (adjacent bromobenzyl) tin salicylate complexs.
Fig. 2 is the IR spectrograms of three (adjacent bromobenzyl) tin salicylate complexs.
Embodiment
The present invention is further described by following examples, but should be noted that the scope of the present invention is not implemented by these
Any restrictions of example.
Embodiment 1：
The preparation of three (adjacent bromobenzyl) tin salicylate complexs：
Sequentially add salicylic acid 0.1383g (1mmol), three (adjacent bromobenzyl) chlorinations in order in 100ml round-bottomed flasks
Tin 0.6645g (1mmol), triethylamine 0.1014g (1mmol), etoh solvent 20mL are anti-under conditions of being 50~65 DEG C in temperature
Answer 8h；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains colourless transparent crystal, as three (adjacent bromines
Benzyl) tin salicylate complex.Yield：65%, fusing point：120-122℃.
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-C),
428v(Sn-O)。
Its crystallographic data：Crystal category anorthic system, space groupB=1.12514
(11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=
2, V=1.3637 (2) nm3, Dc=1.865Mgm-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of ＜ θ ＜
27.60 °, crystalline size：0.23x 0.21x 0.20mm, R=0.0369, wR=0.0751.
Embodiment 2：
The preparation of three (adjacent bromobenzyl) tin salicylate complexs：
Sequentially add salicylic acid 0.1387g (1mmol), three (adjacent bromobenzyl) chlorinations in order in 100ml round-bottomed flasks
Tin 0.6641g (1mmol), triethylamine 0.1019g (1mmol), etoh solvent 35mL are anti-under conditions of being 50~65 DEG C in temperature
Answer 8h；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains colourless transparent crystal, as three (adjacent bromines
Benzyl) tin salicylate complex.Yield：67%, fusing point：120-122℃.
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-C),
428v(Sn-O)。
Its crystallographic data：Crystal category anorthic system, space groupB=1.12514
(11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=
2, V=1.3637 (2) nm3, Dc=1.865Mgm-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of ＜ θ ＜
27.60 °, crystalline size：0.23x 0.21x 0.20mm, R=0.0369, wR=0.0751.
Embodiment 3：
The preparation of three (adjacent bromobenzyl) tin salicylate complexs：
Sequentially add salicylic acid 0.1384g (1mmol), three (adjacent bromobenzyl) chlorinations in order in 100ml round-bottomed flasks
Tin 0.6645g (1mmol), triethylamine 0.1016g (1mmol), etoh solvent 35mL are anti-under conditions of being 50~65 DEG C in temperature
Answer 16h；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains colourless transparent crystal, as three (adjacent bromines
Benzyl) tin salicylate complex.Yield：70%, fusing point：120-122℃.
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-C),
428v(Sn-O)。
Its crystallographic data：Crystal category anorthic system, space groupB=1.12514
(11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=
2, V=1.3637 (2) nm3, Dc=1.865Mgm-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of ＜ θ ＜
27.60 °, crystalline size：0.23x 0.21x 0.20mm, R=0.0369, wR=0.0751.
Embodiment 4：
The preparation of three (adjacent bromobenzyl) tin salicylate complexs：
Sequentially add salicylic acid 0.1379g (1mmol), three (adjacent bromobenzyl) chlorinations in order in 100ml round-bottomed flasks
Tin 0.6640g (1mmol), triethylamine 0.1015g (1mmol), etoh solvent 35mL are anti-under conditions of being 50~65 DEG C in temperature
Answer 24h；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains colourless transparent crystal, as three (adjacent bromines
Benzyl) tin salicylate complex.Yield：71%, fusing point：120-122℃.
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
FT-IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-
C),428v(Sn-O)。
Its crystallographic data：Crystal category anorthic system, space groupB=1.12514
(11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=
2, V=1.3637 (2) nm3, Dc=1.865Mgm-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of ＜ θ ＜
27.60 °, crystalline size：0.23x 0.21x 0.20mm, R=0.0369, wR=0.0751.
Embodiment 5：
The preparation of three (adjacent bromobenzyl) tin salicylate complexs：
Sequentially add salicylic acid 0.1387g (1mmol), three (adjacent bromobenzyl) chlorinations in order in 100ml round-bottomed flasks
Tin 0.6975g (1.05mmol), triethylamine 0.1019g (1mmol), etoh solvent 37mL, in the condition that temperature is 50~65 DEG C
Lower reaction 24h；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains colourless transparent crystal, as three
(adjacent bromobenzyl) tin salicylate complex.Yield：71%, fusing point：120-122℃.
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
FT-IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-
C),428v(Sn-O)。
Its crystallographic data：Crystal category anorthic system, space groupB=1.12514
(11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=
2, V=1.3637 (2) nm3, Dc=1.865Mgm-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of ＜ θ ＜
27.60 °, crystalline size：0.23x 0.21x 0.20mm, R=0.0369, wR=0.0751.
Embodiment 6：
The preparation of three (adjacent bromobenzyl) tin salicylate complexs：
Sequentially add salicylic acid 0.2763g (2mmol), three (adjacent bromobenzyl) chlorinations in order in 100ml round-bottomed flasks
Tin 1.3281g (2mmol), triethylamine 0.2026g (2mmol), etoh solvent 70mL are anti-under conditions of being 50~65 DEG C in temperature
Answer 24h；Cooling, filtering, solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, obtains colourless transparent crystal, as three (adjacent bromines
Benzyl) tin salicylate complex.Yield：68%, fusing point：120-122℃.
Elementary analysis (C28H23Br3O3Sn)：Theoretical value：C, 43.91；H, 3.03.Measured value：C, 43.87；H, 3.01.
FT-IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-
C),428v(Sn-O)。
Its crystallographic data：Crystal category anorthic system, space groupB=1.12514
(11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=
2, V=1.3637 (2) nm3, Dc=1.865Mgm-3, μ (MoKa)=5.360mm-1, F (000)=740,2.40 ° of ＜ θ ＜
27.60 °, crystalline size：0.23x 0.21x 0.20mm, R=0.0369, wR=0.0751.
Test example：
Three (adjacent bromobenzyl) tin salicylate complexs of the present invention, its Anticancer Activity in vitro measure is to pass through MTT experiment
What method was realized.
MTT analyses method：
3- (4,5-Dimethylthiazol-2-yl) -2,5-diArenyltetrazolium is reduced with metabolism
Based on bromide.Succinate dehydrogenase in living cells mitochondria can make exogenous MTT be reduced to the bluish violet of water-insoluble
Crystallization first a ceremonial jade-ladle, used in libation (Formazan) is simultaneously deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) (DMSO) can dissolve cell
In first a ceremonial jade-ladle, used in libation, with ELIASA determine characteristic wavelength optical density, living cells quantity can be reflected indirectly.
Three (adjacent bromobenzyl) tin salicylate complexs of the preparation of embodiment 1 are determined to human lung carcinoma cell using mtt assay
(NCI-H460), human lung carcinoma cell (A549), the inhibitory activity of human breast cancer cell (MCF7).
Cell line and cultivating system：NCI-H460, A549 and MCF7 cell line are derived from American. tissue incubator (ATCC).With
RPMI1640 (GIBICO companies) culture medium containing 10% hyclone, in 5% (volume fraction) CO2, 37 DEG C of saturated humidity trainings
Support and in vitro culture is carried out in case.
Test process：Test decoction (0.0032uM-10uM) is added separately to each hole according to the concentration gradient of concentration
In, each concentration sets 3 parallel holes.Experiment is divided into drug test group (the test medicine for being separately added into various concentrations), control group (only
Add nutrient solution and cell, be not added with testing medicine) and blank group (only adding nutrient solution, be not added with cell and test medicine).By the hole after dosing
Plate is placed in 37 DEG C, 5%CO272h is cultivated in incubator.The activity of control drug determines according to the method for test sample.Cultivating
In orifice plate after 72h, add MTT40uL (being made into 4mg/mL with D-Hanks buffer solutions) per hole.After 37 DEG C are placed 4h, remove
Supernatant.Add 150uL DMSO per hole, vibrate 5min, make Formazan crystallization dissolvings.Finally, existed using automatic ELIASA
The optical density in each hole is detected at 570nm wavelength.
Data processing：Data processing uses GraAr Pad Prism version5.0 programs, compound IC50Pass through program
In have S-shaped dose response nonlinear regression model (NLRM) be fitted to obtain.
With MTT analytic approach to human lung carcinoma cell (NCI-H460) cell line, human lung carcinoma cell (A549) cell line, people's mammary gland
Cancer cell (MCF7) cell line is analyzed, and determines its IC50Value, as a result as shown in table 1, conclusion is：From data in table, sheet
Three (adjacent bromobenzyl) tin salicylate complexs of invention are higher to human lung cancer, human breast carcinoma activity as cancer therapy drug, can make
For the candidate compound of cancer therapy drug.
The di-n-butyl tin O-methoxy nicotinate complex cancer therapy drug external activity test data of table 1.
| Human lung carcinoma cell | Human lung carcinoma cell | Human breast cancer cell | |
| Cell line | NCI-H460 | A549 | MCF7 |
| IC50μM | 6.835 | 3.763 | 36 |
Three (adjacent bromobenzyl) tin salicylate complexs prepared by remaining embodiment are with mtt assay to human lung carcinoma cell (NCI-
H460), the same test example of active anticancer method of testing of human lung carcinoma cell (A549) and human breast cancer cell (MCF7), test result
It is essentially identical with table 1.
Claims (8)
- One kind three 1. (adjacent bromobenzyl) tin salicylate complex, it is characterised in that be the complex of following structure formula (I)：
- 2. three (adjacent bromobenzyl) tin salicylate complexs of one kind as claimed in claim 1, it is characterised in that its infrared spectrum Data：FT-IR(KBr,v/cm-1):3051,2974v(C-H),1632vas(COO-),1391vs(COO-),590v(Sn-C), 428v(Sn-O)。
- 3. three (adjacent bromobenzyl) tin salicylate complex as claimed in claim 1, it is characterised in that three described (adjacent bromines Benzyl) tin salicylate complex is crystal structure, its crystallographic data is as follows：Crystal category anorthic system, space groupa =1.12298 (11) nm, b=1.12514 (11) nm, c=1.13003 (11) nm, α=104.1190 (10) °, β=99.3640 (10) °, γ=91.0520 (10) °, Z=2, V=1.3637 (2) nm3, the center tin in molecule forms four with coordination atom and matches somebody with somebody Position distortion tetrahedral configuration.
- 4. the preparation method of three (adjacent bromobenzyl) tin salicylate complexs described in any one of claims 1 to 3 claim, Characterized in that, sequentially add salicylic acid, three (adjacent bromobenzyl) stannic chlorides, triethylamine and solvent second in order in reaction vessel Alcohol, react 8~24h under conditions of being 50~65 DEG C in temperature；Cooling, filtering, solvent is controlled to wave under conditions of 20~35 DEG C Hair crystallization, obtains colourless transparent crystal, as three (adjacent bromobenzyl) tin salicylate complexs.
- 5. preparation method as claimed in claim 4, it is characterised in that the salicylic acid, three (adjacent bromobenzyl) stannic chlorides, three second The amount ratio of the material of amine is 1:1~1.05:1.
- 6. preparation method as claimed in claim 4, it is characterised in that the etoh solvent dosage is every mM three (adjacent bromine Benzyl) stannic chloride adds 20~35 milliliters.
- 7. three (adjacent bromobenzyl) tin salicylate complexs described in any one of claims 1 to 3 claim are preparing treatment Application in cancer drug.
- 8. the application described in claim 7, wherein the cancer is lung cancer, breast cancer.
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| CN108864174A (en) * | 2018-04-02 | 2018-11-23 | 衡阳师范学院 | Three (o-chlorobenzyl) tin salicylates of one kind and preparation method and application |
| CN108997410A (en) * | 2018-04-02 | 2018-12-14 | 衡阳师范学院 | Three (adjacent bromobenzyl) tin -2- ester thiohenic acids of one kind and preparation method and application |
| CN109134528A (en) * | 2018-04-02 | 2019-01-04 | 衡阳师范学院 | Three (adjacent bromobenzyl) tin phenyl acrylates of one kind and preparation method and application |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864174A (en) * | 2018-04-02 | 2018-11-23 | 衡阳师范学院 | Three (o-chlorobenzyl) tin salicylates of one kind and preparation method and application |
| CN108997410A (en) * | 2018-04-02 | 2018-12-14 | 衡阳师范学院 | Three (adjacent bromobenzyl) tin -2- ester thiohenic acids of one kind and preparation method and application |
| CN109134528A (en) * | 2018-04-02 | 2019-01-04 | 衡阳师范学院 | Three (adjacent bromobenzyl) tin phenyl acrylates of one kind and preparation method and application |
| CN108864174B (en) * | 2018-04-02 | 2020-12-11 | 衡阳师范学院 | Tris (o-chlorobenzyl) tin salicylate, preparation method and application thereof |
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