CN103304592B - A kind of dibutyl tin 4-methyl benzoic acid ester of ladder structure and preparation method and application - Google Patents
A kind of dibutyl tin 4-methyl benzoic acid ester of ladder structure and preparation method and application Download PDFInfo
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Abstract
The dibutyl tin 4-methyl benzoic acid ester of a kind of ladder structure disclosed by the invention, the compound for following structural formula (1):
, wherein: R represents normal-butyl.The invention also discloses the preparation method of the dibutyl tin 4-methyl benzoic acid ester of this ladder structure.The dibutyl tin 4-methyl benzoic acid ester of ladder structure of the present invention has good antitumour activity, it can prepare anti-liver cancer, anti-nasopharyngeal carcinoma, anti-breast cancer, anti-lung cancer, drugs against colon cancer for raw material.Compared with the platinum-containing anticancer drug generally used at present, dibutyl tin 4-methyl benzoic acid ester of the present invention has the features such as antitumour activity is high, cost is low, preparation method is simple, for exploitation cancer therapy drug provides new way.
Description
Technical field
The present invention relates to dibutyl tin 4-methyl benzoic acid ester technical field, dibutyl tin 4-methyl benzoic acid ester being specifically related to a kind of ladder structure and preparation method thereof, and prepare the application in antitumor drug.
Background technology
Organotin is the compound that a class has compared with high biological activity, has wide practical use in sterilization, cancer therapy drug preparation.There are some researches show, the radicals R of organotin and playing an important role with the antitumour activity of ligand structure to compound of tin atom coordination, e.g., the antitumour activity of cyclohexyl, normal-butyl and phenyltin compound is comparatively strong, and ethyl takes second place, and methyl is non-activity almost.Chinese patent CN101402650B discloses a kind of dibutyl tin and quinolinecarboxylic acid title complex preparing to treat in cancer of the stomach, nasopharyngeal carcinoma, people's liver cancer or leukemic medicine and applies; Chinese patent CN101434616B discloses a kind of dibutyl tin Schiff base complex and applies in preparation treatment cancer of the stomach, nasopharyngeal carcinoma, people's liver cancer or leukemic medicine.The ester compound formed based on aromatic carboxylic acid and dibutyl tin the experiment proved that the material with antitumour activity, the present invention selects the organotin of dibutyl tin dichloride or Dibutyltin oxide, 4-tolyl acid is part, react under certain condition, synthesis obtains the compound stronger to the inhibit activities of human liver cancer cell (HEPG2), KB cell (KB), human breast cancer cell (MCF-7), human lung carcinoma cell (A549), human colon cancer cell (HT-29), for exploitation cancer therapy drug provides new way.
Summary of the invention
An object of the present invention is the dibutyl tin 4-methyl benzoic acid ester providing a kind of ladder structure.
Two of the object of the invention is the preparation method of the dibutyl tin 4-methyl benzoic acid ester providing above-mentioned ladder structure.
Three of the object of the invention is the application of dibutyl tin 4-methyl benzoic acid ester in medicine providing above-mentioned ladder structure.
In order to realize foregoing invention object, the technical solution adopted in the present invention is:
A dibutyl tin 4-methyl benzoic acid ester for ladder structure, the compound for following structural formula (1):
Wherein: R represents normal-butyl.
The preparation method of the dibutyl tin 4-methyl benzoic acid ester of ladder structure: add 4-tolyl acid, Dibutyltin oxide or dibutyl tin dichloride, a solvent anhydrous methanol in order successively in reaction vessel, reacts 8 ~ 12h under stirring and refluxing; Cooling, filters; At pressure 0.005 ~ 0.01MPa, temperature is under 30 ~ 35 ° of C conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain white solid, with methylene chloride-methanol mixed solvent recrystallization, obtain clear crystal, be the dibutyl tin 4-methyl benzoic acid ester of a kind of ladder structure of the present invention; Wherein 4-tolyl acid, dibutyl tin dichloride or Dibutyltin oxide are reactant, anhydrous methanol is reaction solvent, methylene chloride-methanol mixed solvent is crystallization solvent, and reactant 4-tolyl acid is 1:2 ~ 1:2.2 with the amount of substance ratio of Dibutyltin oxide or dibutyl tin dichloride; The consumption of solvent anhydrous methanol is that every mmole Dibutyltin oxide or dibutyl tin dichloride add 20 ~ 25 ml methanol, and in methylene chloride-methanol mixed solvent, the volume ratio of methylene dichloride and methyl alcohol is 1:10 ~ 1:20.
In a preferred embodiment of the invention, in reaction vessel, add 4-tolyl acid, Dibutyltin oxide or dibutyl tin dichloride, anhydrous solvent anhydrous methanol in order successively, catalyst sodium methoxide is 0.1:1 ~ 4.05:1 with the amount of substance ratio of reactant 4-tolyl acid.
The dibutyl tin 4-methyl benzoic acid ester of applicant to above-mentioned ladder structure has carried out anti tumor activity in vitro and has confirmed research, confirm that the dibutyl tin 4-methyl benzoic acid ester of this ladder structure has anti-tumor biological, that is the purposes of the dibutyl tin 4-methyl benzoic acid ester of above-mentioned ladder structure is preparing the application in antitumor drug, is exactly specifically the application in the anti-liver cancer of preparation or anti-nasopharyngeal carcinoma or anti-breast cancer or anti-lung cancer or drugs against colon cancer.
The dibutyl tin 4-methyl benzoic acid ester of ladder structure of the present invention, its crystal structure characteristic is: crystal belongs to oblique system, spacer P2
1/ n, crystallographic parameter: a=1.35954 (6) nm, b=1.39180 (5) nm, c=1.64411 (6) nm, α=γ=90 °, β=106.775 (2) °, Z=2, V=2.9786 (2) nm
3.The Sn formed with tin and Sauerstoffatom is there is in molecule
2o
2planar four-element ring, three tetra-atomic rings utilize Sn-O key atom to condense formation four core tin oxygen bunch ladder structure for bridgehead atom, middle Ring current distribution is the symmetry centre of molecule, has three tin atoms of two Sauerstoffatoms difference bridging ladders in ladder, separately has two methoxyl group Sauerstoffatoms bridging ladder tin atoms respectively.Two 4-tolyl acids utilize its carboxyl oxygen atom to become key to form assorted spirane structure with ladder end tin atom respectively.
The dibutyl tin 4-methyl benzoic acid ester of ladder structure of the present invention has good antitumour activity, it can prepare anti-liver cancer, anti-nasopharyngeal carcinoma, anti-breast cancer, anti-lung cancer, drugs against colon cancer for raw material.Compared with the platinum-containing anticancer drug generally used at present, dibutyl tin 4-methyl benzoic acid ester of the present invention has the features such as antitumour activity is high, cost is low, preparation method is simple, for exploitation cancer therapy drug provides new way.
Accompanying drawing explanation
Fig. 1 is a kind of dibutyl tin 4-methyl benzoic acid ester crystalline structure figure of ladder structure.
Embodiment
Further describe the present invention by following examples, but scope of the present invention should be noted not by any restriction of these embodiments.
Embodiment 1:
Prepare the dibutyl tin 4-methyl benzoic acid ester of ladder structure: in round-bottomed flask, add 4-tolyl acid 0.068g (0.5mmol), dibutyl tin dichloride 0.335g (1.1mmol), sodium methylate 0.109g (2.02mmol) and 25mL anhydrous methanol, stirring heating backflow 12h; Cooling, filters; At pressure 0.005MPa, temperature is under 30 ° of C conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain white solid, with methylene chloride-methanol mixed solvent recrystallization, obtain clear crystal, be the dibutyl tin 4-methyl benzoic acid ester of ladder structure, productive rate: 71%, fusing point: 145 ~ 147 DEG C.
Ultimate analysis (C
50h
92o
8sn
4): theoretical value: C, 46.33; H, 7.15.Measured value: C, 46.61; H, 7.30.
IR(KBr,cm
-1):2957,2925，2859ν(C-H),1623ν
as(COO
-),1405ν
s(COO
-),619ν(Sn-O-Sn),551ν(Sn-C),420ν(Sn-O)。
1HNMR(CDCl
3)δ(ppm):0.90(t,24H,J=6.4,-CH
3,butyl);1.38-1.69(m,48H,SnCH
2CH
2CH
2,butyl);2.40(s,6H,Ar-CH
3);3.49(s,6H,-OCH
3);7.19(s,4H,Ar-H);7.88(s,4H,Ar-H)。
13CNMR(CDCl
3)δ(ppm):13.63-27.87(n-Bu-C);21.47(Ar-CH
3);50.86,51.06(-OCH
3);128.62,129.75,131.70,141.53(Ar-C);172.74(-COO)。
Crystallographic data: oblique system, spacer P2
1/ n, crystallographic parameter: a=1.35954 (6) nm, b=1.39180 (5) nm, c=1.64411 (6) nm, α=γ=90 °, β=106.775 (2) °, Z=2, V=2.9786 (2) nm
3, D
c=1.445Mgm
-3, μ (MoK
α)=1.701mm
-1, F (000)=1312,1.72 ° of < θ < 27.00 °, crystalline size: 0.20 × 0.19 × 0.17mm, R=0.0650, wR=0.1416.
Embodiment 2:
Prepare the dibutyl tin 4-methyl benzoic acid ester of ladder structure: in round-bottomed flask, add 4-tolyl acid 0.068g (0.5mmol), Dibutyltin oxide 0.249g (1.0mmol), sodium methylate 0.003g (0.05mmol) and 20mL anhydrous methanol, stirring heating backflow 12h; Cooling, filters; At pressure 0.01MPa, temperature is under 35 ° of C conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain white solid, with methylene chloride-methanol mixed solvent recrystallization, obtain clear crystal, be the dibutyl tin 4-methyl benzoic acid ester of a kind of ladder structure of the present invention, productive rate: 73%, fusing point: 145 ~ 147 DEG C.
Ultimate analysis (C
50h
92o
8sn
4): theoretical value: C, 46.33; H, 7.15. measured value: C, 46.61; H, 7.30.
IR(KBr,cm
-1):2957,2925,2859ν(C-H),1623ν
as(COO
-),1405ν
s(COO
-),619ν(Sn-O-Sn),551ν(Sn-C),420ν(Sn-O)。
1HNMR(CDCl
3)δ(ppm):0.90(t，24H,J=6.4,-CH
3,butyl);1.38-1.69(m,48H,SnCH
2CH
2CH
2,butyl);2.40(s,6H,Ar-CH
3);3.49(s,6H,-OCH
3);7.19(s,4H,Ar-H);7.88(s,4H,Ar-H)。
13CNMR(CDCl
3)δ(ppm):13.63-27.87(n-Bu-C);21.47(Ar-CH
3);50.86,51.06(-OCH
3);128.62,129.75,131.70,141.53(Ar-C);172.74(-COO)。
Crystallographic data: oblique system, spacer P2
1/ n, crystallographic parameter: a=1.35954 (6) nm, b=1.39180 (5) nm, c=1.64411 (6) nm, α=γ=90 °, β=106.775 (2) °, Z=2, V=2.9786 (2) nm
3, D
c=1.445Mgm
-3, μ (MoK
α)=1.701mm
-1, F (000)=1312,1.72 ° of < θ < 27.00 °, crystalline size: 0.20 × 0.19 × 0.17mm, R=0.0650, wR=0.1416.
Embodiment 3:
Prepare the dibutyl tin 4-methyl benzoic acid ester of ladder structure: in round-bottomed flask, add 4-tolyl acid 0.135g (1.0mmol), dibutyl tin dichloride 0.638g (2.1mmol), sodium methylate 0.219g (4.05mmol) and 45mL anhydrous methanol, stir lower reflux 8h; Cooling, filters; At pressure 0.005MPa, temperature is under 33 ° of C conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain white solid, with methylene chloride-methanol mixed solvent recrystallization, obtain clear crystal, be the dibutyl tin 4-methyl benzoic acid ester of a kind of ladder structure of the present invention, productive rate: 69%, fusing point: 145 ~ 147 DEG C.
Ultimate analysis (C
50h
92o
8sn
4): theoretical value: C, 46.33; H, 7.15. measured value: C, 46.61; H, 7.30.
IR(KBr,cm
-1):2957,2925,2859ν(C-H),1623ν
as(COO
-),1405ν
s(COO
-),619ν(Sn-O-Sn),551ν(Sn-C),420ν(Sn-O)。
1HNMR(CDCl
3)δ(ppm):0.90(t,24H,J=6.4,-CH
3,butyl);1.38-1.69(m,48H,SnCH
2CH
2CH
2,butyl);2.40(s,6H,Ar-CH
3);3.49(s,6H,-OCH
3);7.19(s,4H,Ar-H);7.88(s,4H,Ar-H)。
13CNMR(CDCl
3)δ(ppm):13.63-27.87(n-Bu-C);21.47(Ar-CH
3);50.86,51.06(-OCH
3);128.62,129.75,131.70,141.53(Ar-C);172.74(-COO)。
Crystallographic data: oblique system, spacer P2
1/ n, crystallographic parameter: a=1.35954 (6) nm, b=1.39180 (5) nm, c=1.64411 (6) nm, α=γ=90 °, β=106.775 (2) °, Z=2, V=2.9786 (2) nm
3, D
c=1.445Mgm
-3, μ (MoK
α)=1.701mm
-1, F (000)=1312,1.72 ° of < θ < 27.00 °, crystalline size: 0.20 × 0.19 × 0.17mm, R=0.0650, wR=0.1416.
Embodiment 4:
Prepare the dibutyl tin 4-methyl benzoic acid ester of ladder structure: in round-bottomed flask, add 4-tolyl acid 0.135g (1.0mmol), Dibutyltin oxide 0.498g (2.0mmol), sodium methylate 0.005g (0.1mmol) and 40mL anhydrous methanol, stir lower reflux 10h; Cooling, filters; At pressure 0.007MPa, temperature is under 33 ° of C conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain white solid, with methylene chloride-methanol mixed solvent recrystallization, obtain clear crystal, be the dibutyl tin 4-methyl benzoic acid ester of a kind of ladder structure of the present invention, productive rate: 71%, fusing point: 145 ~ 147 DEG C.
Ultimate analysis (C
50h
92o
8sn
4): theoretical value: C, 46.33; H, 7.15. measured value: C, 46.61; H, 7.30.
IR(KBr,cm
-1):2957,2925,2859ν(C-H),1623ν
as(COO
-),1405ν
s(COO
-),619ν(Sn-O-Sn),551ν(Sn-C),420ν(Sn-O)。
1HNMR(CDCl
3)δ(ppm):0.90(t,24H,J=6.4,-CH
3,butyl);1.38-1.69(m,48H,SnCH
2CH
2CH
2,butyl);2.40(s,6H,Ar-CH
3);3.49(s,6H,-OCH
3);7.19(s,4H,Ar-H);7.88(s,4H,Ar-H)。
13CNMR(CDCl
3)δ(ppm):13.63-27.87(n-Bu-C);21.47(Ar-CH
3);50.86,51.06(-OCH
3);128.62,129.75,131.70,141.53(Ar-C);172.74(-COO)。
Crystallographic data: oblique system, spacer P2
1/ n, crystallographic parameter: a=1.35954 (6) nm, b=1.39180 (5) nm, c=1.64411 (6) nm, α=γ=90 °, β=106.775 (2) °, Z=2, V=2.9786 (2) nm
3, D
c=1.445Mgm
-3, μ (MoK
α)=1.701mm
-1, F (000)=1312,1.72 ° of < θ < 27.00 °, crystalline size: 0.20 × 0.19 × 0.17mm, R=0.0650, wR=0.1416.
Test example:
The dibutyl tin 4-methyl benzoic acid ester of ladder structure of the present invention, its Anticancer Activity in vitro is measured and is realized by MTT experiment method.
MTT analytical method:
Based on metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide.Succinodehydrogenase in viable cell plastosome can make exogenous MTT be reduced to water-insoluble bluish voilet crystallization first a ceremonial jade-ladle, used in libation (Formazan) and be deposited in cell, and dead cell is without this function.First a ceremonial jade-ladle, used in libation in dimethyl sulfoxide (DMSO) (DMSO) energy dissolved cell, measures the optical density(OD) of characteristic wavelength, can indirectly reflect viable cell quantity by microplate reader.
Mtt assay is adopted to measure the dibutyl tin 4-methyl benzoic acid ester (test medicine) of embodiment 1 to 4 ladder structure to the inhibit activities of human liver cancer cell (HEPG2), KB cell (KB), human breast cancer cell (MCF-7), human lung carcinoma cell (A549), human colon cancer cell (HT-29).
Cell strain and culture system: HT-29, HEPG2, MCF-7, KB and A549 cell strain takes from American. tissue incubator (ATCC).With RPMI1640 (GIBICO company) substratum containing 10% foetal calf serum, at 5% (volume fraction) CO
2, carry out vitro culture in 37 DEG C of saturated humidity incubators.
Test process: join in each hole respectively by testing the concentration gradient of liquid (0.1nM-10uM) according to concentration, each concentration establishes 6 parallel holes.Experiment is divided into drug test group (adding the test medicine of different concns respectively), control group (only add nutrient solution and cell, do not add test medicine) and blank group (only add nutrient solution, do not add cell and test medicine).Orifice plate after dosing is placed in 37 DEG C, 5%CO
272h is cultivated in incubator.The activity of control drug measures according to the method for test sample.In orifice plate after having cultivated 72h, every hole adds MTT40uL (being made into 4mg/mL with D-Hanks damping fluid).After placing 4h at 37 DEG C, remove supernatant liquor.Every hole adds 150uLDMSO, and vibration 5min, makes Formazan dissolving crystallized.Finally, automatic microplate reader is utilized to detect the optical density(OD) in each hole at 570nm wavelength place.
Data processing: data processing uses GraphPadPrismversion5.0 program, Compound I C
50carry out matching by the nonlinear regression model (NLRM) in program with S shape dose response to obtain.
With MTT analytical method, human liver cancer cell (HEPG2) cell strain, KB cell (KB) cell strain, human breast cancer cell (MCF-7) cell strain, human lung carcinoma cell (A549) cell strain, human colon cancer cell (HT-29) cell strain are analyzed, measure its IC
50value, result is as shown in table 1, conclusion is: from data in table, cancer therapy drug is used as with the dibutyl tin 4-methyl benzoic acid ester of ladder structure of the present invention, higher to people's liver cancer, human nasopharyngeal carcinoma, human breast carcinoma, people's lung cancer, human colon carcinoma antitumour activity, can be used as the candidate compound of cancer therapy drug.
The dibutyl tin 4-methyl benzoic acid ester cancer therapy drug external activity test data of table 1 ladder structure
Claims (5)
1. a dibutyl tin 4-methyl benzoic acid ester for ladder structure, is characterized in that, the compound for following structural formula (1):
Wherein: R represents normal-butyl;
The compound of described structural formula (1) is crystalline structure, and its crystal structure characteristic is: crystal belongs to oblique system, spacer P2
1/ n, crystallographic parameter: a=1.35954 (6) nm, b=1.39180 (5) nm, c=1.64411 (6) nm, α=γ=90 °, β=106.775 (2) °, Z=2, V=2.9786 (2) nm
3; The Sn formed with tin and Sauerstoffatom is there is in molecule
2o
2planar four-element ring, three tetra-atomic rings utilize Sn-O key atom to condense formation four core tin oxygen bunch ladder structure for bridgehead atom, middle Ring current distribution is the symmetry centre of molecule, has three tin atoms of two Sauerstoffatoms difference bridging ladders in ladder, separately has two methoxyl group Sauerstoffatoms bridging ladder tin atoms respectively; Two 4-tolyl acids utilize its carboxyl oxygen atom to become key to form assorted spirane structure with ladder end tin atom respectively.
2. the preparation method of the dibutyl tin 4-methyl benzoic acid ester of a ladder structure according to claim 1, it is characterized in that, in reaction vessel, add 4-tolyl acid, Dibutyltin oxide or dibutyl tin dichloride, sodium methylate, solvent anhydrous methanol in order successively, under stirring and refluxing, react 8 ~ 12h; Cooling, filters; At pressure 0.005 ~ 0.01MPa, temperature is under 30 ~ 35 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtains white solid, with methylene chloride-methanol mixed solvent recrystallization, obtains clear crystal, is the dibutyl tin 4-methyl benzoic acid ester of described ladder structure; Wherein 4-tolyl acid, dibutyl tin dichloride or Dibutyltin oxide are reactant, anhydrous methanol is reaction solvent, methylene chloride-methanol mixed solvent is crystallization solvent, and reactant 4-tolyl acid is 1:2 ~ 1:2.2 with the amount of substance ratio of Dibutyltin oxide or dibutyl tin dichloride; The consumption of solvent anhydrous methanol is that every mmole Dibutyltin oxide or dibutyl tin dichloride add 20 ~ 25 ml methanol, and in methylene chloride-methanol mixed solvent, the volume ratio of methylene dichloride and methyl alcohol is 1:10 ~ 1:20.
3. preparation method as claimed in claim 2, it is characterized in that, in reaction vessel, add 4-tolyl acid, Dibutyltin oxide or dibutyl tin dichloride, anhydrous solvent anhydrous methanol in order successively, catalyst sodium methoxide is 0.1:1 ~ 4.05:1 with the amount of substance ratio of reactant 4-tolyl acid.
4. the dibutyl tin 4-methyl benzoic acid ester of a kind of ladder structure according to claim 1 is preparing the application in antitumor drug.
5. application according to claim 4, is characterized in that: tumour behaviour liver cancer, nasopharyngeal carcinoma, mammary cancer, lung cancer or colorectal carcinoma described in this.
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