CN103450253B - A kind of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure and preparation method and application - Google Patents

A kind of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure and preparation method and application Download PDF

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CN103450253B
CN103450253B CN201310407007.0A CN201310407007A CN103450253B CN 103450253 B CN103450253 B CN 103450253B CN 201310407007 A CN201310407007 A CN 201310407007A CN 103450253 B CN103450253 B CN 103450253B
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dibutyl tin
acid esters
ladder structure
nitrobenzoyl acid
ladder
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CN103450253A (en
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庾江喜
邝代治
冯泳兰
张复兴
蒋伍玖
许志锋
朱小明
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Hengyang Normal University
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Abstract

The dibutyl tin 4-nitrobenzoyl acid esters of a kind of ladder structure disclosed by the invention, it is characterized in that, be the title complex of following structural formula (1), wherein Bu represents normal-butyl.The invention also discloses the preparation method of the title complex of structural formula (1) and preparing the application in antitumor drug.

Description

A kind of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure and preparation method and application
Technical field
The present invention relates to a kind of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure, and preparation method thereof, and this title complex is preparing the application in antitumor drug.
Background technology
Organotin is the organometallics that a class contains Sn-C key, has higher biological activity, the field such as to prepare have a wide range of applications at sterilization, desinsection, cancer therapy drug.Existing research shows, the alkyl R in organotin is the principal element determining compound anti-cancering activity height, and e.g., the antitumour activity of cyclohexyl, normal-butyl and phenyltin compound is comparatively strong, and ethyl takes second place, and methyl is then almost without antitumour activity.The structure of part also plays an important role to the antitumour activity of title complex and the broad spectrum of killing cancer cells, and experiment proves, the biological activity of organotin carboxylate title complex is often high than corresponding organo-tin compound, as:
Disclosed two [three (2-methyl-2-phenyl propyl) tin] monocarboxylate of European patent EP 0177785B1 has stronger biological activity than two [three (2-methyl-2-phenyl propyl) tin] oxide compound; Document (SCI; 2008; 29 (9): 1781-1785.) report; the inhibit activities of dibutyl tin carboxylicesters to Gram-negative and positive bacteria is obviously better than Dibutyltin oxide, and under low concentration, have the function of tumor inhibition stronger than Dibutyltin oxide.
The experiment proved that the material with antitumour activity based on organic tin compound, the present invention selects 4-nitrobenzoic acid to be organic acid part, react under certain condition with Dibutyltin oxide, dibutyl tin dichloride respectively, synthesis obtains has compound compared with strong inhibitory activity, for exploitation cancer therapy drug provides new way to human cervical carcinoma cell (Hela), human breast cancer cell (MCF7), human liver cancer cell (HepG2), human colon cancer cell (Colo205), human lung carcinoma cell (NCI-H460).
Summary of the invention
An object of the present invention is the dibutyl tin 4-nitrobenzoyl acid esters providing a kind of ladder structure.
Two of the object of the invention is the preparation method of the dibutyl tin 4-nitrobenzoyl acid esters providing above-mentioned a kind of ladder structure.
Three of the object of the invention is the application of dibutyl tin 4-nitrobenzoyl acid esters in medicine providing above-mentioned a kind of ladder structure.
In order to realize foregoing invention object, the technical solution adopted in the present invention is:
A dibutyl tin 4-nitrobenzoyl acid esters for ladder structure, the title complex for following structural formula (1):
Wherein Bu represents normal-butyl.
The title complex of described structural formula (1) is crystalline structure, its crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3; By Sn in molecule 2o 2tetra-atomic ring is fused into four core tin oxygen ladder structures, and 2 4-nitrobenzoic acids utilize its carboxyl oxygen atom to hold tin atom to become key to form assorted spirane structure with ladder respectively.
The preparation method of the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure: add 4-nitrobenzoic acid 1mmol, Dibutyltin oxide 1 ~ 1.2mmol or dibutyl tin dichloride 1 ~ 1.2mmol, sodium methylate 0 ~ 1.2mmol, solvent anhydrous methanol 15 ~ 50mL in reaction vessel in order successively, reacts 8 ~ 12h under stirring and refluxing; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.
The dibutyl tin 4-nitrobenzoyl acid esters of applicant to above-mentioned a kind of ladder structure has carried out anti tumor activity in vitro and has confirmed research, confirm that the dibutyl tin 4-nitrobenzoyl acid esters of this kind of ladder structure has anti-tumor biological, that is the purposes of the dibutyl tin 4-nitrobenzoyl acid esters of above-mentioned a kind of ladder structure is preparing the application in antitumor drug, is exactly specifically preparing the application in anti-cervical cancer or anti-breast cancer or anti-liver cancer or inhibitor against colon carcinoma cells or anti-lung-cancer medicament.
The dibutyl tin 4-nitrobenzoyl acid esters of a kind of ladder structure of the present invention has good antitumour activity, it can prepare anti-cervical cancer, anti-breast cancer, anti-liver cancer, inhibitor against colon carcinoma cells, anti-lung-cancer medicament for raw material.Compared with the platinum-containing anticancer drug generally used at present, the dibutyl tin 4-nitrobenzoyl acid esters of a kind of ladder structure 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-nitrobenzoic acid crystalline esters molecular structure of ladder structure.
Specific implementation method
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:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), Dibutyltin oxide 0.249g (1mmol), 15mL anhydrous methanol in order successively, under stirring and refluxing, react 8h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 71.0%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。
1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 2:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), Dibutyltin oxide 0.274g (1.1mmol), 25mL anhydrous methanol in order successively, under stirring and refluxing, react 10h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 74.7%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。
1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 3:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), Dibutyltin oxide 0.261g (1.05mmol), 35mL anhydrous methanol in order successively, under stirring and refluxing, react 9h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 73.5%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。
1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 4:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), Dibutyltin oxide 0.299g (1.2mmol), 50mL anhydrous methanol in order successively, under stirring and refluxing, react 12h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 78.6%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。 1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 5:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), dibutyl tin dichloride 0.304g (1mmol), sodium methylate 0.054g (1mmol), 15mL anhydrous methanol in order successively, under stirring and refluxing, react 8h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 72.4%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。 1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 6:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), dibutyl tin dichloride 0.319g (1.05mmol), sodium methylate 0.057g (1.05mmol), 25mL anhydrous methanol in order successively, under stirring and refluxing, react 10h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 73.8%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。
1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 7:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), dibutyl tin dichloride 0.334g (1.1mmol), sodium methylate 0.059g (1.1mmol), 35mL anhydrous methanol in order successively, under stirring and refluxing, react 11h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 76.9%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。
1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Embodiment 8:
A kind of preparation of dibutyl tin 4-nitrobenzoyl acid esters of ladder structure:
In round-bottomed flask, add 4-nitrobenzoic acid 0.167g (1mmol), dibutyl tin dichloride 0.365g (1.2mmol), sodium methylate 0.065g (1.2mmol), 50mL anhydrous methanol in order successively, under stirring and refluxing, react 12h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.Productive rate 80.3%.Fusing point: 93 ~ 95 DEG C.
Ultimate analysis (C 48h 80n 2o 12sn 4): theoretical value: C42.64, H5.96, N2.07; Measured value: C42.63, H5.97, N2.05.
IR(KBr,cm -1)：3078(w，ν Ar-H)，2957，2926，2860(m，ν C-H)，1576(vs，ν asCOO)，1452(w，ν C=C)，1339(s，ν sCOO)，474(m，ν Sn-C)，420(w，ν Sn-O)。 1HNMR(CDCl 3,500MHz),δ(ppm):8.12～8.25(m，8H，Ar-H)，4.01(s，6H，CH 3O)，0.89～1.73(m，72H，SnCH 2CH 2CH 2CH 3)。
13CNMR(CDCl 3,125MHz),δ(ppm):13.65(-CH 3),25.67(SnCH 2CH 2CH 2CH 3),26.84(SnCH 2CH 2CH 2CH 3),27.47(SnCH 2CH 2CH 2CH 3),123.18,130.49,140.92,149.77(Ar-C),163.73(-COO)。
Crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3, D c=1.440Mgm -3, μ (MoK α)=1.633mm -1, F (000)=2712, R=0.0559, wR=0.1417.
Test example:
The dibutyl tin 4-nitrobenzoyl acid esters of a kind 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 player (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-nitrobenzoyl acid esters of this kind of ladder structure to the inhibit activities of human cervical carcinoma cell (Hela), human breast cancer cell (MCF7), human liver cancer cell (HepG2), human colon cancer cell (Colo205), human lung carcinoma cell (NCI-H460).
Cell strain and culture system: Hela, MCF7, HepG2, Colo205 and NCI-H460 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, title complex IC 50carry out matching by the nonlinear regression model (NLRM) in program with S shape dose response to obtain.
With MTT analytical method, human cervical carcinoma cell (Hela) cell strain, human breast cancer cell (MCF7) cell strain, human liver cancer cell (HepG2) cell strain, human colon cancer cell (Colo205) cell strain, human lung carcinoma cell (NCI-H460) 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-nitrobenzoyl acid esters of a kind of ladder structure of the present invention, higher to human cervical carcinoma, human breast carcinoma, people's liver cancer, human colon carcinoma, people's lung cancer activity, can be used as the candidate compound of cancer therapy drug.
The dibutyl tin 4-nitrobenzoyl acid esters cancer therapy drug external activity test data of table 1 ladder structure

Claims (4)

1. a dibutyl tin 4-nitrobenzoyl acid esters for ladder structure, is characterized in that, the title complex for following structural formula (1):
Wherein Bu represents normal-butyl;
The title complex of described structural formula (1) is crystalline structure, its crystallographic data: rhombic system, spacer P2 12 12 1, a=1.57159 (16) nm, b=1.70176 (19) nm, c=2.3323 (3) nm, α=β=γ=90 °, Z=4, V=6.2376 (12) nm 3; By Sn in molecule 2o 2tetra-atomic ring is fused into four core tin oxygen ladder structures, and 2 4-nitrobenzoic acids utilize its carboxyl oxygen atom to hold tin atom to become key to form assorted spirane structure with ladder respectively.
2. the preparation method of the dibutyl tin 4-nitrobenzoyl acid esters of a kind of ladder structure according to claim 1, it is characterized in that in reaction vessel, add 4-nitrobenzoic acid 1mmol, Dibutyltin oxide 1 ~ 1.2mmol or dibutyl tin dichloride 1 ~ 1.2mmol, sodium methylate 0 ~ 1.2mmol, solvent anhydrous methanol 15 ~ 50mL in order successively, under stirring and refluxing, react 8 ~ 12h; Cooling, filters; Under 25 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain colourless transparent crystal, be the dibutyl tin 4-nitrobenzoyl acid esters of ladder structure.
3. the dibutyl tin 4-nitrobenzoyl acid esters of a kind of ladder structure according to claim 1 is preparing the application in antitumor drug.
4. application according to claim 3, wherein said tumour is human cervical carcinoma, mammary cancer, liver cancer, colorectal carcinoma, lung cancer.
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DD275690A1 (en) * 1988-09-19 1990-01-31 Greiz Doelau Chemie PROCESS FOR THE PRODUCTION OF ORGANOZIN NITROGENS
CN103087115A (en) * 2013-02-04 2013-05-08 衡阳师范学院 Ferrocenyl-containing tributyltin benzoate coordination polymer, and preparation method and application thereof
CN103275115A (en) * 2013-06-17 2013-09-04 衡阳师范学院 Dibutyltin pepper acid ester with trapezoidal structure, and preparation method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD275690A1 (en) * 1988-09-19 1990-01-31 Greiz Doelau Chemie PROCESS FOR THE PRODUCTION OF ORGANOZIN NITROGENS
CN103087115A (en) * 2013-02-04 2013-05-08 衡阳师范学院 Ferrocenyl-containing tributyltin benzoate coordination polymer, and preparation method and application thereof
CN103275115A (en) * 2013-06-17 2013-09-04 衡阳师范学院 Dibutyltin pepper acid ester with trapezoidal structure, and preparation method and application thereof

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