CN109369702A - A kind of one-dimensional chain stannous phenide complex of thienyl-containing ligand - Google Patents
A kind of one-dimensional chain stannous phenide complex of thienyl-containing ligand Download PDFInfo
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- CN109369702A CN109369702A CN201811576525.4A CN201811576525A CN109369702A CN 109369702 A CN109369702 A CN 109369702A CN 201811576525 A CN201811576525 A CN 201811576525A CN 109369702 A CN109369702 A CN 109369702A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/22—Tin compounds
- C07F7/2284—Compounds with one or more Sn-N linkages
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
The invention discloses a kind of one-dimensional chain stannous phenide complexs of thienyl-containing ligand, are the complex of following structure formula (I), wherein R is phenyl.The invention also discloses the preparation method of the one-dimensional chain stannous phenide complex of the thienyl-containing ligand and preparing the application in anticancer drug.
Description
Technical field
The present invention relates to one-dimensional chain stannous phenide complexs of a kind of thienyl-containing ligand and preparation method thereof, and should
The one-dimensional chain stannous phenide complex of thienyl-containing ligand is preparing the application in anticancer drug.
Background technique
Acylhydrazone is condensed by aldehydes or ketones and hydrazides, has good bioactivity, stronger configurational energy
Power and multiplicity coordination mode, and medicine, pesticide, material and in terms of have a wide range of applications.In recent years,
Domestic and international many researchers compare it in terms of bioactivity in depth to be studied, and discovery acylhydrazone has
The various actives such as anticancer, sterilization, anti-inflammatory.Organotin is the metallo-organic compound containing Sn-C key, and it is extensive studies have shown that
Many organotin complexes have excellent anti-tumor activity.By acylhydrazone ligand in conjunction with organotin, it is expected to obtain selectivity more
By force, the better anti-tumor drug of effect.
Patent CN 102718794A discloses a kind of double acylhydrazone class Schiff stannous phenide complexs and its anti-in preparation
Adenocarcinoma of lung, colon cancer, leukaemia cell drug in application.
Patent CN 101851251A discloses a kind of dibutyl tin complex of acylhydrazone class Schiff ligand and its is making
Standby treatment liver cancer, adenocarcinoma of lung, breast cancer, prostate cancer, colon cancer or the early application in the drug of young grain leukaemia.
Series of patents CN105777799A, CN106220675A, CN106279250A, CN106279260A,
CN106317105A、CN106366118A、CN106380480A、CN105693763A、CN106220668A、
CN106220670A、CN106220676A、CN106220678A、CN106279252A、CN106279258A、
CN106279261A、CN106336429A、CN105732697A、CN106220669A、CN106220672A、
CN106220674A、CN106220677A、CN106366119A、CN105384770A、CN105541898A、
CN105601663A、CN105601664A、CN105237563A、CN105237564A、CN105399765A、CN105399764A
It discloses the organotin complex of serial substituted benzoyl benzoyl hydrazone and preparation method and is preparing the application in anticancer drug,
Described in the cancer cell applied be human colon cancer cell (Colo205) or human liver cancer cell (HepG2) or breast cancer cell
(MCF7) or cervical cancer cell (Hela) or human lung carcinoma cell (NCI-H460).
Document (Solid State Sciences, 2011,13 (03): 501-507) reports serial substituted benzene toluene
The organotin complex of formyl hydrazone or thenoyl hydrazone.
Document (Inorganica Chimica Acta, 2007,360 (07): 2215-2223) reports serial thiophene
The organotin complex of formyl hydrazone.
Method used by the synthesis of above-mentioned acylhydrazone organotin complex has multistep processes synthesis and one pot process, wherein more
Footwork synthesis step is long, and the reaction time is long, at high cost, low efficiency；Though one pot process reduces synthesis step, there are still
The problem of reaction time is long, and energy consumption is high, low efficiency.To solve the defects of above-mentioned document synthesis, the present invention devises microwave one
The synthetic method of pot method, overcomes the defect of multistep processes and common one kettle way, and synthesis has been obtained to people's colon under certain condition
Cancer cell (Colo205), human liver cancer cell (HepG2), breast cancer cell (MCF7), cervical cancer cell (Hela) and human lung cancer
Cell (NCI-H460) has the acylhydrazone organotin complex of certain inhibitory activity, provides new way for exploitation anticancer drug
Diameter.
Summary of the invention
There is provided a kind of one-dimensional chain stannous phenide complexs of thienyl-containing ligand for the first object of the present invention.
The second object of the present invention is to provide the one-dimensional chain stannous phenide complex preparation side of above-mentioned thienyl-containing ligand
Method.
It is prepared by the one-dimensional chain stannous phenide complex that the third object of the present invention is to provide above-mentioned thienyl-containing ligand
Application in anticancer drug.
A kind of one-dimensional chain stannous phenide complex of thienyl-containing ligand as the first aspect of the present invention is structure
The complex of formula (I)
(I)
Wherein R is phenyl.
The one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention is through elemental analysis, infrared spectroscopy, nuclear-magnetism
Resonance spectrum and X-ray single crystal diffraction structural analysis, as a result as follows:
Elemental analysis (C21H18N2O3SSn): calculated value: C 50.73, H 3.65, N 5.63；Measured value: C 50.79, H 3.76,
N 5.59。
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577,
1529, 1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854,
839, 802, 732, 694, 603, 563, 536, 453, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82
(m, 4H), 7.63 (d, J = 5.2 Hz, 1H), 7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07
(q, J = 7.6 Hz, 2H), 1.28 (t, J = 7.6 Hz, 3H)。
13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.85。
The one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention is crystal structure, and crystal is monoclinic crystal
System, space group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10) nm, c=2.0490 (2) nm, α=γ
=90 °, β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, the Mgm of Dc=1.575-3, m (MoK α)=1.342
mm-1, F (000)=992.
The one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention is structurally characterized in that: tin atom in molecule
For hexa-coordinate distorted octahedron configuration, and the molecule constitutes one dimensional infinite chain structure by Sn-O key.
The one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention, which is characterized in that there is certain heat
Stability range can be stabilized at 252 DEG C or less.
A kind of preparation of the one-dimensional chain stannous phenide complex of thienyl-containing ligand as a second aspect of the invention
Method, it is characterized in that diphenyl stannous chloride, 2- thenoyl are added in microwave reaction tank using microwave one pot process
Hydrazine, 2- batanone acid and solvent anhydrous methanol, react 10 ~ 100 min under conditions of temperature is 60 ~ 120 DEG C, and program is cooled to 25
DEG C, obtain yellow transparent crystal, as the one-dimensional chain stannous phenide complex of thienyl-containing ligand.
In a preferred embodiment of the invention, the diphenyl stannous chloride, 2- thenoyl hydrazine, 2- batanone acid three
The mass ratio of the material of person is 1:(1 ~ 1.05): (1 ~ 1.1).
In a preferred embodiment of the invention, the solvent anhydrous methanol dosage is every mM of diphenyl dichloride
Tin adds 5 ~ 35 milliliters.
In a preferred embodiment of the invention, described program cooling conditions are 0.1 ~ 20 DEG C/h.
It is prepared by a kind of one-dimensional chain stannous phenide complex of thienyl-containing ligand as the third aspect of the present invention
Application in anticancer drug.
Applicant has carried out anti tumor activity in vitro to the one-dimensional chain stannous phenide complex of above-mentioned thienyl-containing ligand
Determining research, it is thus identified that the one-dimensional chain stannous phenide complex of thienyl-containing ligand has certain anticancer bioactive,
That is the purposes of above-mentioned complex is to prepare the application in anticancer drug, be specifically exactly prepare anti-human colon cancer,
Application in human liver cancer, human breast carcinoma, human cervical carcinoma and human lung cancer drug.
The one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention is thin to human colon cancer cell, human liver cancer
Born of the same parents, human breast cancer cell, human cervical carcinoma cell, human lung carcinoma cell etc. show good anticancer activity, and of the invention contains thiophene
The features such as one-dimensional chain stannous phenide complex anticancer activity of pheno ylidene ligands is high, at low cost, preparation method is simple, it is new to develop
Anticancer drug provide new way.
Detailed description of the invention
Fig. 1 is the crystal structure figure of the one-dimensional chain stannous phenide complex of thienyl-containing ligand.
Fig. 2 is the IR spectrogram of the one-dimensional chain stannous phenide complex of thienyl-containing ligand.
Fig. 3 is the one-dimensional chain stannous phenide complex of thienyl-containing ligand1H NMR spectra.
Fig. 4 is the one-dimensional chain stannous phenide complex of thienyl-containing ligand13C NMR spectra.
Fig. 5 is the one-dimensional chain stannous phenide complex of thienyl-containing ligand119Sn NMR spectra.
Fig. 6 is the TG-DTG curve of the one-dimensional chain stannous phenide complex of thienyl-containing ligand.
Specific embodiment
By following embodiment, present invention be described in more detail, 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 the one-dimensional chain stannous phenide complex of thienyl-containing ligand:
0.343g (1.0mmol) diphenyl stannous chloride, 0.142g (1.0mmol) 2- thiophene first are added in microwave reaction tank
Hydrazides, 0.102g (1.0mmol) 2- batanone acid and 20mL solvent anhydrous methanol react 100 under conditions of temperature is 100 DEG C
Min is arranged the program cooling conditions of 20 DEG C/h, is down to 25 DEG C, obtains yellow transparent crystal, the as one-dimensional chain of thienyl-containing ligand
Shape stannous phenide complex.Yield: 85.4%.Fusing point: 252 ~ 254 DEG C.
Elemental analysis (C21H18N2O3SSn): calculated value: C 50.73, H 3.65, N 5.63；Measured value: C 50.79, H
3.76, N 5.59.
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577,
1529, 1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854,
839, 802, 732, 694, 603, 563, 536, 453, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82
(m, 4H), 7.63 (d, J = 5.2 Hz, 1H), 7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07
(q, J = 7.6 Hz, 2H), 1.28 (t, J = 7.6 Hz, 3H)。
13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.85。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10)
Nm, c=2.0490 (2) nm, α=γ=90 °, β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, Dc=
1.575 Mg·m-3, m (MoK α)=1.342 mm-1, F (000)=992.
Embodiment 2:
The preparation of the one-dimensional chain stannous phenide complex of thienyl-containing ligand:
0.343g (1.0mmol) diphenyl stannous chloride, 0.145g (1.02mmol) 2- thiophene are added in microwave reaction tank
Formylhydrazine, 0.104g (1.02mmol) 2- batanone acid and 18mL solvent anhydrous methanol react 40 under conditions of temperature is 80 DEG C
Min is arranged the program cooling conditions of 3 DEG C/h, is down to 25 DEG C, obtains yellow transparent crystal, the as one-dimensional chain of thienyl-containing ligand
Shape stannous phenide complex.Yield: 87.4%.Fusing point: 252 ~ 254 DEG C.
Elemental analysis (C21H18N2O3SSn): calculated value: C 50.73, H 3.65, N 5.63；Measured value: C 50.79, H
3.76, N 5.59.
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577,
1529, 1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854,
839, 802, 732, 694, 603, 563, 536, 453, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82
(m, 4H), 7.63 (d, J = 5.2 Hz, 1H), 7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07
(q, J = 7.6 Hz, 2H), 1.28 (t, J = 7.6 Hz, 3H)。
13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.85。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10)
Nm, c=2.0490 (2) nm, α=γ=90 °, β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, Dc=
1.575 Mg·m-3, m (MoK α)=1.342 mm-1, F (000)=992.
Embodiment 3:
The preparation of the one-dimensional chain stannous phenide complex of thienyl-containing ligand:
0.248g (1.0mmol) diphenyl stannous chloride, 0.149g (1.05mmol) 2- thiophene are added in microwave reaction tank
Formylhydrazine, 0.110g (1.08mmol) 2- batanone acid and 22mL solvent anhydrous methanol react 70 under conditions of temperature is 70 DEG C
Min is arranged the program cooling conditions of 7 DEG C/h, is down to 25 DEG C, obtains yellow transparent crystal, the as one-dimensional chain of thienyl-containing ligand
Shape stannous phenide complex.Yield: 87.0%.Fusing point: 252 ~ 254 DEG C.
Elemental analysis (C21H18N2O3SSn): calculated value: C 50.73, H 3.65, N 5.63；Measured value: C 50.79, H
3.76, N 5.59.
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577,
1529, 1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854,
839, 802, 732, 694, 603, 563, 536, 453, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82
(m, 4H), 7.63 (d, J = 5.2 Hz, 1H), 7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07
(q, J = 7.6 Hz, 2H), 1.28 (t, J = 7.6 Hz, 3H)。
13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.85。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10)
Nm, c=2.0490 (2) nm, α=γ=90 °, β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, Dc=
1.575 Mg·m-3, m (MoK α)=1.342 mm-1, F (000)=992.
Embodiment 4:
The preparation of the one-dimensional chain stannous phenide complex of thienyl-containing ligand:
0.686g (2.0mmol) diphenyl stannous chloride, 0.291g (2.05mmol) 2- thiophene are added in microwave reaction tank
Formylhydrazine, 0.214g (2.10mmol) 2- batanone acid and 50mL solvent anhydrous methanol react under conditions of temperature is 120 DEG C
20 min are arranged the program cooling conditions of 1 DEG C/h, are down to 25 DEG C, obtain yellow transparent crystal, as thienyl-containing ligand is one-dimensional
Chain stannous phenide complex.Yield: 89.8%.Fusing point: 252 ~ 254 DEG C.
Elemental analysis (C21H18N2O3SSn): calculated value: C 50.73, H 3.65, N 5.63；Measured value: C 50.79, H
3.76, N 5.59.
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577,
1529, 1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854,
839, 802, 732, 694, 603, 563, 536, 453, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82
(m, 4H), 7.63 (d, J = 5.2 Hz, 1H), 7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07
(q, J = 7.6 Hz, 2H), 1.28 (t, J = 7.6 Hz, 3H)。
13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.85。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10)
Nm, c=2.0490 (2) nm, α=γ=90 °, β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, Dc=
1.575 Mg·m-3, m (MoK α)=1.342 mm-1, F (000)=992.
Embodiment 5:
The preparation of the one-dimensional chain stannous phenide complex of thienyl-containing ligand:
0.496g (2.0mmol) diphenyl stannous chloride, 0.293g (2.06mmol) 2- thiophene are added in microwave reaction tank
Formylhydrazine, 0.220g (2.16mmol) 2- batanone acid and 70mL solvent anhydrous methanol react 65 under conditions of temperature is 85 DEG C
Min is arranged the program cooling conditions of 17 DEG C/h, is down to 25 DEG C, obtains yellow transparent crystal, the as one-dimensional chain of thienyl-containing ligand
Shape stannous phenide complex.Yield: 85.2%.Fusing point: 252 ~ 254 DEG C.
Elemental analysis (C21H18N2O3SSn): calculated value: C 50.73, H 3.65, N 5.63；Measured value: C 50.79, H
3.76, N 5.59.
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577,
1529, 1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854,
839, 802, 732, 694, 603, 563, 536, 453, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82
(m, 4H), 7.63 (d, J = 5.2 Hz, 1H), 7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07
(q, J = 7.6 Hz, 2H), 1.28 (t, J = 7.6 Hz, 3H)。
13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.85。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10)
Nm, c=2.0490 (2) nm, α=γ=90 °, β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, Dc=
1.575 Mg·m-3, m (MoK α)=1.342 mm-1, F (000)=992.
Test example:
The one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention, Anticancer Activity in vitro measurement is to pass through MTT
What experimental method was realized.
MTT analytic approach:
It is with metabolism reduction 3- (4,5-Dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide
Basis.The bluish violet that succinate dehydrogenase in living cells mitochondria can make exogenous MTT be reduced to water-insoluble crystallizes first a ceremonial jade-ladle, used in libation
(Formazan) it and is deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell,
With the optical density of microplate reader measurement characteristic wavelength, it can reflect living cells quantity indirectly.
The one-dimensional chain stannous phenide complex of the thienyl-containing ligand of the preparation of embodiment 1 is measured using mtt assay to people
Colon cancer cell (Colo205), human liver cancer cell (HepG2), human breast cancer cell (MCF7), human cervical carcinoma cell (Hela)
With the inhibitory activity of human lung carcinoma cell (NCI-H460).
Cell strain and cultivating system: Colo205, HepG2, MCF7, Hela and NCI-H460 cell strain are derived from American tissue
Incubator (ATCC).With the RPMI 1640(GIBICO company for containing 10% fetal calf serum) culture medium, in 5%(volume fraction) CO2、
In vitro culture is carried out in 37 DEG C of saturated humidity incubators.
Test process: test medical fluid (0.1nM ~ 10uM) is added separately in each hole according to the concentration gradient of concentration,
Each concentration sets 6 parallel holes.Experiment is divided into drug study group (the test medicine for being separately added into various concentration), control group (only adds
Test medicine is not added in culture solution and cell) and blank group (only plus cultivating medicine, cell and test medicine is not added).By the orifice plate after dosing
37 DEG C are placed in, 5%CO272h is cultivated in incubator.The activity of control drug is measured according to the method for test sample.It is cultivating
In orifice plate after 72h, every hole adds MTT 40uL(to be made into 4mg/mL with D-Hanks buffer).After 37 DEG C of placement 4h, remove
Layer clear liquid.Every hole adds 150uL DMSO, vibrates 5min, makes Formazan crystallization dissolution.Finally, being existed using automatic microplate reader
The optical density in each hole is detected at 570nm wavelength.
Data processing: data processing uses 7.0 program of Graph Pad Prism version, complex IC50Pass through journey
Nonlinear regression model (NLRM) in sequence with S-shaped dose response is fitted to obtain.
The one-dimensional chain stannous phenide complex of the thienyl-containing ligand of each embodiment preparation is with MTT analytic approach to people's colon
Cancer cell (Colo205), human liver cancer cell (HepG2), human breast cancer cell (MCF7), human cervical carcinoma cell (Hela) and people
Lung carcinoma cell (NCI-H460) cell strain is analyzed, its IC is measured50Value, average result is as shown in table 1, conclusion are as follows: by table
Data are it is found that be used as anticancer drug with the one-dimensional chain stannous phenide complex of thienyl-containing ligand of the invention, to people's colon
Cancer cell (Colo205), human liver cancer cell (HepG2), human breast cancer cell (MCF7), human cervical carcinoma cell (Hela) and people
Lung carcinoma cell (NCI-H460) has certain drug effect, can be used as the candidate compound of anticancer drug.
The one-dimensional chain stannous phenide complex anticancer drug external activity test data of 1 thienyl-containing ligand of table.
Claims (10)
1. a kind of one-dimensional chain stannous phenide complex of thienyl-containing ligand is the complex of following structure formula (I):
(I)
Wherein R is phenyl.
2. the one-dimensional chain stannous phenide complex of thienyl-containing ligand as described in claim 1, ir data:
FT-IR (KBr, ν/cm-1): 3454, 3093, 3049, 2983, 2875, 1629, 1593, 1577, 1529,
1496, 1477, 1431, 1386, 1317, 1307, 1265, 1201, 1147, 1064, 1024, 854, 839,
802, 732, 694, 603, 563, 536, 453, 418；Its nuclear-magnetism modal data:1H NMR (500 MHz, CDCl3, δ/
ppm): 8.05 (d, J = 3.6 Hz, 1H), 7.80-7.82 (m, 4H), 7.63 (d, J = 5.2 Hz, 1H),
7.46-7.48 (m, 6H), 7.19-7.20 (m, 1H), 3.07 (q, J = 7.6 Hz, 2H), 1.28 (t, J =
7.6 Hz, 3H)；13C NMR (125 MHz, CDCl3, δ/ppm): 170.99, 163.32, 159.19, 136.37,
136.14, 135.61, 132.38, 132.20, 131.46, 129.42, 128.02, 21.18, 10.89；119Sn NMR
(187 MHz, CDCl3, δ/ppm): -294.85。
3. the one-dimensional chain stannous phenide complex of thienyl-containing ligand as described in claim 1, which is characterized in that described
The one-dimensional chain stannous phenide complex of thienyl-containing ligand is crystal structure, and crystallographic data is as follows: monoclinic system, space
Group P2 (1)/n, a=1.15889 (14) nm, b=0.89899 (10) nm, c=2.0490 (2) nm, α=γ=90 °,
β=100.885 (2) °, Z=4, V=2.0963 (4) nm3, the Mgm of Dc=1.575-3, m (MoK α)=1.342 mm-1, F
(000) = 992；Tin atom is hexa-coordinate distorted octahedron configuration in molecule, and the molecule constitutes one-dimensional nothing by Sn-O key
Limit chain structure.
4. the one-dimensional chain stannous phenide complex of thienyl-containing ligand described in claim 1, which is characterized in that have centainly
Thermostabilization range can be stabilized at 252 DEG C or less.
5. the preparation method of the one-dimensional chain stannous phenide complex of thienyl-containing ligand described in claim 1, it is characterized in that
Using microwave one pot process, diphenyl stannous chloride, 2- thenoyl hydrazine, 2- batanone acid and molten are added in microwave reaction tank
Agent anhydrous methanol reacts 10 ~ 100 min under conditions of temperature is 60 ~ 120 DEG C, and program is cooled to 25 DEG C, obtains yellow transparent crystalline substance
Body, as the one-dimensional chain stannous phenide complex of thienyl-containing ligand.
6. preparation method as claimed in claim 5, which is characterized in that the diphenyl stannous chloride, 2- thenoyl hydrazine, 2-
The mass ratio of the material of batanone acid three is 1:(1 ~ 1.05): (1 ~ 1.1).
7. preparation method as claimed in claim 5, which is characterized in that the solvent anhydrous methanol dosage is every mM of hexichol
Base stannous chloride adds 5 ~ 35 milliliters.
8. preparation method as claimed in claim 5, which is characterized in that described program cooling conditions are 0.1 ~ 20 DEG C/h.
9. the one-dimensional chain stannous phenide complex of thienyl-containing ligand described in claim 1 is preparing answering in anticancer drug
With.
10. application as claimed in claim 9, wherein the cancer cell of the application is human colon cancer cell, human liver cancer cell, human milk
Adenocarcinoma cell, human cervical carcinoma cell, human lung carcinoma cell.
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