CN111057098A - Preparation method and application of tri (2-methyl-2 phenylpropyl) tin 1-naphthoate complex - Google Patents
Preparation method and application of tri (2-methyl-2 phenylpropyl) tin 1-naphthoate complex Download PDFInfo
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- OFNRQJCVUCSFAR-UHFFFAOYSA-M tris(2-methyl-2-phenylpropyl)stannyl naphthalene-1-carboxylate Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)[O-].CC(C[Sn+](CC(C)(C)C1=CC=CC=C1)CC(C)(C)C1=CC=CC=C1)(C)C1=CC=CC=C1 OFNRQJCVUCSFAR-UHFFFAOYSA-M 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 18
- FIDXVVHZWRFINX-UHFFFAOYSA-N tris(2-methyl-2-phenylpropyl)tin Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 FIDXVVHZWRFINX-UHFFFAOYSA-N 0.000 claims description 14
- 229910001887 tin oxide Inorganic materials 0.000 claims description 13
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 12
- 201000005202 lung cancer Diseases 0.000 claims description 12
- 208000020816 lung neoplasm Diseases 0.000 claims description 12
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 10
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 10
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 10
- 201000010881 cervical cancer Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 206010017758 gastric cancer Diseases 0.000 claims description 10
- 201000011549 stomach cancer Diseases 0.000 claims description 10
- 230000001093 anti-cancer Effects 0.000 claims description 9
- 238000000902 119Sn nuclear magnetic resonance spectroscopy Methods 0.000 claims description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000002447 crystallographic data Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- XTTBHNHORSDPPN-UHFFFAOYSA-J naphthalene-1-carboxylate;tin(4+) Chemical compound [Sn+4].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 XTTBHNHORSDPPN-UHFFFAOYSA-J 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 abstract description 11
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 11
- 210000004027 cell Anatomy 0.000 description 30
- 238000012360 testing method Methods 0.000 description 9
- 229910052718 tin Inorganic materials 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- -1 tin carboxylate Chemical class 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 5
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
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- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- FBIVKLDWLAMJMB-UHFFFAOYSA-N propyltin Chemical compound CCC[Sn] FBIVKLDWLAMJMB-UHFFFAOYSA-N 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000000134 MTT assay Methods 0.000 description 1
- 231100000002 MTT assay Toxicity 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
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- 238000012417 linear regression Methods 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical class [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001942 tin-119 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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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 Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
-
- 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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- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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Abstract
The invention discloses a preparation method and application of a tri (2-methyl-2-phenylpropyl) tin 1-naphthoate complex, which is a complex with the following structural formula (I)
. The invention also discloses a preparation method of the tri (2-methyl-2 phenyl propyl) tin 1-naphthoate complex and application of the complex in preparing antitumor drugs.
Description
Technical Field
The invention relates to a tri (2-methyl-2 phenylpropyl) tin 1-naphthoate complex, a preparation method thereof and application of the complex in preparing an anti-tumor medicament.
Background
The organic tin carboxylate has high bioactivity and wide application prospect in the fields of sterilization, insecticide, anti-cancer drug preparation and the like, so that research on synthesis, structure and bioactivity of organic tin carboxylate complexes is widely concerned by scientists. The existing research shows that the alkyl R in the organotin carboxylate is the main factor for determining the anticancer activity of the compound, for example, cyclohexyl, n-butyl and phenyl tin compounds have stronger anticancer activity, and ethyl has almost no anticancer activity, and the known organotin compounds generally have stronger toxicity, so the application is limited. Regulating the balance between toxicity and biological activity is an important direction of research. The functional activation of alkyl or ligand can greatly change the coordination mode of tin atom, and further influence the bioactivity of organic tin complex. Research shows that the toxicity of the organic tin compound is related to the relative molecular mass of the organic tin compound, the smaller the relative molecular mass is, the greater the toxicity is, and the larger the relative molecular mass of the large steric hindrance alkyl tin. Therefore, the novel large steric hindrance alkyl tin carboxylate complex is synthesized, and the structure and the biological activity of the complex are researched, so that the complex has important research significance.
The bis [ tris (2-methyl-2-phenylpropyl) tin ] carboxylate disclosed in european patent EP0177785B1 has stronger biological activity than bis [ tris (2-methyl-2-phenylpropyl) tin ] oxide.
Chinese patent CN 106279256B discloses the application of bis [ tris (2-methyl-2-phenyl) propyl tin ]2, 2' -biphenyl diformate complex in the preparation of drugs for treating lung cancer, breast cancer and liver cancer.
Chinese patent CN 106279253B discloses the application of bis [ tris (2-methyl-2-phenyl) propyl tin ] 5-nitroisophthalate complex in the preparation of drugs for treating lung cancer, breast cancer and liver cancer.
Based on that the bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide is a substance with better biological activity proved by experiments, and the 2-methyl-2-phenylpropyl has the characteristics of larger steric hindrance, larger molecular weight and the like, the invention selects the bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide to react with the ligand 1-naphthoic acid under certain conditions to synthesize the complex with stronger inhibitory activity to A549 (human lung cancer cells), Hela (human cervical cancer cells) and HGC-27 (human gastric cancer cells), and provides a new way for developing anticancer drugs.
Disclosure of Invention
In view of the problems of the prior art, the first object of the present invention is to provide a tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex.
It is a second object of the present invention to provide a process for preparing the above tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex.
The third purpose of the invention is to provide the application of the tri (2-methyl-2 phenyl propyl) tin 1-naphthoate complex in preparing anticancer drugs.
A tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex as a first aspect of the present invention has the following structural formula (I):
(I)。
the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex of the invention is analyzed by element analysis, infrared spectrum analysis, nuclear magnetic resonance spectrum and X-ray single crystal structure, and the result is as follows:
elemental analysis (C)41H46O2Sn): theoretical value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex is of a crystal structure, and the crystallographic data thereof are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9) nm，c=2.34486(14)nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
the tri (2-methyl-2 phenyl propyl) tin 1-naphthoate complex has the structural characteristics that: the central tin in the molecule forms a distorted tetrahedral configuration with the coordinating atoms.
In the second aspect of the present invention, a preparation method of a tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex is provided, wherein bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 1-naphthoic acid and solvent anhydrous methanol are sequentially added to a microwave reaction tank in sequence, and a microwave reaction is performed at an irradiation power of 800W and a temperature of 100 ℃ in an air atmosphere for a period of 60 to 120 min. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex.
In a preferred embodiment of the invention, the mass ratio of the bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide to the 1-naphthoic acid is 1 (2-2.1).
In a preferred embodiment of the present invention, the solvent is anhydrous methanol in an amount of 10 to 15 ml per mmol of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide.
The third aspect of the invention relates to the application of a tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex in preparing an anticancer drug.
The applicant carries out in-vitro antitumor activity confirmation research on the complex, and confirms that the complex has certain antitumor biological activity, namely the application of the complex in preparing antitumor drugs, in particular in preparing anti-human lung cancer drugs, human cervical cancer drugs and human gastric cancer drugs.
The tri (2-methyl-2 phenyl propyl) tin 1-naphthoate complex shows good anticancer activity on human lung cancer cells, human cervical cancer cells, human gastric cancer cells and the like, and can be used as a raw material for preparing anti-lung cancer, anti-cervical cancer and anti-gastric cancer medicines. Compared with the currently commonly used platinum anticancer drugs, the tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex has the characteristics of high anticancer activity, low cost, simple preparation method and the like, and provides a new way for developing anticancer drugs.
Drawings
FIG. 1 is a crystal molecular structural diagram of a tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex.
FIG. 2 is an IR spectrum of tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex.
FIG. 3 is a drawing showing a tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex1H NMR spectrum.
FIG. 4 is a drawing showing a tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex13C NMR spectrum.
FIG. 5 is a drawing showing a tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex119Sn NMR spectrum.
Detailed Description
The present invention is further illustrated in detail by the following examples, but it should be noted that the scope of the present invention is not limited by these examples at all.
Example 1:
preparation of tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex:
the method comprises the steps of sequentially adding 1.0536 g (1mmol) of bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide, 0.3452 g (2 mmol) of 1-naphthoic acid and 10 mL of solvent anhydrous methanol into a microwave reaction tank, and carrying out microwave reaction at 100 ℃ for 60 min under the air atmosphere at the radiation power of 800W. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex. Yield: 77%, melting point: 87-89 ℃.
Elemental analysis (C)41H46O2Sn): theoretical value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The crystallographic data are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9)nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
example 2:
preparation of tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex:
1.053 g (1.0mmol) of tin bis [ tris (2-methyl-2-phenylpropyl) ] oxide, 0.3630 g (2.1 mmol) of 1-naphthoic acid and 15 mL of solvent anhydrous methanol are sequentially added into a microwave reaction tank, and microwave reaction is carried out at the radiation power of 800W and the temperature of 100 ℃ for 60 min under the air atmosphere. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex. Yield: 78%, melting point: 87-89 ℃.
Elemental analysis (C)41H46O2Sn): theoretical value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The crystallographic data are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9)nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
example 3:
preparation of tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex:
1.0534 g (1mmol) of bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide, 0.3450 g (2 mmol) of 1-naphthoic acid and 12 mL of solvent anhydrous methanol are sequentially added into a microwave reaction tank, and microwave reaction is carried out at the radiation power of 800W and the temperature of 100 ℃ for 120min under the air atmosphere. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex. Yield: 79%, melting point: 87-89 ℃.
Elemental analysis (C)41H46O2Sn): theoretical value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The crystallographic data are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9)nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
example 4:
preparation of tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex:
2.1038 g (2.0mmol) of bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide, 0.6914g (4 mmol) of 1-naphthoic acid and 25mL of solvent anhydrous methanol are sequentially added into a microwave reaction tank, and microwave reaction is carried out at the radiation power of 800W and the temperature of 100 ℃ for 60 min under the air atmosphere. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex. Yield: 76%, melting point: 87-89 ℃.
Elemental analysis (C)41H46O2Sn): theoretical value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H),7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The crystallographic data are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9)nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
example 5:
preparation of tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex:
2.1036 g (2.0mmol) of bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide, 0.7077 g (4.1 mmol) of 1-naphthoic acid and 25mL of solvent anhydrous methanol are sequentially added into a microwave reaction tank, and microwave reaction is carried out at the radiation power of 800W and the temperature of 100 ℃ for 90 min under the air atmosphere. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex. Yield: 79%, melting point: 87-89 ℃.
Elemental analysis (C)41H46O2Sn): theory of the inventionThe value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The crystallographic data are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9)nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
example 6:
preparation of tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex:
the method comprises the steps of sequentially adding 3.15933 g (3mmol) of bis [ tri (2-methyl-2-phenylpropyl) ] tin oxide, 1.0360 g (6 mmol) of 1-naphthoic acid and 30 mL of solvent anhydrous methanol into a microwave reaction tank, and carrying out microwave reaction at 100 ℃ for 120min under the air atmosphere at the radiation power of 800W. After the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex. Yield: 78%, melting point: 87-89 ℃.
Elemental analysis (C)41H46O2Sn): theoretical value: c, 71.42; h, 6.72. Measurement value: c, 71.48; h, 6.75.
IR(KBr, v/cm-1): 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m)。
1H NMR (CDCl3, 500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7Hz, 1H), 7.98(d,J= 7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H),7.54-7.47 (m, 2H), 7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H),1.41-1.16(m, 24H)。
13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59,130.58, 129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32,124.63, 37.77, 37.60, 32.85。
119Sn NMR(CDCl3, 186 MHz), δ(ppm): 89.58。
The crystallographic data are as follows: the crystal belongs to monoclinic system and space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9)nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3，Dc=1.273 Mg·m-3，μ(MoKa)= 0.742mm-1，F(000)= 1432，2.18°＜θ< 25.01 °, crystal size: 0.24X 0.22X 0.20 mm,R=0.0318，wR=0.0869。
test example:
the in vitro anticancer activity of the tri (2-methyl-2 phenyl propyl) tin 1-naphthoate complex is determined by an MTT experimental method.
MTT assay:
based on the metabolic reduction of 3- (4, 5-dimethylthiozol-2-yl) -2, 5-diaryltetrazolium bromide. Succinate dehydrogenase in mitochondria of living cells can reduce exogenous MTT to water-insoluble blue-purple crystalline Formazan (Formazan) and deposit in cells, while dead cells do not have this function. Dimethyl sulfoxide (DMSO) can dissolve formazan in cells, and the optical density of characteristic wavelength is measured by enzyme labeling instrument, which can indirectly reflect the number of living cells.
The inhibitory activity of the tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex prepared in example 1 on human lung cancer cells (a 549), human cervical cancer cells (Hela), and human gastric cancer cells (HGC-27) was determined by the MTT method.
Cell line and culture System: the A549, Hela and HGC-27 cell lines were obtained from the American tissue culture Bank (ATCC). Using RPMI1640 medium (GIBICO) containing 10% fetal bovine serum at 5% (volume fraction) CO2And culturing in vitro in a 37 ℃ saturated humidity incubator.
The testing process comprises the following steps: and respectively adding the test liquid medicine (0.0625-0.5 mu mol/L) into each hole according to the concentration gradient of the concentration, wherein each concentration is provided with 3 parallel holes. The experiment was divided into drug test group (with different concentrations of test drug added), control group (with culture medium and cells only, without test drug added) and blank group (with culture medium only, without cells and test drug added). Placing the medicated hole plate at 37 deg.C and 5% CO2Culturing in an incubator for 24 h. The activity of the control drug was determined as per the method of the test sample. In the well plate after 48 hours of incubation, 20uL of MTT (5 g/L in PBS) was added to each well. After standing at 37 ℃ for 4h, the supernatant was removed. Add 150uL DMSO to each well, shake for 10min to dissolve the Formazan crystals. Finally, the absorbance of each well was measured at a wavelength of 570nm using a BioTek multifunctional microplate reader.
Data processing: data processing was performed using the GraAr Pad Prism version5.0 program,complex IC50Fitting was done by a non-linear regression model with sigmoidal dose response in the program.
Analyzing human lung cancer cell (A549) cell line, human cervical cancer cell (Hela) cell line and human gastric cancer cell (HGC-27) cell line by MTT analysis method, and determining IC50The results are shown in table 1, with the conclusion that: as can be seen from the data in the table, the tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex has high anticancer activity on human lung cancer, human cervical cancer and human gastric cancer as an anticancer drug, and can be used as a candidate complex of the anticancer drug.
Table 1 tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex anticancer drug in vitro activity test data.
| Human lung cancer cell | Human cervical cancer cell | Human gastric cancer cell | |
| Cell line | A549 | Hela | HGC-27 |
| IC50μM | 0.6928 | 0.8059 | 0.4952 |
The tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex prepared in the remaining examples was tested for anticancer activity against human lung cancer cells (a 549), human cervical cancer cells (Hela) and human gastric cancer cells (HGC-27) by MTT method in the same experimental example, and the test results were substantially the same as in table 1.
Claims (8)
1. A tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex is a complex of the following structural formula (I):
(I)。
2. the tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex as claimed in claim 1 having an infrared spectrum data of: FT-IR (KBr, v/cm)-1) 3053.32(m), 2962.66(s), 2922.16(m), 1641.42(s),1539.20(m), 1494.83(s) 1462.04(m), 1442.75(s), 1382.96(m), 1363.67(m),1325.10(m),1301.95(s), 1276.88(m), 1253.73(m), 1190.08(m), 1141.86(m),1109.07(w), 1074.35(s),1029.99(m), 1001.06(m), 972.12(w), 927.76(w), 867.97(m), 817.82(w), 785.03(s), 767.67(s), 740.67(m), 698.32(s), 657.73(m), 617.22(m), 553.57(m), 509.21(m), 491.85(m), 437.84(m), and its nuclear magnetic spectrum data:1H NMR (CDCl3,500 MHz)δ(ppm): 9.03 (d,J= 8.5 Hz, 1H), 8.09(d,J= 7 Hz, 1H), 7.98(d,J=7.5 Hz, 1H), 7.89(d,J= 8 Hz, 1H), 7.62-7.59 (m, 1H), 7.54-7.47 (m, 2H),7.32-7.29 (m, 7H),7.26-7.21(m, 4H), 7.16-7.15 (m, 4H), 1.41-1.16(m, 24H);13CNMR(CDCl3, 125MHz)δ(ppm): 172.04, 150.96, 133.85, 131.94, 131.59, 130.58,129.98, 128.36, 128.28, 126.96, 126.65, 125.83, 125.74,125.32, 124.63, 37.77,37.60, 32.85;119Sn NMR (CDCl3，186 MHz),δ(ppm): 89.58。
3. the tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex as claimed in claim 1, wherein the tris (2-methyl-2-benzene)Propyl) tin 1-naphthoate complex is of a crystal structure, and the crystallographic data are as follows: monoclinic system, space groupP 2 1 /c，a=0.98489(6) nm，b=1.5619(9) nm，c=2.34486(14) nm，α=90°，β=94°，γ=90°，Z=4，V=3.5968(4) nm3(ii) a The central tin in the molecule forms a distorted tetrahedral configuration with the coordinating atoms.
4. The preparation method of the tris (2-methyl-2-phenylpropyl) tin 1-naphthoate complex as claimed in claim 1, characterized in that bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide, 1-naphthoic acid and solvent anhydrous methanol are sequentially added into a microwave reaction tank in order, and microwave reaction is carried out at a radiation power of 800W and a temperature of 100 ℃ for a period of 60 to 120min under an air atmosphere; after the reaction is finished, naturally cooling, filtering, and naturally volatilizing the solvent at room temperature to crystallize to obtain a white crystal, namely the tris (2-methyl-2 phenyl propyl) tin 1-naphthoate complex.
5. The method according to claim 4, wherein the mass ratio of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide to 1-naphthoic acid is 1 (2 to 2.1).
6. The method according to claim 4, wherein the solvent is 10 to 15 ml of anhydrous methanol per mmol of bis [ tris (2-methyl-2-phenylpropyl) ] tin oxide.
7. Use of the tris (2-methyl-2 phenylpropyl) tin 1-naphthoate complex of claim 1 in the preparation of an anti-cancer medicament.
8. The use of claim 7, wherein the cancer cell is lung cancer, cervical cancer, gastric cancer.
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| CN110128466A (en) * | 2019-05-31 | 2019-08-16 | 衡阳师范学院 | Three (2- methyl -2- phenyl) propyl tin 3- indolebutyric acid ester complexs of one kind and preparation method and application |
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| CN110128466A (en) * | 2019-05-31 | 2019-08-16 | 衡阳师范学院 | Three (2- methyl -2- phenyl) propyl tin 3- indolebutyric acid ester complexs of one kind and preparation method and application |
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