CN106432322A - 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof - Google Patents
2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof Download PDFInfo
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- CN106432322A CN106432322A CN201610715774.1A CN201610715774A CN106432322A CN 106432322 A CN106432322 A CN 106432322A CN 201610715774 A CN201610715774 A CN 201610715774A CN 106432322 A CN106432322 A CN 106432322A
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- carbonyl
- phenylacetic acid
- nitrophenyl formyl
- coordination compound
- stannous phenide
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- -1 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin Chemical compound 0.000 title claims abstract description 14
- 238000010668 complexation reaction Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 53
- JEVZLYAIIMSQOF-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)N(N=C(C(C1=CC=CC=C1)=C=O)O)C=O Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N(N=C(C(C1=CC=CC=C1)=C=O)O)C=O JEVZLYAIIMSQOF-UHFFFAOYSA-N 0.000 claims description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 206010006187 Breast cancer Diseases 0.000 claims description 11
- 208000026310 Breast neoplasm Diseases 0.000 claims description 11
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- FKZXYJYTUSGIQE-UHFFFAOYSA-N 4-nitrobenzohydrazide Chemical compound NNC(=O)C1=CC=C([N+]([O-])=O)C=C1 FKZXYJYTUSGIQE-UHFFFAOYSA-N 0.000 claims description 8
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
- 201000007270 liver cancer Diseases 0.000 claims description 8
- 208000014018 liver neoplasm Diseases 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- VTESCYNPUGSWKG-UHFFFAOYSA-N (4-tert-butylphenyl)hydrazine;hydrochloride Chemical compound [Cl-].CC(C)(C)C1=CC=C(N[NH3+])C=C1 VTESCYNPUGSWKG-UHFFFAOYSA-N 0.000 claims description 6
- 238000000902 119Sn nuclear magnetic resonance spectroscopy Methods 0.000 claims description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 6
- 201000005296 lung carcinoma Diseases 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000002447 crystallographic data Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 239000003005 anticarcinogenic agent Substances 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- FSQMMQKZAJETGN-UHFFFAOYSA-N n-amino-n-(4-nitrophenyl)formamide Chemical compound O=CN(N)C1=CC=C([N+]([O-])=O)C=C1 FSQMMQKZAJETGN-UHFFFAOYSA-N 0.000 claims 1
- 230000005311 nuclear magnetism Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 20
- 230000001093 anti-cancer Effects 0.000 abstract description 13
- 229940079593 drug Drugs 0.000 abstract description 12
- 210000004027 cell Anatomy 0.000 description 38
- 238000011160 research Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000011275 oncology therapy Methods 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 206010009944 Colon cancer Diseases 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 208000029742 colonic neoplasm Diseases 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 201000005249 lung adenocarcinoma Diseases 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 201000008275 breast carcinoma Diseases 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 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 3
- 241000699670 Mus sp. Species 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 229910020813 Sn-C Inorganic materials 0.000 description 1
- 229910018732 Sn—C Inorganic materials 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 201000001514 prostate carcinoma Diseases 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000001942 tin-119 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- 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
- C07F7/2284—Compounds with one or more Sn-N linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a 2-carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex. The complex is represented by structural formula (I); and Ph in the structural formula (I) is a phenyl group. The invention also discloses a preparation method of the 2-carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and an application of the complex in the preparation of anticancer medicines.
Description
Technical field
The present invention relates to a kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound and its preparation side
Method, and the application of the 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound in cancer therapy drug is prepared.
Background technology
Organotin is the metallo-organic compound that a class contains Sn-C key.Researcher was just noticed before very early
The Anticancer Activity in vitro of organo-tin compound.The research of organotin (IV) antitumor activity of compound can trace back to nineteen twenty-nine.
1967, Kanisawa etc. thought that stannic chloride is invalid to the primary tumor of mice and rat.But in 1972, Brown had found,
By food or drug administration by injection, triphenyltin acetate Ph3SnOOCCH3Can suppress the tumour growth of mice, and triphenyltin chloride
Then can not.Between 1972 ~ 1977 years, the substantial amounts of organo-tin compound of Dutch scholar's research, but find no screening valency further
The compound of value.They continue deeper into research, finally found that the tin compound of two organic group coordinations, such as tin-oxide
(R2SnO), stannum hydroxide ［ SnR2(OH) X ］ etc. have an anti-tumor activity, and find out that they all contain or hydrolyze and can produce stannum oxygen
Key.1980, Crowe etc. was found that some organo-tin compounds have preferable active anticancer again, from this, anti-with regard to organotin
The research of cancer activity becomes the another focus for extremely enlivening after cisplatin.1989, American National anticancer research institute
(National Cancer Institute) has carried out antitumor activity screening to more than 2,000 kinds of organo-tin compounds, as a result table
Some organo-tin compounds bright have inhibitory action to P388 Lymphocytic leukemia.2002, Gielen et al. was to organic
The activity of stannum carboxylate compound has done comprehensive summing up, thinks that many organo-tin compounds have really preferably external after research
Active anticancer.
Research shows, the organic group for connecting on organic tin atom and the part for participating in coordination decide organo-tin compound
Biological activity, select some itself there are organic ligands of good biological activity cause with the tin atom coordination in organotin
The great interest of people.Acylhydrazone be by a class Schiff compound of hydrazide kind compound modification, they
Formed by aldehydes or ketones and hydrazides condensation, with the of bonding similar with peptide bond in molecule, with good biological activity, stronger join
Capability and various coordination mode, and have a wide range of applications at the aspect such as medicine, pesticide, material and analytical reagent.Closely
Nian Lai, both at home and abroad many research worker which is compared in terms of biological activity and is in depth studied, research find acylhydrazone class
Compound has the various active such as anticancer, sterilization, antiinflammatory.Therefore, acylhydrazone class Schiff part is combined with organotin, it is intended to
The higher noval chemical compound of biological activity is obtained, becomes people's research direction interested.
Chinese patent CN 102718794A discloses a kind of pair of acylhydrazone class Schiff stannous phenide coordination compound and its in system
Application in standby Antilung gland cancer, colon cancer, the medicine of leukaemia.
Chinese patent CN 101851251A disclose a kind of dibutyl tin coordination compound of acylhydrazone class Schiff part and its
Application in treatment hepatocarcinoma, adenocarcinoma of lung, breast carcinoma, carcinoma of prostate, colon cancer or the leukemic medicine of early children's grain is prepared.
Document (Journal of Organometallic Chemistry, 2014,75:83-91) report, organotin
Acylhydrazone class Schiff base complex is thin to human colon cancer cell (HCT-116), human lung adenocarcinoma cell (A549), human umblilical vein endothelial
Born of the same parents (HUVEC) have compared with strong biological activity, and are better than carboplatin.
Document (Journal of Organometallic Chemistry, 2013,724:23-31) report, series has
Machine stannum acylhydrazone class Schiff base complex, organo-tin compound and acylhydrazone class Schiff part are respectively to human lung adenocarcinoma cell
(A549), the inhibitory action of the cancerous cell such as human colon cancer cell (HCT-8), people in loop (hl-60).
Document (Bioorganic ＆ Medicinal Chemistry Letters, 2015,25: 4461- 4463)
Report, multiple acylhydrazone class Schiff parts are to human liver cancer cell (HuH-7) and the active anticancer of human lung adenocarcinoma cell (A549).
Document (Journal of Organometallic Chemistry, 2016,804:48-58) report, two hydrocarbon
Base stannum acylhydrazone class Schiff base complex is to human lung adenocarcinoma cell (A549), human cervical carcinoma cell (HeLa), human breast cancer cell
(MCF-7) inhibitory action of cancerous cell such as.
It is to the experiment proved that the material with active anticancer based on acylhydrazone class Schiff organotin complex, the present invention is selected
Select p-nitrobenzoylhydrazide, benzoyl formic acid and diphenyl stannum dichloride to react under certain condition, synthesis has been obtained to people's lung
The coordination compound of cancerous cell (H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) with certain inhibitory activity, be
Exploitation cancer therapy drug provides new approach.
Content of the invention
The first object of the present invention there is provided a kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide and join
Compound.
The second object of the present invention is to provide above-mentioned 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide to coordinate
Thing preparation method.
The third object of the present invention is to provide above-mentioned 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide to coordinate
Application of the thing in cancer therapy drug is prepared.
A kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide as a first aspect of the present invention coordinates
Thing, is the coordination compound of structure formula (I)
(I)
Wherein Ph is phenyl.
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide the coordination compound of the present invention is through elementary analysiss, infrared
Spectrum, nuclear magnetic resoance spectrum and X-ray single crystal diffraction structural analyses, as a result as follows：
Elementary analysiss (C108H76N12O20Sn4)：Value of calculation：C 55.51, H 3.28, N 7.19；Measured value：C 55.55, H
3.27, N 7.18.
FT-IR (KBr, ν/cm-1): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600,
1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 852,
817, 734, 719, 690, 590, 547, 451, 410.
1H NMR (500 MHz, CDCl3, δ/ppm): 8.44 (d,J= 8.8 Hz, 2H), 8.34 (d,J=
8.8 Hz, 2H), 8.15-8.18 (m, 2H), 7.86-7.88 (m, 4H), 7.50-7.59 (m, 9H).
13C NMR (126 MHz, CDCl3, δ/ppm): 173.24, 162.53, 152.49, 150.28,
137.91, 136.11, 135.35, 132.47, 132.44, 131.71, 129.75, 129.60, 127.99,
127.86, 123.65.
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.09.
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide the coordination compound of the present invention is crystal structure, and which is brilliant
Body is：Anorthic system, space group P-1, a=1.3060 (3) nm, b=1.4029 (3) nm, c=1.4469 (3) nm, α=
96.280 (3) °, β=106.826 (3) °, γ=94.816 (3) °, 2.5037 (10) nm of Z=2, V=3, Dc=1.550
Mg·m-3, m (MoK α)=1.063 mm-1, F (000)=1168.
Being structurally characterized in that of the 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound of the present invention：Point
In son, tin atom is hexa-coordinate distorted octahedron configuration.
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide the coordination compound of the present invention has certain thermally-stabilised
Scope, can stable existence below 276 DEG C.
A kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide as a second aspect of the present invention coordinates
The preparation method of thing, adds diphenyl stannum dichloride, p-nitrobenzoylhydrazide, benzoyl in the reaction vessel for having nitrogen protection
Formic acid and 95% methanol of solvent, react 5 ~ 24 h under conditions of temperature is 45 ~ 65 DEG C, cool down, filter, in 20 ~ 35 DEG C of condition
Lower control solvent volatilization crystallization, obtains yellow transparent crystal, as 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide
Coordination compound.
The preparation characteristic of the 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound of the present invention is：From
The relatively easy raw material being easy to get sets out, and without the separation of intermediate, directly obtains baroque molecule, i.e. one kettle way；So
Reaction economically and environmentally close friend on advantageously.
In a preferred embodiment of the invention, the diphenyl stannum dichloride, p-nitrobenzoylhydrazide, benzoyl first
The amount ratio of the material of sour three is 1:(1~1.05):(1.05~1.15).
In a preferred embodiment of the invention, 95% methanol usage of the solvent is per mM of diphenyl dichloride
Stannum adds 15 ~ and 35 milliliters.
A kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide as a third aspect of the present invention coordinates
Application of the thing in cancer therapy drug is prepared.
Applicant has carried out external anti-to above-mentioned 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound
Cancer activity determines research, it is thus identified that 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound has certain
Anticancer bioactive, that is to say, that the purposes of above-mentioned coordination compound is the application in cancer therapy drug is prepared, be exactly specifically
Prepare the application in anti-human pulmonary carcinoma, human liver cancer and human breast carcinoma medicine.
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide the coordination compound of the present invention is to human lung carcinoma cell, people
Hepatoma carcinoma cell and human breast cancer cell show good active anticancer, the 2- carbonyl -2- phenylacetic acid p-nitrophenyl of the present invention
The features such as formyl hydrazone stannous phenide coordination compound active anticancer height, low cost, preparation method are simple, is that the new cancer therapy drug of exploitation is carried
New way is supplied.
Description of the drawings
Fig. 1 is the IR spectrogram of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.
Fig. 2 is 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound1H NMR spectra.
Fig. 3 is 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound13C NMR spectra.
Fig. 4 is 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound119Sn NMR spectra.
Fig. 5 is the crystal structure figure of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.
Fig. 6 is the TG-DTG curve of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.
Specific embodiment
By detailed description below, the present invention is described in further detail.
Embodiment 1：
The preparation of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound：
0.344g (1.0mmol) diphenyl stannum dichloride, 0.181g is added in the 100mL there-necked flask for having nitrogen protection
(1.0mmol) p-nitrobenzoylhydrazide, 0.165g (1.1mmol) benzoyl formic acid and 95% methanol of 15mL solvent, in temperature be
8 h are reacted under conditions of 45 ~ 65 DEG C, cooling, filter, control solvent volatilization crystallization under conditions of 20 ~ 35 DEG C, obtain yellow transparent
Crystal, as 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.Yield：87.6%.Fusing point：276~
278℃(dec).
Elementary analysiss (C108H76N12O20Sn4)：Value of calculation：C 55.51, H 3.28, N 7.19；Measured value：C 55.55, H
3.27, N 7.18.
FT-IR (KBr, ν/cm-1): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600,
1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 852,
817, 734, 719, 690, 590, 547, 451, 410.
1H NMR (500 MHz, CDCl3, δ/ppm): 8.44 (d,J= 8.8 Hz, 2H), 8.34 (d,J=
8.8 Hz, 2H), 8.15-8.18 (m, 2H), 7.86-7.88 (m, 4H), 7.50-7.59 (m, 9H).
13C NMR (126 MHz, CDCl3, δ/ppm): 173.24, 162.53, 152.49, 150.28,
137.91, 136.11, 135.35, 132.47, 132.44, 131.71, 129.75, 129.60, 127.99,
127.86, 123.65.
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.09.
Crystallographic data：Anorthic system, space group P-1, a=1.3060 (3) nm, b=1.4029 (3) nm, c=
1.4469 (3) nm, α=96.280 (3) °, β=106.826 (3) °, γ=94.816 (3) °, Z=2, V=2.5037 (10)
nm3, 1.550 Mg m of Dc=-3, m (MoK α)=1.063 mm-1, F (000)=1168.
Embodiment 2：
The preparation of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound：
0.344g (1.0mmol) diphenyl stannum dichloride, 0.181g is added in the 100mL there-necked flask for having nitrogen protection
(1.0mmol) p-nitrobenzoylhydrazide, 0.157g (1.05mmol) benzoyl formic acid and 95% methanol of 35mL solvent, in temperature be
5 h are reacted under conditions of 45 ~ 65 DEG C, cooling, filter, control solvent volatilization crystallization under conditions of 20 ~ 35 DEG C, obtain yellow transparent
Crystal, as 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.Yield：89.5%.Fusing point：276~
278℃(dec).
Elementary analysiss (C108H76N12O20Sn4)：Value of calculation：C 55.51, H 3.28, N 7.19；Measured value：C 55.55, H
3.27, N 7.18.
FT-IR (KBr, ν/cm-1): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600,
1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 852,
817, 734, 719, 690, 590, 547, 451, 410.
1H NMR (500 MHz, CDCl3, δ/ppm): 8.44 (d,J= 8.8 Hz, 2H), 8.34 (d,J=
8.8 Hz, 2H), 8.15-8.18 (m, 2H), 7.86-7.88 (m, 4H), 7.50-7.59 (m, 9H).
13C NMR (126 MHz, CDCl3, δ/ppm): 173.24, 162.53, 152.49, 150.28,
137.91, 136.11, 135.35, 132.47, 132.44, 131.71, 129.75, 129.60, 127.99,
127.86, 123.65.
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.09.
Crystallographic data：Anorthic system, space group P-1, a=1.3060 (3) nm, b=1.4029 (3) nm, c=
1.4469 (3) nm, α=96.280 (3) °, β=106.826 (3) °, γ=94.816 (3) °, Z=2, V=2.5037 (10)
nm3, 1.550 Mg m of Dc=-3, m (MoK α)=1.063 mm-1, F (000)=1168.
Embodiment 3：
The preparation of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound：
0.344g (1.0mmol) diphenyl stannum dichloride, 0.190g is added in the 100mL there-necked flask for having nitrogen protection
(1.05mmol) p-nitrobenzoylhydrazide, 0.173g (1.15mmol) benzoyl formic acid and 95% methanol of 25mL solvent, in temperature
For reacting 24 h under conditions of 45 ~ 65 DEG C, cooling, filter, control solvent volatilization crystallization under conditions of 20 ~ 35 DEG C, obtain yellow
Transparent crystal, as 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.Yield：89.7%.Fusing point：
276~278℃(dec).
Elementary analysiss (C108H76N12O20Sn4)：Value of calculation：C 55.51, H 3.28, N 7.19；Measured value：C 55.55, H
3.27, N 7.18.
FT-IR (KBr, ν/cm-1): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600,
1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 852,
817, 734, 719, 690, 590, 547, 451, 410.
1H NMR (500 MHz, CDCl3, δ/ppm): 8.44 (d,J= 8.8 Hz, 2H), 8.34 (d,J=
8.8 Hz, 2H), 8.15-8.18 (m, 2H), 7.86-7.88 (m, 4H), 7.50-7.59 (m, 9H).
13C NMR (126 MHz, CDCl3, δ/ppm): 173.24, 162.53, 152.49, 150.28,
137.91, 136.11, 135.35, 132.47, 132.44, 131.71, 129.75, 129.60, 127.99,
127.86, 123.65.
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.09.
Crystallographic data：Anorthic system, space group P-1, a=1.3060 (3) nm, b=1.4029 (3) nm, c=
1.4469 (3) nm, α=96.280 (3) °, β=106.826 (3) °, γ=94.816 (3) °, Z=2, V=2.5037 (10)
nm3, 1.550 Mg m of Dc=-3, m (MoK α)=1.063 mm-1, F (000)=1168.
Embodiment 4：
The preparation of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound：
3.440g (10.0mmol) diphenyl stannum dichloride, 1.864g is added in the 500mL there-necked flask for having nitrogen protection
(10.3mmol) p-nitrobenzoylhydrazide, 1.650g (11.0mmol) benzoyl formic acid and 95% methanol of 210mL solvent, in temperature
For reacting 22 h under conditions of 45 ~ 65 DEG C, cooling, filter, control solvent volatilization crystallization under conditions of 20 ~ 35 DEG C, obtain yellow
Transparent crystal, as 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound.Yield：84.3%.Fusing point：
276~278℃(dec).
Elementary analysiss (C108H76N12O20Sn4)：Value of calculation：C 55.51, H 3.28, N 7.19；Measured value：C 55.55, H
3.27, N 7.18.
FT-IR (KBr, ν/cm-1): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600,
1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 852,
817, 734, 719, 690, 590, 547, 451, 410.
1H NMR (500 MHz, CDCl3, δ/ppm): 8.44 (d,J= 8.8 Hz, 2H), 8.34 (d,J=
8.8 Hz, 2H), 8.15-8.18 (m, 2H), 7.86-7.88 (m, 4H), 7.50-7.59 (m, 9H).
13C NMR (126 MHz, CDCl3, δ/ppm): 173.24, 162.53, 152.49, 150.28,
137.91, 136.11, 135.35, 132.47, 132.44, 131.71, 129.75, 129.60, 127.99,
127.86, 123.65.
119Sn NMR (187 MHz, CDCl3, δ/ppm): -294.09.
Crystallographic data：Anorthic system, space group P-1, a=1.3060 (3) nm, b=1.4029 (3) nm, c=
1.4469 (3) nm, α=96.280 (3) °, β=106.826 (3) °, γ=94.816 (3) °, Z=2, V=2.5037 (10)
nm3, 1.550 Mg m of Dc=-3, m (MoK α)=1.063 mm-1, F (000)=1168.
Test example：
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide the coordination compound of the present invention, its Anticancer Activity in vitro is determined
Realized by MTT experiment method.
MTT analytic process：
With metabolism reduction 3- (4,5-Dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide it is
Basis.Succinate dehydrogenase in living cells mitochondria can make exogenous MTT be reduced to water-insoluble bluish violet crystallization first a ceremonial jade-ladle, used in libation
(Formazan) and it is deposited in cell, and dead cell no this function.Dimethyl sulfoxide (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell,
The optical density of characteristic wavelength is determined with microplate reader, can reflect indirectly living cells quantity.
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone the stannous phenide for being determined the preparation of embodiment 1 using mtt assay is joined
Inhibitory activity of the compound to human lung carcinoma cell (H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7).
Cell strain and cultivating system：H460, HepG2 and MCF7 cell strain takes from American. tissue incubator (ATCC).With containing
RPMI 1640 (GIBICO company) culture medium of 10% hyclone, in 5% (volume fraction) CO2, 37 DEG C of saturated humidity incubators
In vitro culture is inside carried out.
Test process：Test medicinal liquid (1nM ~ 10 μM) is added separately in each hole according to the Concentraton gradient of concentration, per
Individual concentration sets 6 parallel holes.Experiment is divided into drug study group (being separately added into the test medicine of variable concentrations), matched group and (only adds training
Nutrient solution and cell, are not added with testing medicine) and blank group (only adding culture medicine, be not added with cell and test medicine).Orifice plate after dosing is put
In 37 DEG C, 5%CO272h is cultivated in incubator.The activity of control drug is determined according to the method for test sample.Cultivating 72h
In orifice plate afterwards, add 40 μ L of MTT (4mg/mL being made into D-Hanks buffer) per hole.After 4h being placed at 37 DEG C, upper strata is removed
Clear liquid.Add 150 μ L DMSO per hole, 5min is vibrated, make Formazan crystallize dissolving.Finally, using automatic microplate reader in 570nm
The optical density in each hole is detected at wavelength.
Data processing：Data processing uses 7.0 program of Graph Pad Prism version, coordination compound IC50By journey
Nonlinear regression model (NLRM) with S-shaped dose response in sequence is fitted obtaining.
Thin to human lung carcinoma cell (H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) with MTT analytic process
Born of the same parents' strain is analyzed, and determines its IC50Value, as a result as shown in table 1, conclusion is：From data in table, with the 2- carbonyl of the present invention
Base -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound is used as cancer therapy drug, to human lung carcinoma cell (H460), people liver
Cancerous cell (HepG2) and human breast cancer cell (MCF7), can be used as the candidate compounds of cancer therapy drug with certain drug effect.
1 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound cancer therapy drug external activity test of table
Data.
| Human lung cancer | Human liver cancer | Human breast carcinoma | |
| Cell strain | H460 | HepG2 | MCF7 |
| IC50(μM) | 1.91±0.12 | 1.13±0.39 | 1.34±0.38 |
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound prepared by remaining embodiment is with mtt assay
Same to the active anticancer method of testing of human lung carcinoma cell (H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7)
Test example, test result is essentially identical with table 1.
The preferred embodiments of the present invention and test example is these are only, is not limited to the present invention, it is clear that the skill of this area
Art personnel can carry out various changes, modification without departing from the spirit and scope of the present invention to the present invention.If to the present invention's
These modifications and modification belong within the scope of the claims in the present invention and its equivalent technologies, belong to the protection model of the present invention
Enclose.
Claims (9)
1. a kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound, is the cooperation of following structure formula (I)
Thing：
(I)
Wherein Ph is phenyl.
2. coordinate containing a kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide as claimed in claim 1
Thing, its ir data：FT-IR (KBr, ν/cm-1): 3105, 3070, 3053, 3020, 2991, 1695,
1616, 1600, 1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012,
869, 852, 817, 734, 719, 690, 590, 547, 451, 410；Its nuclear-magnetism modal data：1H NMR (500
MHz, CDCl3, δ/ppm): 8.44 (d,J= 8.8 Hz, 2H), 8.34 (d,J= 8.8 Hz, 2H), 8.15-
8.18 (m, 2H), 7.86-7.88 (m, 4H), 7.50-7.59 (m, 9H)；13C NMR (126 MHz, CDCl3, δ/
ppm): 173.24, 162.53, 152.49, 150.28, 137.91, 136.11, 135.35, 132.47, 132.44,
131.71, 129.75, 129.60, 127.99, 127.86, 123.65；119Sn NMR (187 MHz, CDCl3, δ/
ppm): -294.09.
3. 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound as claimed in claim 1, wherein, institute
2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide the coordination compound that states is crystal structure, and its crystallographic data is as follows：
Anorthic system, space group P-1, a=1.3060 (3) nm, b=1.4029 (3) nm, c=1.4469 (3) nm, α=
96.280 (3) °, β=106.826 (3) °, γ=94.816 (3) °, 2.5037 (10) nm of Z=2, V=3, Dc=1.550
Mg·m-3, m (MoK α)=1.063 mm-1, F (000)=1168；In molecule, tin atom is hexa-coordinate distorted octahedron configuration.
4. described in claim 1,2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound has certain heat
Stability range, can stable existence below 276 DEG C.
5. the preparation side of the 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound described in claim 1
Method, is characterized in that adding diphenyl stannum dichloride, p-nitrobenzoylhydrazide, benzoyl first in the reaction vessel for having nitrogen protection
Acid and 95% methanol of solvent, react 5 ~ 24 h under conditions of temperature is 45 ~ 65 DEG C, cool down, filter, under conditions of 20 ~ 35 DEG C
Control solvent volatilization crystallization, obtains yellow transparent crystal, and as 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide is joined
Compound.
6. the method for preparation as claimed in claim 5, it is characterised in that the diphenyl stannum dichloride, p-nitrophenyl formyl
Hydrazine, the amount ratio of the material of benzoyl formic acid three are 1:(1~1.05):(1.05~1.15).
7. the method for preparation as claimed in claim 5, it is characterised in that 95% methanol usage of the solvent is per mM two
Phenyl dichloro stannum adds 15 ~ and 35 milliliters.
8. described in claim 1,2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone stannous phenide coordination compound is preparing anticarcinogen
Application in thing.
9. the application described in claim 8, the wherein cancerous cell are human lung carcinoma cell, human liver cancer cell, human breast cancer cell.
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