CN104277076A - Compound for enhancing anti-infection capacity of plants, and preparation method and application thereof - Google Patents
Compound for enhancing anti-infection capacity of plants, and preparation method and application thereof Download PDFInfo
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- CN104277076A CN104277076A CN201410513757.0A CN201410513757A CN104277076A CN 104277076 A CN104277076 A CN 104277076A CN 201410513757 A CN201410513757 A CN 201410513757A CN 104277076 A CN104277076 A CN 104277076A
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- planting body
- thiosemicarbazide
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 230000002924 anti-infective effect Effects 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 230000002708 enhancing effect Effects 0.000 title abstract 3
- 239000003814 drug Substances 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims description 21
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 14
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 14
- 238000001556 precipitation Methods 0.000 claims description 14
- 229910052707 ruthenium Inorganic materials 0.000 claims description 13
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 239000012467 final product Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 9
- 208000015181 infectious disease Diseases 0.000 abstract description 5
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 244000063299 Bacillus subtilis Species 0.000 abstract description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 abstract description 3
- 241000222122 Candida albicans Species 0.000 abstract description 3
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 3
- 229940095731 candida albicans Drugs 0.000 abstract description 3
- 210000000963 osteoblast Anatomy 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 241000588724 Escherichia coli Species 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 231100000956 nontoxicity Toxicity 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 11
- OXACXUIQRLDCKR-UHFFFAOYSA-N CC1=CC=C(C=C1)C(C)C.C1(=CC=CC=C1)NC(NN)=S Chemical compound CC1=CC=C(C=C1)C(C)C.C1(=CC=CC=C1)NC(NN)=S OXACXUIQRLDCKR-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- -1 aryl ruthenium Chemical compound 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 5
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000002223 garnet Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 0 **C(*NC=Cc(cc1)ccc1F)=S Chemical compound **C(*NC=Cc(cc1)ccc1F)=S 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 230000004069 differentiation Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003402 anti-promotion Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000004513 dentition Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000004072 osteoblast differentiation Effects 0.000 description 1
- 230000001582 osteoblastic effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a compound for enhancing anti-infection capacity of plants disclosed as structural formula (I), and a preparation method and application thereof. The chemical name is monochlorinated-chloro-p-fluoridated-phenyl-2-N<4>-phenylthiosemicarbazidomonomethylisopropylbenzo ruthenium (II). The compound has strong bactericidal activity for Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 25922), Candida albicans (ATCC 10231) and Bacillus subtilis black variant (ATCC 9372), has the advantages of excellent mold resistance and no toxicity, has the function of promoting growth of osteoblasts, is used for preparing drugs for enhancing plant performance and preventing plant related infections, and has obvious application potential. The preparation method is simple, and has the advantages of accessible raw materials and low cost.
Description
Technical field
The present invention relates to field of compound preparation, be specifically related to a kind of for aryl ruthenium complexe improving planting body anti-infection ability and its production and use.
Background technology
The planting materials such as tooth implant and bone planting body have become the important restorative procedure of defect of dentition and bone loss, but infection rate of such operation is very high, may cause a large amount of antibiotic therapy, remove the serious consequences such as planting body is even dead.Planting body infections relating major cause occurred frequently has 2 points: bacterial plaque implant surface assemble and Osseointegrated implants interface resistivity low.In order to avoid planting body infections relating, graft should have the premium properties of two aspects: excellent anti-microbial property and promotion Oesteoblast growth function.Therefore, finding the compound with above two kinds of performances is necessary for improving planting body performance with prevention planting body infections relating.
Summary of the invention
The object of the invention is to the research according to existing aryl ruthenium complexe, a kind of aryl ruthenium complexe and its production and use is provided.
Technical scheme provided by the invention is:
For improving a compound for planting body anti-infection ability, its structural formula is formula (I):
Wherein in an embodiment, compound of the present invention is such as aryl ruthenium complexe, and its chemical name is that monochlor(in)ate one chlorine fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes ruthenium (II);
Its structural formula is:
Its physico-chemical property is: garnet crystal, soluble in water and organic solvent, and its hydrogen nuclear magnetic resonance modal data is
1h NMR (CDCl
3solvent): δ: 8.903 (1H, s, CH=N), (8.429-8.382 2H, m, phenyl-H), (7.505-7.424 7H, m, phenyl-H), 5.765 (1H, d, J=6.0Hz, p-cym phenyl-H), 5.202 (1H, d, J=5.9Hz, p-cym phenyl-H), 5.092 (1H, d, J=6.0Hz, p-cym phenyl-H), 5.046 (1H, d, J=6.0Hz, p-cym phenyl-H), 2.713-2.621 (1H, m, p-cym CH (CH
3)
2), 2.117 (3H, s, p-cym CCH
3), 1.224 (3H, d, J=6.9Hz, p-cym CH (CH
3)
2), 1.165 (3H, d, J=6.9Hz, p-cym CH (CH
3)
2) ppm..
Another object of the present invention is to provide described for improving the preparation method of the compound of planting body anti-infection ability, and the described compound for improving planting body anti-infection ability is prepared by the following method:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of 65-70 weight part and 470-480 weight part is dissolved in the dehydrated alcohol of 1450-1500 weight part, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 27-35 weight part
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 22-26 weight part is dissolved in the dehydrated alcohol of 870-910 weight part jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 4.5-5.5 weight part is closed for dichloride-two-cymene of thiosemicarbazide and 4-6 weight part the methylene dichloride that two rutheniums (II) are dissolved in 1230-1250 weight part, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
Preferably, the described compound for improving planting body anti-infection ability, hydrate ruthenium trichloride described in described step one to be ruthenium weight content be 37% hydrate ruthenium trichloride; The purity of described γ-terpinene is 95%.
Preferably, the described compound for improving planting body anti-infection ability, prepare by the following method:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of 69 weight parts and 478 weight parts is dissolved in the dehydrated alcohol of 1480 weight parts, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 31 weight parts
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 23 weight parts is dissolved in the dehydrated alcohol of 888 weight parts jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 5.1 weight parts is closed for dichloride-two-cymene of thiosemicarbazide and 6 weight parts the methylene dichloride that two rutheniums (II) are dissolved in 1244 weight parts, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
Another object of the present invention is to provide a kind of described for improving the purposes of the compound of planting body anti-infection ability, and it is for the preparation of the medicine improving planting body anti-infection ability.
Compared with the prior art, the beneficial effect that the present invention has is:
First, add phenylamino in the compound for improving planting body anti-infection ability of the present invention and to fluorophenyl, phenyl ring and the carbon-to-nitrogen double bon be connected form conjugation, and molecule is more stable, thus improves its aromaticity, and its activity is higher;
Secondly, compound for improving planting body anti-infection ability of the present invention all has very strong bactericidal properties to streptococcus aureus (ATCC 6538), colon bacillus (ATCC 25922), Candida albicans (ATCC 10231), Bacillus subtilis endophyticus (ATCC 9372), there is excellent anti-microbial property, and scleroblast is shown to the effect of growth promoting effects, nontoxic, there is application potential clearly.
Finally, the preparation method of the compound for improving planting body anti-infection ability of the present invention is simple, and raw material is easy to get, and has the advantage that cost is low.
Accompanying drawing explanation
Fig. 1 for described in one of them embodiment of the present invention for improving the nmr spectrum of the compound of planting body anti-infection ability.
Fig. 2 for described in one of them embodiment of the present invention for improving the absorbancy figure of the compound of planting body anti-infection ability.
Fig. 3 for described in one of them embodiment of the present invention for improving the alkaline phosphatase activities figure of the compound of planting body anti-infection ability.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, can implement according to this with reference to specification sheets word to make those skilled in the art.
Embodiment 1:
Compound for improving planting body anti-infection ability of the present invention is aryl ruthenium complexe, and its chemical name is that monochlor(in)ate one chlorine fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes ruthenium (II);
Its structural formula is:
Its physico-chemical property is: garnet crystal, soluble in water and organic solvent.
Monochlor(in)ate one chlorine of the present invention fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes the preparation method of ruthenium (II), and its concrete steps are as follows:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of the ruthenium weight content 37% of 65 weight parts and the purity 95% of 470 weight parts is dissolved in the dehydrated alcohol of 1450 weight parts, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 27 weight parts
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 22 weight parts is dissolved in the dehydrated alcohol of 870 weight parts jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 4.5 weight parts is closed for dichloride-two-cymene of thiosemicarbazide and 4 weight parts the methylene dichloride that two rutheniums (II) are dissolved in 1230 weight parts, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
Embodiment 2:
Compound for improving planting body anti-infection ability of the present invention is aryl ruthenium complexe, and its chemical name is that monochlor(in)ate one chlorine fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes ruthenium (II);
Its structural formula is:
Its physico-chemical property is: garnet crystal, soluble in water and organic solvent.
Monochlor(in)ate one chlorine of the present invention fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes the preparation method of ruthenium (II), and its concrete steps are as follows:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of the ruthenium weight content 37% of 70 weight parts and the purity 95% of 480 weight parts is dissolved in the dehydrated alcohol of 1500 weight parts, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 35 weight parts
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 26 weight parts is dissolved in the dehydrated alcohol of 910 weight parts jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 5.5 weight parts is closed for dichloride-two-cymene of thiosemicarbazide and 6 weight parts the methylene dichloride that two rutheniums (II) are dissolved in 1250 weight parts, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
Embodiment 3:
Compound for improving planting body anti-infection ability of the present invention is aryl ruthenium complexe, and its chemical name is that monochlor(in)ate one chlorine fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes ruthenium (II);
Its structural formula is:
Its physico-chemical property is: garnet crystal, soluble in water and organic solvent.
Monochlor(in)ate one chlorine of the present invention fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes the preparation method of ruthenium (II), and its concrete steps are as follows:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of the ruthenium weight content 37% of 69 weight parts and the purity 95% of 478 weight parts is dissolved in the dehydrated alcohol of 1480 weight parts, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 31 weight parts
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 23 weight parts is dissolved in the dehydrated alcohol of 888 weight parts jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 5.1 weight parts is closed for dichloride-two-cymene of thiosemicarbazide and 6 weight parts the methylene dichloride that two rutheniums (II) are dissolved in 1244 weight parts, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
As shown in Figure 1, its hydrogen nuclear magnetic resonance modal data is
1hNMR (CDCl
3solvent): δ: 8.903 (1H, s, CH=N), (8.429-8.382 2H, m, phenyl-H), (7.505-7.424 7H, m, phenyl-H), 5.765 (1H, d, J=6.0Hz, p-cym phenyl-H), 5.202 (1H, d, J=5.9Hz, p-cym phenyl-H), 5.092 (1H, d, J=6.0Hz, p-cym phenyl-H), 5.046 (1H, d, J=6.0Hz, p-cym phenyl-H), 2.713-2.621 (1H, m, p-cym CH (CH
3)
2), 2.117 (3H, s, p-cym CCH
3), 1.224 (3H, d, J=6.9Hz, p-cym CH (CH
3)
2), 1.165 (3H, d, J=6.9Hz, p-cym CH (CH
3)
2) ppm..
Its pharmaceutical activity and application thereof is further illustrated below by pharmacodynamic experiment.
Experiment one: antibacterial ability is tested:
In sterilizing test tubes, add 1mL concentration is 10
6the bacterium liquid of/ml, adds the Organic metal ruthenium ion pair compound that 1mg embodiment 3 obtains, and cultivates 24h for 37 DEG C.Cultivate after time point, substratum collects with doubling dilution, and extension rate is 10 times and spread plate method detection viable count.Test-results shows: the product obtained by the present invention all has very strong bactericidal properties to streptococcus aureus (ATCC 6538), colon bacillus (ATCC 25922), Candida albicans (ATCC 10231), Bacillus subtilis endophyticus (ATCC 9372), and its sterilizing rate reaches more than 99.999%.
Experiment two: activity of osteoblast proliferation is tested:
Aryl ruthenium complexe 1mg embodiment 3 obtained is placed in 24 orifice plates, and 1ml density is 2 × 10
4the mouse bone-forming cell suspension inoculation of/ml, in 24 orifice plates, then cultivates 1,4 and 7 day.After predetermined point of time, every hole adds the MTT (5mg/ml) of 200 μ l and 800 μ l serum-frees without phenol red DMEM.37 DEG C hatch 4 hours after inhale abandon supernatant, add 1ml dimethyl sulfoxide (DMSO) (DMSO) dissolve generate crystallisate, every hole is got three part of 200 μ l lysate and is forwarded 96 well culture plates to, with spectrophotometer in 490nm place survey its OD value.Result shows, as shown in Figure 2, monochlor(in)ate one chlorine of the present invention fluoridizes benzene-2-contracting N for a pair
4-phenyl thiosemicarbazide monomethyl isopropyl benzene closes ruthenium (II) and shows obvious cell-proliferation activity.
Experiment three: initial cell differentiation capability is analyzed:
Active by the alkaline phosphatase (ALP) compared as the product of the present invention of scleroblast initial differentiation marker thing, check the impact that product of the present invention breaks up mouse bone-forming cell.In order to more osteoblastic differentiation capability, be 2 × 10 by 1ml density
4the mouse bone-forming cell of/ml is inoculated in 24 orifice plates, and cultivates 1 day.Subsequently, respectively with not containing the substratum of product of the present invention and the division culture medium process cell containing 1mg product of the present invention, and 5%CO is being contained
237 DEG C of thermostat containers in cultivate, to measure ALP active the 7th day and the 14th day after incubation.Experiment finds, as shown in Figure 3, product of the present invention is high by 46% at the ALP specific activity substratum of display in the 14th day, and this shows that osteoblast differentiation ability is obviously improved.
Experiment four: cytotoxicity analysis:
The cytotoxicity size of product of the present invention is assessed using the activity of serum lactic dehydrogenase (LDH) as cytotoxicity index.Be 1 × 10 by concentration
4the mouse bone-forming cell of individual cell is inoculated in 24 orifice plates, and cultivates 1 day.Subsequently, respectively with not containing the substratum of product of the present invention and the division culture medium process cell containing 1mg product of the present invention, and CO is being contained
237 DEG C of thermostat containers in cultivate 24 hours, get supernatant liquor after centrifugal and detect for LDH activity.Experimental result is as shown in the table.
| ? | Substratum | Product of the present invention |
| LDH activity | 308 | 293 |
Can be shown by upper table, the compound for improving planting body anti-infection ability of the present invention shows through cell toxicity test, and the LDH activity containing product free medium of the present invention is 293, a little less than the substratum 308 not containing product of the present invention, illustrates that product of the present invention is nontoxic.
Although embodiment of the present invention are open as above, but it is not restricted to listed in specification sheets and embodiment utilization, it can be applied to various applicable the field of the invention completely, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the universal that claim and equivalency range limit, the present invention is not limited to specific details and illustrates here and the embodiment described.
Claims (5)
1. for improving a compound for planting body anti-infection ability, it is characterized in that, its structural formula is formula (I):
2. the compound for improving planting body anti-infection ability according to claim 1, is characterized in that, the described compound for improving planting body anti-infection ability is prepared by the following method:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of 65-70 weight part and 470-480 weight part is dissolved in the dehydrated alcohol of 1450-1500 weight part, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 27-35 weight part
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 22-26 weight part is dissolved in the dehydrated alcohol of 870-910 weight part jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 4.5-5.5 weight part is closed for dichloride-two-cymene of thiosemicarbazide and 4-6 weight part the methylene dichloride that two rutheniums (II) are dissolved in 1230-1250 weight part, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
3. the compound for improving planting body anti-infection ability according to claim 2, is characterized in that, hydrate ruthenium trichloride described in described step one is the hydrate ruthenium trichloride of ruthenium weight content 37%; The purity of described γ-terpinene is 95%.
4. the compound for improving planting body anti-infection ability according to claim 3, is characterized in that, the described compound for improving planting body anti-infection ability is prepared by the following method:
Step one, the γ-terpinene of the hydrate ruthenium trichloride of 69 weight parts and 478 weight parts is dissolved in the dehydrated alcohol of 1480 weight parts, reflux stirs 6 hours, standing precipitation obtains the compound with formula (III), and namely dichloride-two-cymene closes two rutheniums (II);
Step 2, takes the N of 31 weight parts
4the p-Fluorobenzenecarboxaldehyde of-phenyl thiosemicarbazide and 23 weight parts is dissolved in the dehydrated alcohol of 888 weight parts jointly, is heated to 70 DEG C, after 4 hours, and standing precipitation obtains the compound with formula (IV), and namely p-Fluorobenzenecarboxaldehyde contracting benzene is for thiosemicarbazide;
Step 3, the p-Fluorobenzenecarboxaldehyde contracting benzene of 5.1 weight parts is closed for dichloride-two-cymene of thiosemicarbazide and 6 weight parts the methylene dichloride that two rutheniums (II) are dissolved in 1244 weight parts, room temperature 22-25 DEG C is stirred 3 hours, separates out dark red solid, to obtain final product.
5. as claimed in claim 1 for improving a purposes for the compound of planting body anti-infection ability, it is characterized in that, for the preparation of the medicine improving planting body anti-infection ability.
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Cited By (6)
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| CN105239068A (en) * | 2015-11-17 | 2016-01-13 | 广西中医药大学 | Stainless steel material modified through ruthenium complex and preparation method and application thereof |
| CN105251054A (en) * | 2015-11-17 | 2016-01-20 | 广西中医药大学 | Method for preparing titanium dioxide nanotubes with antibacterial and anticancer functions through ruthenium complex |
| CN105288745A (en) * | 2015-11-17 | 2016-02-03 | 广西中医药大学 | Antibacterial and anti-cancer titanium dioxide nano-tube preparation method |
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| CN105412982A (en) * | 2015-11-17 | 2016-03-23 | 广西中医药大学 | Method for improving antibacterial and anticancer effects of titanium dioxide nanotubes |
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| CN105239068A (en) * | 2015-11-17 | 2016-01-13 | 广西中医药大学 | Stainless steel material modified through ruthenium complex and preparation method and application thereof |
| CN105251054A (en) * | 2015-11-17 | 2016-01-20 | 广西中医药大学 | Method for preparing titanium dioxide nanotubes with antibacterial and anticancer functions through ruthenium complex |
| CN105288745A (en) * | 2015-11-17 | 2016-02-03 | 广西中医药大学 | Antibacterial and anti-cancer titanium dioxide nano-tube preparation method |
| CN105288726A (en) * | 2015-11-17 | 2016-02-03 | 广西中医药大学 | Ruthenium coordination compound modified titanium metal material, preparation method and uses thereof |
| CN105412982A (en) * | 2015-11-17 | 2016-03-23 | 广西中医药大学 | Method for improving antibacterial and anticancer effects of titanium dioxide nanotubes |
| CN105239068B (en) * | 2015-11-17 | 2017-11-03 | 广西中医药大学 | Stainless steel material of ruthenium complex modification and preparation method thereof and purposes |
| CN105251054B (en) * | 2015-11-17 | 2018-06-22 | 广西中医药大学 | The method that the titania nanotube with antibacterial anticancer is prepared using ruthenium complex |
| CN105288726B (en) * | 2015-11-17 | 2018-06-22 | 广西中医药大学 | Titanium metal material of ruthenium complex modification and its preparation method and application |
| CN105457088A (en) * | 2015-11-20 | 2016-04-06 | 广西中医药大学 | Method for preparing titanium metal with antimicrobial and anticancer performance |
| CN105457088B (en) * | 2015-11-20 | 2018-04-03 | 广西中医药大学 | A kind of method for preparing the titanium with antibacterial anti-cancer properties |
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