CN105061475A - Polynitrogen schiff base copper complex and preparation method and application thereof - Google Patents
Polynitrogen schiff base copper complex and preparation method and application thereof Download PDFInfo
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- 239000002262 Schiff base Substances 0.000 title claims abstract description 34
- -1 schiff base copper complex Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 7
- 239000002601 urease inhibitor Substances 0.000 claims abstract description 7
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 claims description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- 229960003280 cupric chloride Drugs 0.000 claims description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229940090496 Urease inhibitor Drugs 0.000 claims description 6
- 150000004699 copper complex Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 108010046334 Urease Proteins 0.000 abstract description 6
- 239000013641 positive control Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 206010019375 Helicobacter infections Diseases 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 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
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
- 229960001171 acetohydroxamic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 208000023652 chronic gastritis Diseases 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 208000017215 gastric mucosa-associated lymphoid tissue lymphoma Diseases 0.000 description 1
- 208000018685 gastrointestinal system disease Diseases 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000036269 ulceration Effects 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention relates to a polynitrogen schiff base copper complex and a preparation method and an application thereof, and belongs to the polynitrogen schiff base complex technical field. The polynitrogen schiff base copper complex is a mononuclear compound and has a structural formula shown in the description, wherein R is defined in the description. The polynitrogen schiff base copper complex has the characteristics of simple synthesis, convenient purification, higher yield, and good stability in air; the preparation steps are simple and feasible; the polynitrogen schiff base copper complex is mainly applied in preparation of urease inhibitors, has quite strong urease inhibitory activity, and has the inhibition ability superior to that of a positive control drug.
Description
Technical field
The present invention relates to a kind of many nitrogen schiff bases copper complex and its preparation method and application, belong to the presence of Schiff-base complex technical field of copper.
Background technology
Schiff bases is the organic compound that a class contains C=N group, carries out condensation reaction obtain by carbonyl compound and various dissimilar amine or hydrazine class compound in alcoholic solution.Can obtain from monodentate to multiple tooth by changing the substituting group of linking group, asymmetric from being symmetric to, the Shiff base derivative of each spline structure such as from chain to ring-type.Schiff bases has stronger coordination ability, can form stable title complex with most metal ion in periodictable.Many nitrogen presence of Schiff-base complex is widely used in functional materials, the fields such as medicine, Dong, Y.B.; Zhao, X.; Huang, R.Q.Inorg.Chem.2004,43,5603-5612; Alghoo, S.; Slebodnick, C.Polyhedron2014,67,11-18; Lee, S.M.; Ali, H.M.; Sim, H.M.; Malek, S.N.A.; Lo, K.K.Inorg.Chim.Acta2013,406,272-278. discloses the application of many nitrogen presence of Schiff-base complex at functional materials and pharmaceutical field.
Hp is a kind of gram negative bacterium, is the main pathogenic of chronic gastritis, peptide ulceration, gastric mucosa-associated lymphoid tissue lymphoma and cancer of the stomach.Hp can only in very narrow pH scope: survive in about 6 ~ 8, pH lower than 4 time will be killed rapidly.And why it can survive in stomach, having benefited from it has high reactivity urase.Urea seeding can be hydrolyzed to ammonia and carbonic acid gas by urase, and the ammonia cloud protective layer of formation can make Hp survive under gastric acid environment.Therefore, want to eliminate the helicobacter pylori infection that is difficult to effect a radical cure thus treat the gastrointestinal system disease that caused by it, just must suppress the activity of urase, to reach destruction ammonia cloud protective layer and then to kill the object of Hp.
Common urease inhibitor can be divided into organic molecule and the large class of metal ion two.It is short mostly to there is effective suppression time in fluorescence probe class inhibitor, and efficiency is low, easily runs off, and has the shortcomings such as general resistance.Although heavy metal ion class inhibitor inhibition is better, because its toxicity is comparatively large, the biological activity of other enzymes can be affected, make it apply and receive certain restriction.Therefore, the urease inhibitor finding high-efficiency low-toxicity is significant.The title complex selecting structure to have diversity and a Modulatory character can integrate the synergistic effect between Medicine small molecule and metal ion as urease inhibitor, makes up organic molecule and metal ion separately as shortcoming during inhibitor.Qin, J.; Lei, N.; Zhu, H.L.J.Coord.Chem.2014,67,1279-1289; Xu, Y.P.; Chen, Y.H.; Chen, Z.J.; Qin, J.; Qian, S.S.; Zhu, H.L.Eur.J.Inorg.Chem.2015,2076-2084. disclose nitrogen heterocyclic title complex suppresses field application at urase.
Summary of the invention
The object of this invention is to provide a kind of many nitrogen schiff bases copper complex, have synthesis simple, be convenient to purify, productive rate is higher, the feature that property stable in the air is good; The present invention provides its preparation method and application simultaneously.
Many nitrogen schiff bases copper complex of the present invention, its structural formula is as follows:
Wherein: R is
The preparation method of many nitrogen schiff bases copper complex of the present invention, comprises the following steps:
(1) vazadrine or 3-pyridine acethydrazide are mixed with 2-ethanoyl pyrazine, formic acid, add ethanol and carry out back flow reaction, after reaction terminates, be cooled to room temperature, filter, obtain nitrogen heterocyclic schiff bases solid-vazadrine contracting acetylpyrazine or the 3-pyridine acethydrazide contracting acetylpyrazine of white;
(2) be dissolved in methylene dichloride by vazadrine contracting acetylpyrazine or 3-pyridine acethydrazide contracting acetylpyrazine, cupric chloride is dissolved in methyl alcohol, leaves standstill, obtain many nitrogen schiff bases copper complex by after above-mentioned two kinds of solution mixing.
Wherein:
The usage ratio of vazadrine or 3-pyridine acethydrazide, 2-ethanoyl pyrazine, formic acid, ethanol is 1:1:0.08:5 in step (1), and wherein, vazadrine, 3-pyridine acethydrazide, 2-ethanoyl pyrazine are in mmole number, and formic acid and ethanol are in milliliter.
In step (1), return time is 4-6 hour.
The usage ratio of vazadrine contracting acetylpyrazine or 3-pyridine acethydrazide contracting acetylpyrazine, cupric chloride, methylene dichloride, methyl alcohol is 1:2:125:125 in step (2), wherein, vazadrine contracting acetylpyrazine, 3-pyridine acethydrazide contracting acetylpyrazine, cupric chloride are in mmole number, and methylene dichloride and methyl alcohol are in milliliter.
In step (2), time of repose is 10-12 days.
Reaction equation of the present invention is as follows:
R
1for
time, R is
r
1for
time, R is
Many nitrogen Schiff copper complex of the present invention is used for the preparation of urease inhibitor.
The present invention infrared, ultimate analysis (C, H, N), X-ray single crystal diffraction characterize and confirm the structure of many nitrogen schiff bases copper complex.
Many nitrogen schiff bases copper complex of the present invention has very strong urease inhibiting activity, and half-inhibition concentration is respectively 5.21 μm of ol/L, 2.02 μm of ol/L.
Beneficial effect of the present invention is as follows:
Many nitrogen schiff bases copper complex synthesis of the present invention is simple, and be convenient to purify, productive rate is higher, and property stable in the air is good; Its preparation method is simple; Many nitrogen schiff bases copper complex of the present invention is mainly used in the preparation of urease inhibitor, has very strong urease inhibiting activity, and rejection ability is better than positive control medicine.
Accompanying drawing explanation
Fig. 1 is the single crystal structure figure of the embodiment of the present invention 1;
Fig. 2 is the single crystal structure figure of the embodiment of the present invention 2.
Embodiment
Below in conjunction with embodiment, the present invention is described further.
Detecting instrument in embodiment is: Perkin-Elmer240C type elemental analyser, Vector22Bruker spectrophotometer (400-4000cm
-1), BrukerSmartApexCCD single crystal diffractometer and BioRad550 type microplate reader etc.
Embodiment 1
The preparation method that contracting acetylpyrazine in vazadrine closes cupric chloride is as follows:
(1) by vazadrine (1.64g, 12mmol), 2-ethanoyl pyrazine (1.46g, 12mmol), the formic acid of 1.0mL is dissolved in 60mL ethanol, back flow reaction 4h, be cooled to room temperature, the sedimentation and filtration of generation, cold washing with alcohol, obtain white solid vazadrine contracting acetylpyrazine 2.75g, productive rate: 95%; Compound is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3483,3183,1671,1549,1458,1380,1302,1221,1170,1124,1107,840,802,753,723,685,628,583,480.
Results of elemental analyses: calculated value (%): C, 59.74; H, 4.59; N, 29.03; Measured value (%): C, 59.84; H, 4.56; N, 29.19%.
(2) by cupric chloride (13.6mg, 0.08mmol) be dissolved in 5mL methanol solution, then it is slowly instilled containing vazadrine contracting acetylpyrazine (9.6mg, in 5mL dichloromethane solution 0.04mmol), leave standstill 10 days, occur the blackish green crystal of 10.1mg, filter, and by methanol wash three times, be placed in Calcium Chloride Powder Anhydrous moisture eliminator inner drying and obtain product, productive rate 67%.Product is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3443,3054,2618,2361,1631,1529,1498,1448,1367,1323,1297,1236,1148,1068,1037,849,755,712,686,518,459,418.
Results of elemental analyses: calculated value (%): C, 38.36; H, 2.95; N, 18.64; Measured value (%): C, 38.51; H, 2.90; N, 18.69.
The structural formula that contracting acetylpyrazine in vazadrine closes cupric chloride is as follows:
The character such as above-mentioned complex molecule formula, proterties, productive rate are in table 1.
Embodiment 2
The preparation method that 3-pyridine acethydrazide contracting acetylpyrazine closes cupric chloride is as follows:
(1) by 3-pyridine acethydrazide (3.96g, 12mmol), 2-ethanoyl pyrazine (1.46g, 12mmol), the formic acid of 1.0 milliliters is dissolved in 60mL ethanol, back flow reaction 6 hours, be cooled to room temperature, the sedimentation and filtration of generation, cold washing with alcohol, obtain white solid 3-pyridine acethydrazide contracting acetylpyrazine 2.30g, productive rate: 75%; Compound is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3358,3053,2897,1957,1686,1614,1586,1516,1475,1427,1375,1322,1294,1256,1170,1109,1047,1015,962,916,854,799,756,723,682,608,501,471.
Results of elemental analyses: calculated value (%): C, 61.16; H, 5.13; N, 27.43; Measured value (%): C, 61.34; H, 5.11; N, 29.54%.
(2) by cupric chloride (13.6mg, 0.08mmol) be dissolved in 5mL methanol solution, then it is slowly instilled containing 3-pyridine acethydrazide contracting acetylpyrazine (10.2mg, in 5mL dichloromethane solution 0.04mmol), leave standstill 12 days, occur the blackish green crystal of 9.0mg, filter, and by methanol wash three times, be placed in Calcium Chloride Powder Anhydrous moisture eliminator inner drying and obtain product, productive rate 58%.Product is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3440,3158,3053,2921,2866,2749,2068,1961,1843,1609,1545,1495,1454,1415,1380,1296,1253,1186,1141,1076,1036,929,861,809,736,684,642,494,460,418.
Results of elemental analyses: calculated value (%): C, 40.06; H, 3.36; N, 17.97; Measured value (%): C, 40.18; H, 3.34; N, 18.06.
The structural formula that 3-pyridine acethydrazide contracting acetylpyrazine closes cupric chloride is as follows:
The character such as above-mentioned complex molecule formula, proterties, productive rate are in table 1.
Table 1 nitrogen schiff bases more than two kinds copper complex
| Sequence number | Complex molecule formula | Proterties | Productive rate (%) |
| Embodiment 1 | (C 12H 11N 5O)CuCl 2 | Blackish green crystal | 67 |
| Embodiment 2 | (C 13H 13N 5O)CuCl 2 | Blackish green crystal | 58 |
Below the title complex that embodiment 1 ~ 2 obtains is detected.
1, the single crystal structure of many nitrogen schiff bases copper complex characterizes:
Testing tool is BrukerSmartApexCCD single crystal diffractometer, with Mo-K α (λ=0.071073nm) ray, tests 25 DEG C time by the scan pattern of ω/2 θ.Data are revised by SAINT, and Lorentz revises and the elimination of polarizing effect obtains.Absorbing to revise uses the SADABS of Bruker to supplement.Molecular structure has directly been solved with SHELXL-97.The position of atoms metal and around adjacent atoms is measured by the method for direct E-maps, and other non-hydrogen atoms are by Fourier transform, and its fine structure is progressively determined in least-squares refinement.Hydrogen atom is then finally determined at the position calculating gained, and has unified U
isovalue (accompanying drawing 1 ~ 2).Detected result is as shown in table 2.
The single crystal diffraction data sheet of table 2 embodiment 1 and embodiment 2
aR
1＝Σ||C|-|F
c||/ΣF
o|.
bwR
2＝[Σw(F
o 2-F
c 2)
2/Σw(F
o 2)]
1/2。
2, the effect of the present invention's many nitrogen schiff bases copper complex detects.
Testing method and step: the huge beans urase (10kU/L) of 25 μ L adds 25 μ L sample solution (different concns, DMSO/H
2o=1:1 dissolve) in 96 well culture plates 37 DEG C cultivate 1 hour, add 0.2mL100mMHEPES damping fluid (pH=6.8) (include: 500mM urea and 0.002% phenol red) again, with N-acetylhydroxylamine as positive control, calculate when pH of buffer rises to 7.7 by 6.8 the time used, and OD value is detected, calculation of half inhibitory concentration IC by microplate reader under 570nm wavelength
50.
Half-inhibition concentration is less, and show that the urease inhibiting activity of compound is better, the urease inhibiting activity test result of embodiment 1 ~ 2 and positive control is as table 3.
Table 3 urease inhibiting activity table with test results (μm ol/L)
| Numbering | IC 50 |
| Embodiment 1 | 5.21 |
| Embodiment 2 | 2.02 |
| Positive control | 6.28 |
Claims (7)
1. the schiff bases of nitrogen a more than copper complex, is characterized in that its structural formula is as follows:
Wherein: R is
2. a preparation method for many nitrogen schiff bases copper complex according to claim 1, is characterized in that comprising the following steps:
(1) vazadrine or 3-pyridine acethydrazide are mixed with 2-ethanoyl pyrazine, formic acid, add ethanol and carry out back flow reaction, after reaction terminates, be cooled to room temperature, filter, obtain nitrogen heterocyclic schiff bases solid-vazadrine contracting acetylpyrazine or the 3-pyridine acethydrazide contracting acetylpyrazine of white;
(2) be dissolved in methylene dichloride by vazadrine contracting acetylpyrazine or 3-pyridine acethydrazide contracting acetylpyrazine, cupric chloride is dissolved in methyl alcohol, leaves standstill, obtain many nitrogen schiff bases copper complex by after above-mentioned two kinds of solution mixing.
3. the preparation method of many nitrogen schiff bases copper complex according to claim 2; it is characterized in that: the usage ratio of vazadrine or 3-pyridine acethydrazide, 2-ethanoyl pyrazine, formic acid, ethanol is 1:1:0.08:5 in step (1); wherein; vazadrine, 3-pyridine acethydrazide, 2-ethanoyl pyrazine are in mmole number, and formic acid and ethanol are in milliliter.
4. the preparation method of many nitrogen schiff bases copper complex according to claim 2, is characterized in that: in step (1), return time is 4-6 hour.
5. the preparation method of many nitrogen schiff bases copper complex according to claim 2, it is characterized in that: the usage ratio of vazadrine contracting acetylpyrazine or 3-pyridine acethydrazide contracting acetylpyrazine, cupric chloride, methylene dichloride, methyl alcohol is 1:2:125:125 in step (2), wherein, vazadrine contracting acetylpyrazine, 3-pyridine acethydrazide contracting acetylpyrazine, cupric chloride are in mmole number, and methylene dichloride and methyl alcohol are in milliliter.
6. the preparation method of many nitrogen schiff bases copper complex according to claim 2, is characterized in that: in step (2), time of repose is 10-12 days.
7. an application for many nitrogen schiff bases copper complex according to claim 1, is characterized in that: for the preparation of urease inhibitor.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977505A (en) * | 2017-04-12 | 2017-07-25 | 山东理工大学 | Oxadiazole carboxylic acid metal's complex and its preparation method and application |
| CN108003178A (en) * | 2017-12-22 | 2018-05-08 | 辽宁师范大学 | Acylhydrazone copper (II) complex and preparation method thereof and its application in urease activity is suppressed |
| CN111234257A (en) * | 2020-03-13 | 2020-06-05 | 南昌航空大学 | Schiff base zinc complex functionalized polyion liquid and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911190A (en) * | 2012-10-26 | 2013-02-06 | 商丘师范学院 | Ethanol 2-hydroxyl naphthylaldehyde thiosemicarbazone o-phenanthroline polymerized metal complex and application thereof |
| CN104151331A (en) * | 2014-08-21 | 2014-11-19 | 山东理工大学 | Metal complex having urease inhibiting activity, and preparation method and application thereof |
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2015
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911190A (en) * | 2012-10-26 | 2013-02-06 | 商丘师范学院 | Ethanol 2-hydroxyl naphthylaldehyde thiosemicarbazone o-phenanthroline polymerized metal complex and application thereof |
| CN104151331A (en) * | 2014-08-21 | 2014-11-19 | 山东理工大学 | Metal complex having urease inhibiting activity, and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| XIONGWEI DONG ET AL.: ""Synthesis, structures and urease inhibition studies of copper(II) and nickel(II) complexes with bidentate N,O-donor Schiff base ligands"", 《JOURNAL OF INORGANIC BIOCHEMISTRY》 * |
| ZHONG-LU YOU ET AL.: ""Synthesis, characterization and crystal structures of a pair of azido-bridged polynuclear Schiff base copper(II) complexes with urease inhibitory activity"", 《TRANSITION MET CHEM》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977505A (en) * | 2017-04-12 | 2017-07-25 | 山东理工大学 | Oxadiazole carboxylic acid metal's complex and its preparation method and application |
| CN106977505B (en) * | 2017-04-12 | 2019-08-13 | 山东理工大学 | Oxadiazoles carboxylic acid metal's complex and its preparation method and application |
| CN108003178A (en) * | 2017-12-22 | 2018-05-08 | 辽宁师范大学 | Acylhydrazone copper (II) complex and preparation method thereof and its application in urease activity is suppressed |
| CN111234257A (en) * | 2020-03-13 | 2020-06-05 | 南昌航空大学 | Schiff base zinc complex functionalized polyion liquid and preparation method and application thereof |
| CN111234257B (en) * | 2020-03-13 | 2021-12-07 | 南昌航空大学 | Schiff base zinc complex functionalized polyion liquid and preparation method and application thereof |
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| CN105061475B (en) | 2017-03-01 |
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