CN104557988A - Nitrogen heterocyclic Schiff base silver complex as well as preparation method and application thereof - Google Patents
Nitrogen heterocyclic Schiff base silver complex as well as preparation method and application thereof Download PDFInfo
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- CN104557988A CN104557988A CN201510044986.7A CN201510044986A CN104557988A CN 104557988 A CN104557988 A CN 104557988A CN 201510044986 A CN201510044986 A CN 201510044986A CN 104557988 A CN104557988 A CN 104557988A
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Abstract
The invention relates to a Schiff base and specifically relates to a nitrogen heterocyclic Schiff base silver complex as well as a preparation method and an application thereof. The nitrogen heterocyclic Schiff base silver complex is a one-dimensional chained compound and has a structural motif as shown in the specification, wherein L represents SO3CF3- or SbF6-; S represents CHCl3 or CH2Cl2. The preparation method comprises the following steps: mixing 2-picolinyl hydrazide, 2-acetylpyrazine and formic acid together, adding ethanol and heating for reflux, and then cooling and filtering to obtain 2-picolinyl hydrazide acetylpyrazine; next, dissolving the 2-picolinyl hydrazide acetylpyrazine in trichloromethane or dichloromethane, dissolving silver triflate or silver hexafluoroantimonate in methanol, reacting at a normal temperature, and standing in a dark place, thereby obtaining the nitrogen heterocyclic Schiff base silver complex. The complex is simple to synthesize, convenient to purify, relatively high in yield and good in stability in air. Compared with a nitrogen heterocyclic Schiff base ligand, the complex has broad-spectrum antibacterial activity and is remarkably improved in antibacterial properties.
Description
Technical field
The present invention relates to schiff bases, be specifically related to a kind of nitrogen heterocyclic schiff bases silver complex and its preparation method and application.
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 the substituting group changing linking group, be symmetric to asymmetric, chain is to the Shiff base derivative of each spline structures such as ring-type.Schiff bases has stronger coordination ability, can form stable title complex with most metal ion in periodictable.Nitrogenous heterocyclic 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.Polyhedron 2014,67,11-18; Lee, S.M.; Ali, H.M.; Sim, H.M.; Malek, S.N.A.; Lo, K.K.Inorg.Chim.Acta 2013,406,272-278. discloses the application of nitrogen heterocyclic presence of Schiff-base complex at functional materials and pharmaceutical field.
Multiple parasitic bacteria, as the infection that streptococcus aureus, Pseudomonas aeruginosa, intestinal bacteria etc. cause, causes large-scale damage to tissue, and causes the disease of numerous threat human life.The appearance of natural antibacterial medicine and synthesising bacteria anti-reflecting medicine makes effectively to treat various bacteriological infection becomes possibility, for ensureing that human health has made outstanding contribution.But along with the widespread use of synthesising bacteria anti-reflecting medicine clinically, bacterial drug resistance increases year by year, causes the curative effect of some medicines to reduce, even invalid.The appearance of these situations, an urgent demand people constantly provide novel antibacterial medicine.Silver is the bactericidal metal being only second to mercury, and silver and title complex thereof have very long history as antiseptic-germicide.Silver still has very strong anti-microbial activity at low concentrations, and has the performance of low toxicity.Therefore the title complex of silver has good application prospect in antibacterials field, carry out to this furtheing investigate that there is certain theory and actual value, especially synthesis of azacyclic schiff bases silver complex systematic research tool is carried out to their biological activity be of great significance.
Summary of the invention
The object of this invention is to provide a kind of nitrogen heterocyclic schiff bases silver complex prepared for antibacterials, synthesis is simple, and be convenient to purify, productive rate is higher, and property stable in the air is good; The present invention provides its preparation method and application simultaneously.
Nitrogen heterocyclic schiff bases silver complex of the present invention is one-dimensional chain compound, and its structural motif is as follows:
Wherein: L is SO
3cF
3 -or SbF
6 -; S is CHCl
3or CH
2cl
2.
The preparation method of described nitrogen heterocyclic schiff bases silver complex, comprises the following steps:
(1) 2-pyridinecarboxylic hydrazine, 2-ethanoyl pyrazine and formic acid are mixed, add alcohol heating reflux, after reaction terminates, be cooled to room temperature, filter, obtain the nitrogen heterocyclic schiff bases solid-2-pyridinecarboxylic hydrazine contracting acetylpyrazine of white;
(2) 2-pyridinecarboxylic hydrazine contracting acetylpyrazine is dissolved in trichloromethane or methylene dichloride, and metal silver salt is dissolved in methyl alcohol, lucifuge after above-mentioned solution mixing is left standstill, obtains nitrogen heterocyclic schiff bases silver complex; Described metal silver salt is silver triflate or silver hexafluoroantimonate.
Wherein, in step (1), the usage ratio of 2-pyridinecarboxylic hydrazine, 2-ethanoyl pyrazine, formic acid, ethanol is 1 ~ 1.5:1 ~ 1.5:0.08 ~ 0.1:4 ~ 6; 2-pyridinecarboxylic hydrazine and 2-ethanoyl pyrazine are in mmole number, and formic acid and ethanol are in milliliter; In step (1), the reflux time is 4-6 hour.
In step (2), the usage ratio of 2-pyridinecarboxylic hydrazine contracting acetylpyrazine, metal silver salt, trichloromethane or methylene dichloride, methyl alcohol is 1 ~ 1.5:1 ~ 1.5:125 ~ 180:125 ~ 200; 2-pyridinecarboxylic hydrazine contracting acetylpyrazine and metal silver salt are in mmole number, and trichloromethane, methylene dichloride and methyl alcohol are in milliliter; In step (2), lucifuge time of repose is 5-7 days.
Reaction equation of the present invention is as follows:
Nitrogen heterocyclic schiff bases silver complex of the present invention is used for the preparation of antibacterials.
The present invention infrared, ultimate analysis (C, H, N), X-ray single crystal diffraction characterize and confirm the structure of nitrogen heterocyclic schiff bases silver complex.
Nitrogen heterocyclic schiff bases silver complex of the present invention has spectrum antibacterial activity, 5.53 μ g/mL are respectively to the half-inhibition concentration of the subtilis in gram-positive microorganism, 7.88 μ g/mL, the half-inhibition concentration of staphylococcus aureus is respectively 4.90 μ g/mL, 5.95 μ g/mL; 6.66 μ g/mL are respectively to half-inhibition concentration colibacillary in Gram-negative bacteria, 7.91 μ g/mL, 3.76 μ g/mL are respectively to the half-inhibition concentration of Pseudomonas aeruginosa, 2.69 μ g/mL.
Compared with prior art, the present invention has following beneficial effect:
Nitrogen heterocyclic schiff bases silver 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.Compared with nitrogen heterocyclic Schiff base ligand, title complex of the present invention has spectrum antibacterial activity, and its anti-microbial property significantly improves, and antibacterial ability is suitable with positive control medicine.
Accompanying drawing explanation
Fig. 1 is the single crystal structure figure of the embodiment of the present invention 1 title complex;
Fig. 2 is the single crystal structure figure of the embodiment of the present invention 2 title complex.
Embodiment
Below in conjunction with embodiment, the present invention is described further.
Detecting instrument in embodiment is: Perkin-Elmer 240C type elemental analyser, Vector22Bruker spectrophotometer (400-4000cm
-1), Bruker Smart Apex CCD single crystal diffractometer and BioRad 550 type microplate reader etc.
Embodiment 1
The preparation method that 2-pyridinecarboxylic hydrazine contracting acetylpyrazine closes silver triflate is as follows:
(1) by 2-pyridinecarboxylic hydrazine (1.64g, 12mmol), 2-ethanoyl pyrazine (1.46g, 12mmol), the formic acid of 1.0 milliliters is dissolved in 48mL ethanol, heating reflux reaction 5 hours, be cooled to room temperature, the sedimentation and filtration produced, white solid 2-pyridinecarboxylic hydrazine contracting acetylpyrazine 2.69g washed to obtain by ethanol, productive rate: 93%; Compound is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3311,2361,1702,1589,1511,1469,1424,1364,1272,1227,1153,1038,1013,993,907,852,814,751,697,617,473.
Results of elemental analyses: calculated value (%): C, 59.74; H, 4.59; N, 29.03; Measured value (%): C, 59.86; H, 4.57; N, 29.12%;
(2) by 2-pyridinecarboxylic hydrazine contracting acetylpyrazine (9.6mg, 0.04mmol) be dissolved in 5mL trichloromethane, add silver triflate (10.3mg, in 5mL methanol solution 0.04mmol), lucifuge leaves standstill 5 days, occurs 17.8mg light yellow crystal, filters, and by methanol wash three times, be placed in Calcium Chloride Powder Anhydrous moisture eliminator inner drying and obtain product.Productive rate 72%.Product is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3321,3089,2361,1690,1622,1590,1512,1471,1429,1251,1166,1030,911,882,755,700,639,516.
Results of elemental analyses: calculated value (%): C, 27.23; H, 1.96; N, 11.34; Measured value (%): C, 27.31; H, 1.95; N, 11.36.
The structural formula that 2-pyridinecarboxylic hydrazine contracting acetylpyrazine closes silver triflate is as follows:
Wherein: L is SO
3cF
3 -; S is CHCl
3.The character such as above-mentioned complex molecule formula, proterties, productive rate are in table 1.
Embodiment 2
The preparation method that 2-pyridinecarboxylic hydrazine contracting acetylpyrazine closes silver hexafluoroantimonate is as follows:
(1) with embodiment 1 step (1);
(2) by 2-pyridinecarboxylic hydrazine contracting acetylpyrazine (9.6mg, 0.04mmol) be dissolved in 5mL methylene dichloride, add silver hexafluoroantimonate (13.7mg, in 5mL methanol solution 0.04mmol), lucifuge leaves standstill 7 days, occurs 16.8mg light yellow crystal, filters, and by methanol wash three times, be placed in Calcium Chloride Powder Anhydrous moisture eliminator inner drying and obtain product.Productive rate 63%.Product is verified through infrared, ultimate analysis, and result shows that structure is correct, and data are as follows:
Infrared (KBr, cm
-1): 3312,2361,1704,1513,1471,1427,1356,1277,1232,1154,997,910,855,816,753,664,618.
Results of elemental analyses: calculated value (%): C, 23.31; H, 1.96; N, 10.46; Measured value (%): C, 23.35; H, 1.94; N, 10.50.
2-pyridinecarboxylic hydrazine contracting acetylpyrazine closes the structural formula of silver hexafluoroantimonate as embodiment 1, and difference is: L is SbF
6 -; S is CH
2cl
2.The character such as above-mentioned complex molecule formula, proterties, productive rate are in table 1.
The silver complex of table 1 two kinds of nitrogen heterocyclic schiff bases
| Sequence number | Metal-salt | Title complex | Proterties | Productive rate (%) |
| Embodiment 1 | AgSO 3CF 3 | (C 14H 12O 4N 5Cl 3F 3S)Ag | Light yellow crystal | 72 |
| Embodiment 2 | AgSbF 6 | (C 13H 13ON 5Cl 2F 6Sb)Ag | Light yellow crystal | 63 |
Below the title complex that embodiment 1 ~ 2 obtains is detected.
1, the single crystal structure of nitrogen heterocyclic schiff bases silver complex characterizes:
Testing tool is Bruker Smart Apex CCD single crystal diffractometer, with Mo-K α (λ=0.071073nm) ray, tests 20 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 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, nitrogen heterocyclic schiff bases silver complex of the present invention is to Bacillus subtillis (B.subtilis), staphylococcus aureus (S.aureus), the effect of Pseudomonas aeruginosa (P.aeruginosa) and intestinal bacteria (E.coli) detects.
Testing method and step: the Bacillus subtillis (B.subtilis) of getting cultivation, staphylococcus aureus (S.aureus), the bacterial strain of Pseudomonas aeruginosa (P.Aeruginosa) and intestinal bacteria (E.coli), is diluted to 2 × 10 respectively
4individual/mL, is sub-packed in 96 orifice plates, and orifice plate is 0.1mL/ hole, every hole 10 μ L.Establish 3 parallel holes for each group, put in 37 DEG C of constant incubators and cultivate 24h, add the MTT liquid 40 μ L/ hole of 5mg/mL, then cultivate 4h.Take out culture plate, centrifugal, outwell supernatant liquid, add DMSO 150 μ L/ hole, under 570nm wavelength, measure OD value by BioRad 550 type microplate reader, calculate different nitrogen heterocyclic schiff bases silver complex half-inhibition concentration, its streptomycin is as positive control.
Half-inhibition concentration is less, shows that the germ resistance of compound is better, and the bacteriostatic activity test result of raw material, embodiment 1 ~ 2 title complex, control group and blank group is as table 3.
Table 3 bacteriostatic activity table with test results
Claims (7)
1. a nitrogen heterocyclic schiff bases silver complex, it is characterized in that one-dimensional chain compound, and its structural motif is as follows:
Wherein: L is SO
3cF
3 --or SbF
6 --; S is CHCl
3or CH
2cl
2.
2. a preparation method for nitrogen heterocyclic schiff bases silver complex according to claim 1, is characterized in that comprising the following steps:
(1) 2-pyridinecarboxylic hydrazine, 2-ethanoyl pyrazine and formic acid are mixed, add alcohol heating reflux, after reaction terminates, be cooled to room temperature, filter, obtain the nitrogen heterocyclic schiff bases solid-2-pyridinecarboxylic hydrazine contracting acetylpyrazine of white;
(2) 2-pyridinecarboxylic hydrazine contracting acetylpyrazine is dissolved in trichloromethane or methylene dichloride, and metal silver salt is dissolved in methyl alcohol, lucifuge after above-mentioned solution mixing is left standstill, obtains nitrogen heterocyclic schiff bases silver complex; Described metal silver salt is silver triflate or silver hexafluoroantimonate.
3. the preparation method of nitrogen heterocyclic schiff bases silver complex according to claim 2, is characterized in that: in step (1), the usage ratio of 2-pyridinecarboxylic hydrazine, 2-ethanoyl pyrazine, formic acid, ethanol is 1 ~ 1.5:1 ~ 1.5:0.08 ~ 0.1:4 ~ 6; 2-pyridinecarboxylic hydrazine and 2-ethanoyl pyrazine are in mmole number, and formic acid and ethanol are in milliliter.
4. the preparation method of nitrogen heterocyclic schiff bases silver complex according to claim 2, is characterized in that: in step (1), the reflux time is 4-6 hour.
5. the preparation method of nitrogen heterocyclic schiff bases silver complex according to claim 2, is characterized in that: in step (2), the usage ratio of 2-pyridinecarboxylic hydrazine contracting acetylpyrazine, metal silver salt, trichloromethane or methylene dichloride, methyl alcohol is 1 ~ 1.5:1 ~ 1.5:125 ~ 180:125 ~ 200; 2-pyridinecarboxylic hydrazine contracting acetylpyrazine and metal silver salt are in mmole number, and trichloromethane, methylene dichloride and methyl alcohol are in milliliter.
6. the preparation method of nitrogen heterocyclic schiff bases silver complex according to claim 2, is characterized in that: in step (2), lucifuge time of repose is 5 ~ 7 days.
7. a purposes for nitrogen heterocyclic schiff bases silver complex according to claim 1, is characterized in that: nitrogen heterocyclic schiff bases silver complex is used for the preparation of antibacterials.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108424467A (en) * | 2018-04-16 | 2018-08-21 | 陕西科技大学 | A kind of preparation method of cellulose base composite antibacterial material |
| US10556886B2 (en) | 2016-07-29 | 2020-02-11 | Lg Chem, Ltd. | Metal-organic hybrid structures built with multi-directional polydentate ligands |
| US10562845B2 (en) | 2016-07-29 | 2020-02-18 | Lg Chem, Ltd. | Multi-directional polydentate ligands for metal-organic hybrid structures |
| CN114230583A (en) * | 2021-12-09 | 2022-03-25 | 江苏海洋大学 | Binuclear copper complex with biological activity, preparation method and application |
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2015
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Non-Patent Citations (3)
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| AMITABHA DATTA ET AL.: "End-to-end thiocyanato-bridged zig-zag polymers of CuII,CoIIand NiII with a hydrazone ligand: EPR, magnetic susceptibility and biological study", 《POLYHEDRON》, vol. 44, 2 June 2012 (2012-06-02), pages 77 - 87 * |
| SAMIR ALGHOOL ET AL.: "Supramolecular structures of mononuclear and dinuclear", 《POLYHEDRON》, 5 September 2013 (2013-09-05), pages 11 - 18, XP 028797046, DOI: doi:10.1016/j.poly.2013.08.059 * |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10556886B2 (en) | 2016-07-29 | 2020-02-11 | Lg Chem, Ltd. | Metal-organic hybrid structures built with multi-directional polydentate ligands |
| US10562845B2 (en) | 2016-07-29 | 2020-02-18 | Lg Chem, Ltd. | Multi-directional polydentate ligands for metal-organic hybrid structures |
| CN108424467A (en) * | 2018-04-16 | 2018-08-21 | 陕西科技大学 | A kind of preparation method of cellulose base composite antibacterial material |
| CN114230583A (en) * | 2021-12-09 | 2022-03-25 | 江苏海洋大学 | Binuclear copper complex with biological activity, preparation method and application |
| CN114230583B (en) * | 2021-12-09 | 2023-09-08 | 江苏海洋大学 | Binuclear copper complex with bioactivity, preparation method and application |
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