CN103288857A - Sarafloxacin metal complex and preparation method thereof - Google Patents
Sarafloxacin metal complex and preparation method thereof Download PDFInfo
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- CN103288857A CN103288857A CN2013102280727A CN201310228072A CN103288857A CN 103288857 A CN103288857 A CN 103288857A CN 2013102280727 A CN2013102280727 A CN 2013102280727A CN 201310228072 A CN201310228072 A CN 201310228072A CN 103288857 A CN103288857 A CN 103288857A
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- QWPYXHPAENTCCE-UHFFFAOYSA-N NN(OC(c1c2)C3=CN(c(cc4)ccc4F)c1cc(N1CCNCC1)c2F)OC3=O Chemical compound NN(OC(c1c2)C3=CN(c(cc4)ccc4F)c1cc(N1CCNCC1)c2F)OC3=O QWPYXHPAENTCCE-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a sarafloxacin metal complex and a preparation method thereof. The preparation method comprises the following steps of: (1) dissolving sarafloxacin into an organic solvent and ammonia water, mixing the raw materials to adjust the PH value, and then stirring the raw materials to prepare a sarafloxacin solution with the concentration of 0.01-5 mmol.mL<-1>; (2) preparing a metal salt into a metal salt solution with the concentration of 0.05-5 mmol.mL<-1>; (3) dissolving amine and derivatives thereof into the organic solvent to prepare an amine solution with the concentration of 0.05-5 mmol.mL<-1>; and (4) mixing the sarafloxacin solution, the metal salt solution and the amine solution, stirring the solutions at normal temperature, filtering the solutions, stewing the solutions at room temperature to obtain crystals, and washing and drying the crystals to obtain the sarafloxacin metal complex. The preparation method is simple and easy to operate; the sarafloxacin metal complex crystals can be used for preparing helicobacter pylori resistant medicaments; and the yield of the sarafloxacin metal complex is high.
Description
Technical field
The present invention relates to a kind of sarafloxacin metal complexes, be specifically related to a kind of sarafloxacin metal complexes and preparation method thereof.
Technical background
Its structure of sarafloxacin is as follows:
Sarafloxacin (Sarafloxacin) is the fluoroquinolones that first (August 18 nineteen ninety-five) is used for food animal by drugs approved by FDA.For off-white color to light yellow crystalline powder, odorless, mildly bitter flavor, have draw moist.This medicine has a broad antifungal spectrum, sterilizing power are strong, to G
+, G
-Bacterium and Mycoplasma have remarkable effect, and and the antibacterials of other types between do not have cross resistance, still very responsive to the bacterial strain of microbiotic, sulfamido, nitrofuran deposits yields resistance to those.The sarafloxacin commodity are sarafloxacin hydrochloride, its good water solubility, but multipath administration, and absorption rate is fast, and the bioavailability height is the ideal medicament of control livestock and poultry, and it will be at its remarkable anti-microbial effect of veterinary clinic performance.
After sarafloxacin and amine are dissolved in organic solvent, can be further and metal ion generation coordination, form a series of coordination compoundes.Sarafloxacin is as antibacterials, embody it and had suitable marketable value, further its metal complexes of further investigation has certain actual value, especially He Cheng a series of novel sarafloxacin metal complexes and their biological activity is carried out systematic research have very important meaning.
Summary of the invention
The object of the present invention is to provide a kind of sarafloxacin metal complexes and preparation method thereof, the preparation method is simple, easy handling, and product yield height, and the sarafloxacin metal complexes of gained is used for the preparation of medicine for anti Helicobacter pylori.
The metal complexes of sarafloxacin of the present invention is characterized in that having following structural unit:
Wherein: M=Zn, Cu, Mn, Co, Ni, N represent all amines and derivative thereof.
Described sarafloxacin metal complexes preparation process is as follows:
(1) sarafloxacin is dissolved in organic solvent and the ammoniacal liquor, mixing is stirred after regulating pH value, and being made into concentration is 0.01-5mmolmL
-1The sarafloxacin solution for later use;
(2) metal-salt is made solution, being made into concentration is 0.05-5mmolmL
-1Metal salt solution stand-by;
(3) amine and derivative thereof are dissolved in organic solvent, being made into concentration is 0.05-5mmolmL
-1The amine solution for later use;
(4) sarafloxacin solution, metal salt solution and amine solution are mixed, stir under the normal temperature, filter, obtain crystal after room temperature leaves standstill, washing, dried crystals obtain the metal complexes of sarafloxacin.
Wherein, organic solvent is one or more of methyl alcohol, acetonitrile or ethanol, and step (1) can be identical with organic solvent in the step (3), also can be different.
Adjusting PH is 7-13.
Churning time in the step (1) is 5-50min.
Metal-salt is magnesium-yttrium-transition metal salt, preferably copper, cobalt, nickel, zinc or manganese a kind of.
Various amine or derivatives thereofs are N, N-diethyl ethylenediamine, N, N-dimethyl-ethylenediamine, quadrol, 1,3-propylene diamine, 1,2-propylene diamine, one or more of 2-ethylaniline or 2,5-dichlorphenamide bulk powder.
Organic solvent is one or more of methyl alcohol, acetonitrile or ethanol.
The solute mol ratio of sarafloxacin solution, metal salt solution and amine or derivatives thereof solution is 1-3:1-3:1-3.
Churning time is 5min-2h in the step (4).
The solution left standstill time is 2-15 days in the step (4).
Drying temperature is normal temperature in the step (4), and be 1h-24h time of drying.
Experiment showed, that the sarafloxacin metal complexes for the preparation of antimicrobial drug, has restraining effect to urase, can be used in the preparation urease inhibitor.
Compared with prior art, the present invention has following beneficial effect:
Preparation method of the present invention is simple, easy handling, and product yield height.The urase antagonistic action of the sarafloxacin metal complexes crystal that makes is strong, so sarafloxacin metal complexes crystal can be used in the preparation of medicine for anti Helicobacter pylori; And bacteriostatic activity and sarafloxacin are compared itself, and tangible difference is arranged.
Description of drawings
Fig. 1 is that the sarafloxacin of embodiment 1 closes copper (II) crystalline structure figure.
Fig. 2 is that the sarafloxacin of embodiment 2 closes zinc (II) crystalline structure figure.
Embodiment
The present invention will be further described below in conjunction with embodiment, but scope of the present invention is not subjected to any restriction of these embodiment.
Embodiment 1: sarafloxacin closes copper (II)
(1) sarafloxacin 15mmol is dissolved in the mixed solvent of 10mL methyl alcohol and ammoniacal liquor, wherein three's ratio is 1000:1, places the 25mL beaker, and regulating pH with ammoniacal liquor is 9, stirs 10 minutes under the room temperature, is made into to be 1.5mmolmL
-1Concentration stand-by.
(2) with magnesium-yttrium-transition metal mantoquita Cu (ClO
4)
26H
2O makes solution, is made into 2.0mmolmL
-1Concentration stand-by.
(3) with N, N-diethyl ethylenediamine, 2-ethylaniline and 2,5-dichlorphenamide bulk powder are dissolved in methyl alcohol, are made into 3.0mmolmL
-1Solution for later use.
(4) in 1ml sarafloxacin solution, add the 2.0mmolmL for preparing earlier
-1Cu (ClO
4)
26H
2O methanol solution 1mL and 3.0mmolmL
-1N, N-diethyl ethylenediamine methanol solution 1mL stirred under the room temperature 30 minutes, filtered, and left standstill under the room temperature 10 days, a large amount of blue transparent crystalss occurred.Filtration obtains crystal, uses washed with methanol three times, places Calcium Chloride Powder Anhydrous moisture eliminator inner drying 3 hours, obtains sarafloxacin and closes copper (II) 0.9080g, productive rate: 57.80%.Crystalline structure such as Fig. 1.
Embodiment 2: sarafloxacin closes zinc (II)
(1) sarafloxacin 0.1mmol is dissolved in three's ratio is 7:2:1 in the mixed solvent of 10mL methyl alcohol, acetonitrile and ammoniacal liquor, places the 25mL beaker, regulating pH with ammoniacal liquor is 10, stirs 5 minutes under the room temperature, is made into to be 0.01mmolmL
-1Concentration stand-by.
(2) with magnesium-yttrium-transition metal zinc salt Zn (ClO
4)
26H
2O makes solution, is made into 0.05mmolmL
-1Concentration stand-by.
(3) 1,2-the third two is dissolved in methyl alcohol, is made into 0.05mmolmL
-1Solution for later use.
(4) in 2ml sarafloxacin solution, add the 0.05mmolml for preparing earlier
-1Zn (ClO
4)
26H
2O methanol solution 1mL, 0.05mmolmL
-11,2-propylene diamine methanol solution 1mL stirred under the room temperature 5 minutes, filtered, and left standstill under the room temperature 15 days, a large amount of faint yellow transparent crystalss occurred.Filtration obtains crystal, uses washed with methanol three times, places Calcium Chloride Powder Anhydrous moisture eliminator inner drying 10 hours, obtains sarafloxacin and closes zinc (II) 0.0290g, productive rate: 60.26%.Crystalline structure such as Fig. 2.
Embodiment 3: sarafloxacin closes cobalt (II)
(1) sarafloxacin 50mmol is dissolved in three's ratio is 3:2:5 in the mixed solvent of 10mL methyl alcohol, ethanol and ammoniacal liquor, places the 25mL beaker, regulating pH with ammoniacal liquor is 13, stirs 10 minutes under the room temperature, is made into to be 5mmolmL
-1Concentration stand-by.
(2) with magnesium-yttrium-transition metal cobalt salt Co (ClO
4)
26H
2O makes solution, is made into 5mmolmL
-1Concentration stand-by.
(3) 1,3-the third two is dissolved in ethanol, is made into 5mmolmL
-1Solution for later use.
(4) in 1ml sarafloxacin solution, add the 5mmolml for preparing earlier
-1Co (ClO
4)
26H
2O methanol solution 1mL, 5mmolmL
-11,3-propylene diamine ethanolic soln 1mL stirred under the room temperature 1 hour, filtered, and left standstill under the room temperature 15 days, a large amount of red transparent crystalss occurred.Filtration obtains crystal, uses washed with methanol three times, places Calcium Chloride Powder Anhydrous moisture eliminator inner drying 8 hours, obtains sarafloxacin and closes cobalt (II) 2.7480g, productive rate: 61.01%.
Embodiment 4: sarafloxacin closes nickel (II)
(1) sarafloxacin 32mmol is dissolved in the mixed solvent of 10mL methyl alcohol, ethanol, acetonitrile and ammoniacal liquor, four ratios are 4:1:1:4, place the 25mL beaker, and regulating pH with ammoniacal liquor is 8, stir 50 minutes under the room temperature, are made into to be 3.2mmolmL
-1Concentration stand-by.
(2) with magnesium-yttrium-transition metal nickel salt Ni (ClO
4)
26H
2O makes solution, is made into 4.0mmolmL
-1Concentration stand-by.
(3) with N, N-diethyl ethylenediamine and 1,2-propylene diamine are dissolved in acetonitrile, are made into 4.1mmolmL
-1Solution for later use.
(4) in 1ml sarafloxacin solution, add the 4.0mmolmL for preparing earlier
-1Ni (ClO
4)
26H
2O methanol solution 1mL, 4.1mmolL
-1N, N-diethyl ethylenediamine acetonitrile solution 1mL stirred under the room temperature 2 hours, filtered, and left standstill under the room temperature 2 days, a large amount of green transparent crystal occurred.Filtration obtains crystal, uses washed with methanol three times, places Calcium Chloride Powder Anhydrous moisture eliminator inner drying 24 hours, obtains sarafloxacin and closes nickel (II) 2.2776g, productive rate: 60.39%.
Embodiment 5: sarafloxacin closes manganese (II)
(1) sarafloxacin 0.3mmol is dissolved in the mixed solvent of 10mL methyl alcohol, acetonitrile and ammoniacal liquor, ratio is 400:100:1, places the 25mL beaker, and regulating pH with ammoniacal liquor is 7, stirs 20 minutes under the room temperature, is made into to be 0.03mmolmL
-1Concentration stand-by.
(2) with magnesium-yttrium-transition metal manganese salt Mn (ClO
4)
26H
2O makes solution, is made into 0.1mmolmL
-1Concentration stand-by.
(3) with N, the N-dimethyl-ethylenediamine is dissolved in the methanol acetonitrile mixing solutions, and the two ratio is 4:1, is made into 0.1mmolmL
-1Solution for later use.
(4) in 10ml sarafloxacin solution, add the 0.1mmolmL for preparing earlier
-1Mn (ClO
4)
26H
2O methanol solution 1mL, 0.1mmolmL
-1N, N-dimethyl-ethylenediamine methanol solution 1mL stirred under the room temperature 50 minutes, filtered, and left standstill under the room temperature 10 days, a large amount of light brown transparent crystalss occurred.Filtration obtains crystal, uses washed with methanol three times, places Calcium Chloride Powder Anhydrous moisture eliminator inner drying 3 hours, obtains sarafloxacin and closes manganese (II) 0.0537g, productive rate: 58.96%.
Be that sarafloxacin closes the X-ray single crystal diffraction that copper and sarafloxacin close two kinds of crystal of zinc and detects data such as table 1 below.
Table 1 crystal X-ray single crystal diffraction detects data sheet
Be below the sarafloxacin metal complexes to Bacillus subtillis (B.subtilis), staphylococcus aureus (S.aureus), pseudomonas putida (P.putica), the effect of intestinal bacteria (E.coli).
Be below with the different sarafloxacin metal complexess of gained among the mtt assay test implementation example 1-5 at 2ug/mL, 1ug/mL, 0.75ug/mL, 0.5ug/mL, 0.25ug/mL, 0.2ug/mL, the minimum half-inhibition concentration under 8 different concns of 0.1ug/mL and 0.05ug/mL.Wherein establish sarafloxacin and make the reference control group, DMSO: water=1:1 control group.
Test procedure is: get the Bacillus subtillis (B.subtili s) of cultivation, and staphylococcus aureus (S.aureus), the bacterial strain of pseudomonas putida (P.putica) and intestinal bacteria (E.coli) is diluted to 2 * 10 respectively
4Individual/mL, be sub-packed in 96 orifice plates, orifice plate is the 0.1mL/ hole.Every hole 10 μ L.Each group is established 3 parallel holes, puts in 37 ℃ of constant incubators and cultivates 24h, squeezes into the MTT liquid 10 μ L/ holes of 5mg/mL, cultivates 4h again.Take out culture plate, centrifugal, outwell supernatant liquid, add DMSO150 μ L/ hole, under the 570nm wavelength, measure the OD value with BioRad550 type microplate reader produced in USA, calculate the bacterial growth inhibiting rate by following formula, i.e. minimum half-inhibition concentration, MICs.
Growth inhibition ratio=(the average OD value of the average OD value/control group of 1-medication group) * 100%
Minimum half-inhibition concentration is more little, and the germ resistance of compound is more good, bacteriostatic activity test result such as the table 2 of different sarafloxacin metal complexess among sarafloxacin and the embodiment 1-5.
The bacteriostatic activity table with test results of different sarafloxacin metal complexess among table 2 sarafloxacin and the embodiment 1-5
The result shows: the sarafloxacin metal complexes is to Bacillus subtillis (B.subtilis), staphylococcus aureus (S.aureus), pseudomonas putida (P.putida) and intestinal bacteria (E.coli) have restraining effect in various degree, and bacteriostatic action has been compared bigger variation than sarafloxacin.
Be the active test of urase inhibition to sarafloxacin metal complexes, sarafloxacin and the N-acetylhydroxylamine of embodiment 1-5 gained below.
Test procedure is: add the huge beans urase of 25 μ L10kU/L solution in 96 well culture plates respectively, the sarafloxacin that adds 25 μ L concentration more respectively and be embodiment 1 gained of 10 μ M, 5 μ M, 2.5 μ M, 1.25 μ M closes the sample solution of copper, cultivate after 1 hour for 37 ℃, add 200 μ L100mM HEPES damping fluids, record pH rises to the 7.7 o'clock used time (phenol red developer variable color) by 6.8, and under the 570nm wavelength, detect the OD value with microplate reader, calculate enzyme inhibiting rate IC50 alive, test-results such as table 3.
With identical testing method embodiment 2-4, sarafloxacin and N-acetylhydroxylamine are carried out antiurease active testing, test-results such as table 3.
Wherein, DMSO:H in the sample solution
2O=1:1; The pH of damping fluid is 6.8, includes 500mM urea and 0.002% phenol red; N-acetylhydroxylamine is as positive control.
Enzyme inhibiting rate alive=(T sample-T blank)/T sample.
The urase of table 3 sarafloxacin metal complexes, sarafloxacin and N-acetylhydroxylamine suppresses active table
The result shows that it is embodiment 1 that the urase of sarafloxacin metal complexes suppresses active order〉embodiment 5〉embodiment 3〉embodiment 4〉embodiment 2〉sarafloxacin.The present invention is active strong to the inhibition of urase than sarafloxacin.
Claims (10)
1. a sarafloxacin metal complexes is characterized in that, sarafloxacin metal complexes structural unit is as follows:
Wherein: M=Zn, Cu, Mn, Co, Ni, N represent all amines and derivative thereof.
2. the preparation method of the described sarafloxacin metal complexes of claim 1 is characterized in that step is as follows:
(1) sarafloxacin is dissolved in organic solvent and the ammoniacal liquor, mixing is stirred after regulating pH value, and being made into concentration is 0.01-5mmolmL
-1The sarafloxacin solution for later use;
(2) magnesium-yttrium-transition metal salt is soluble in water, being made into concentration is 0.05-5mmolmL
-1Metal salt solution stand-by;
(3) amine and derivative thereof are dissolved in organic solvent, being made into concentration is 0.05-5mmolmL
-1Amine and derivative solution thereof stand-by;
(4) sarafloxacin solution, metal salt solution and amine solution are mixed, stir under the normal temperature, filter, obtain crystal after room temperature leaves standstill, washing, dried crystals obtain the metal complexes of sarafloxacin.
3. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, organic solvent is one or more of methyl alcohol, acetonitrile or ethanol.
4. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, adjusting PH is 7-13.
5. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, the churning time in the step (1) is 5-50min.
6. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, magnesium-yttrium-transition metal salt is a kind of of copper, cobalt, nickel, zinc or manganese.
7. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, various amine or derivatives thereofs are N, the N-diethyl ethylenediamine, N, N-dimethyl-ethylenediamine, quadrol, 1, the 3-propylene diamine, 1,2-propylene diamine, one or more of 2-ethylaniline or 2,5-dichlorphenamide bulk powder.
8. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, the solute mol ratio of sarafloxacin solution, metal salt solution and amine or derivatives thereof solution is 1-3:1-3:1-3.
9. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, churning time is 5min-2h in the step (4).
10. the preparation method of sarafloxacin metal complexes according to claim 2 is characterized in that, the solution left standstill time is 2-15 days in the step (4); Drying temperature is normal temperature, and be 1h-24h time of drying.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804393A (en) * | 2014-01-28 | 2014-05-21 | 广西师范大学 | Marbofloxacin rare-earth chelates as well as synthetic method and application thereof |
| CN104370855A (en) * | 2014-09-22 | 2015-02-25 | 山东理工大学 | Bis-(p-fluorophenyl)methylpiperazine acetic acid coordination compound and preparation method thereof |
| CN110463719A (en) * | 2018-12-29 | 2019-11-19 | 黑龙江大学 | Ciprofloxacin metal complex-polyalkenylalcohols compound and its preparation method and application |
| CN113075147A (en) * | 2021-02-26 | 2021-07-06 | 南开大学滨海学院 | Sasa class magnesium metal organic complex material, preparation method thereof and application of material in detecting sulfur-containing malodorous substances |
-
2013
- 2013-06-08 CN CN201310228072.7A patent/CN103288857B/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 任祥祥 等: "诺氟沙星-铜(II)-TBZ/HPB配合物的合成、抗菌活性及与DNA作用", 《化学通报》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804393A (en) * | 2014-01-28 | 2014-05-21 | 广西师范大学 | Marbofloxacin rare-earth chelates as well as synthetic method and application thereof |
| CN104370855A (en) * | 2014-09-22 | 2015-02-25 | 山东理工大学 | Bis-(p-fluorophenyl)methylpiperazine acetic acid coordination compound and preparation method thereof |
| CN110463719A (en) * | 2018-12-29 | 2019-11-19 | 黑龙江大学 | Ciprofloxacin metal complex-polyalkenylalcohols compound and its preparation method and application |
| CN113075147A (en) * | 2021-02-26 | 2021-07-06 | 南开大学滨海学院 | Sasa class magnesium metal organic complex material, preparation method thereof and application of material in detecting sulfur-containing malodorous substances |
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