CN105111227B - Schiff base dinuclear cadmium complex and preparation method therefor - Google Patents
Schiff base dinuclear cadmium complex and preparation method therefor Download PDFInfo
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- CN105111227B CN105111227B CN201510493380.1A CN201510493380A CN105111227B CN 105111227 B CN105111227 B CN 105111227B CN 201510493380 A CN201510493380 A CN 201510493380A CN 105111227 B CN105111227 B CN 105111227B
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Abstract
The present invention discloses a schiff base dinuclear cadmium complex and a preparation method therefor, and relates to the technical field of medicines. The complex is a yellow bulk crystal, the chemical name of which is N,N'-di(o-hydroxyl benzylidene)-1,2-phenylenediamine hydrazine cadmium (II), and is named [C23H21N2O4] for short, the molecular formula of which is C46H42Cd2N4O8, the molecular weight is FW=1002.8, and the theoretical value of feature structure parameter (%) is: C,55.05; H, 4.19; N, 5.58, the experimental value is: C, 55.15; H, 4.26; N, 5.61. The complex can be used in antibacterial therapy, has an obvious antibacterial activity, and can bring innovation for the medical field and is strong in practicality.
Description
Technical field：
The present invention relates to one kind has obvious fungistatic effect to being clinically separated staphylococcus aureus and EHEC
Containing cadmium compound and preparation method thereof, belong to medicine technology field.
Background technology：
Infectious diseases is a kind of disease of serious harm human health, is also the major complications in Multiple organs disorders late period
One of with the cause of death.The use of anti-infectives played an important role for treatment infectious diseases.But with anti-infective
The extensive application of medicine, the drug resistance incidence of various antibacterials increases year by year, such as methicillin-resistant staphylococcus MRSA, product
The bacterial strains such as ESBLS Klebsiella Pneumoniaes, pseudomonas aeruginosa, Candida tropicalis, the multidrug resistant problem of bacterium has become the whole world
The focus of concern.The continuous aggravation of bacterial resistance implementations, is that difficulty, the biography of bacterial drug resistance have been deepened in the treatment of such disease
Broadcasting will cause multi-drug resistant bacteria to infect the severe situation that can be cured without medicine with spreading.In order to seek redress, research is devoted to new
Type drug-resistance bacteria medicine is very urgent.
The content of the invention：
For the problems referred to above, the technical problem to be solved in the present invention is to provide a kind of dilute Buddhist alkali Dinuclear cadmium complex and its system
Preparation Method.
A kind of dilute Buddhist alkali Dinuclear cadmium complex of the present invention and preparation method thereof, it is yellow bulk crystals, its chemical name
For double N, referred to as N'- bis- (salicylidene) -1,2- phenylenediamine contractings diamine conjunction cadmium (II), [Cd2(C23H21N2O4)], its molecular formula
C46H42Cd2N4O8, its molecular weight FW=1002.8, the theoretical value of its feature structure parameter (%)：C, 55.05；H, 4.19；N,
5.58, experiment value is：C, 55.15；H, 4.26；N, 5.61.
Preferably, its preparation method is：1st, the o-phenylenediamine for weighing 2mmol (0.2160g) is dissolved in the anhydrous second of 10mL
In alcoholic solution, then weigh the salicylide of 5mmol (0.714g) and be dissolved in 15mL ethanol solutions, will in 60 DEG C of constant temperature oil baths
O-phenylenediamine is added dropwise in salicylide, after being well mixed, is refluxed 4 hours, filtration nothing after the night of cooling and standings one
Water-ethanol is washed three times, and drying is obtained part (0.5634g, yield：75%)；
2nd, the Yi Suan Cadmium of 0.01mmol (0.0316g) parts and 0.01mmol (0.0236g) are weighed respectively, and part is dissolved
In 10mL 1,2- dichloroethane solutions, dissolving metal salts in 2mL ethanol solutions, by second under stirring after being completely dissolved
Suan Cadmium are added dropwise in part, stirring at normal temperature 30min, and filtering and standing obtains measurable yellow crystals after two weeks, and suitable X- is penetrated
Line single crystal diffraction, yield is 80%.
Beneficial effects of the present invention are：It can be used in antibacterial therapy, there is obvious bacteriostatic activity, give medical domain band
It is practical to innovate.
Description of the drawings：
For ease of explanation, the present invention is embodied as and accompanying drawing is described in detail by following.
Fig. 1 is the reacting flow chart of dilute Buddhist alkali Dinuclear cadmium complex preparation process in the present invention,
Fig. 2 is the chemical structural formula of dilute Buddhist alkali Dinuclear cadmium complex in the present invention.
Fig. 3 is the antibacterial circle diameter tables of data of complex extracorporeal bacteria inhibitor test in embodiment；
Fig. 4 is antibacterial circle diameter tables of data of the complex to S. atreus clinical separation strains in embodiment；
Fig. 5 is that S. atreus clinical separation strains are straight to clinical common antibiotics drug sensitive test paper inhibition zone in embodiment
Footpath tables of data；
Fig. 6 is complex in embodiment to being clinically separated EHEC antibacterial circle diameter tables of data；
Fig. 7 is to be clinically separated EHEC to clinical common antibiotics drug sensitive test paper antibacterial circle diameter data in embodiment
Table；
Fig. 8 is complex in embodiment to S. aureus L-forms and its MIC/MBC values of drug-fast bacteria；
Fig. 9 is MIC and MBC value of the complex to large intestine in embodiment.
Specific embodiment：
It is concrete below by what is illustrated in accompanying drawing to make the object, technical solutions and advantages of the present invention of greater clarity
Embodiment is describing the present invention.However, it should be understood that these descriptions are simply exemplary, and it is not intended to limit the model of the present invention
Enclose.Additionally, in the following description, the description to known features and technology is eliminated, to avoid unnecessarily obscuring the present invention's
Concept.
This specific embodiment is employed the following technical solutions：It is yellow bulk crystals, its chemistry entitled couple of N, N'- bis-
(salicylidene) -1,2- phenylenediamine contractings diamine closes cadmium (II), referred to as [Cd2(C23H21N2O4)], its molecular formula C46H42Cd2N4O8,
Its molecular weight FW=1002.8, the theoretical value of its feature structure parameter (%)：C, 55.05；H, 4.19；N, 5.58, experiment value
For：C, 55.15；H, 4.26；N, 5.61.Its chemical structural formula is as shown in Figure 2.
Further, as shown in figure 1, its preparation method is：1st, the o-phenylenediamine for weighing 2mmol (0.2160g) is dissolved in
In 10mL ethanol solutions, then weigh the salicylide of 5mmol (0.714g) and be dissolved in 15mL ethanol solutions, in 60 DEG C of perseverances
O-phenylenediamine is added dropwise in salicylide in warm oil bath, after being well mixed, is refluxed 4 hours, the night of cooling and standings one
Filter afterwards with absolute ethanol washing three times, drying is obtained part (0.5634g, yield：75%)；
2nd, the Yi Suan Cadmium of 0.01mmol (0.0316g) parts and 0.01mmol (0.0236g) are weighed respectively, and part is dissolved
In 10mL 1,2- dichloroethane solutions, dissolving metal salts in 2mL ethanol solutions, by second under stirring after being completely dissolved
Suan Cadmium are added dropwise in part, stirring at normal temperature 30min, and filtering and standing obtains measurable yellow crystals after two weeks, and suitable X- is penetrated
Line single crystal diffraction, yield is 80%.
Embodiment：
Antibody-resistant bacterium is identified
Antibody-resistant bacterium is isolated from the clinical infectious sample of Kunming General Hospital Chengdu Military Area, well-established law Zengjing Granule.S. aureus L-forms strain
Drug resistance is carried out by antibiotic susceptibility traditional test methods (K-B paper disk methods), with the cephalo of (the 17th edition) recommendation of CLSI2007 versions
Western fourth drug sensitive test paper method of operating and criterion confirm.The identification for producing ESBLS EHECs is judged according to the method for document.
Drug-fast bacteria antibiotics susceptibility test
Drug-fast bacteria antibiotics susceptibility test is according to CLSI2007 versions (CLSI, 2007) antibiotic drug sensitive traditional test methods (paper disk method)
Carry out.
Scalping
The method and standard tested according to U.S. clinical in examination standard committee (CLSI) is measured, and tests the previous day,
Normal bacterial to be measured is inoculated in MH culture mediums, fungi and is inoculated in husky guarantor's culture medium, and in 35 DEG C of insulating boxs 18-24h is cultivated, and makes work
Change.With 5%DMSO as solvent, make the dissolution of crystals of complex 1 and be configured to the concentration of 30mg/mL, place stand-by.Again with sterile cotton
It is that 1.5*10^8CFU/ml and standard fungi concentration are 1.0*10^6CFU/mL's that label dip the normal bacterial concentration for having prepared
Bacteria suspension, the corresponding culture medium of uniform application, the liquid for being prepared 50uL with micropipettor (30mg/mL) is added in culture medium
The Kong Zhongzhong accomplished fluently on flat board, puts and cultivate in 35 DEG C of insulating boxs 18-24h, measures inhibition zone size.Make blank right with 5%DMSO
According to.
Drug-fast bacteria is screened and drug sensitive test paper contrast experiment
Choose 6 plants of golden staphylococcis clinical drug-resistant bacterial strain, drug sensitive test paper take minocycline, Cefoxitin, benzyl penicillin,
Vancomycin, levofloxacin, rifampin, TOB；Choose the clinical drug-resistant bacterial strain that 4 plants of large intestines produce ESBLS angstrom of uncommon bacterium, susceptibility
The scraps of paper take Etimicin, Ciprofloxacin, ampicillin, AZT, cefotaxime, safe energy, levofloxacin, cefotaxime/carat
The sour potassium of dimension, the same 1.4.1 of flat board semar technique, preparating liquid concentration is 30mg/mL, and antibacterial activity test is carried out respectively, is measured antibacterial
Circle size.5%DMSO is as a control group.
The measure of minimum inhibitory concentration MIC value
The complex of (antibacterial circle diameter is not less than 10mm) sensitive to antibody-resistant bacterium is chosen, according to U.S. clinical and laboratory
The micro-dilution method that ANSI (CLSI) is recommended is determining MIC value (bacterium M-H meat of the different strains to Different Complex
Soup nutrient solution, fungi Sabouraud liquid medium), every group of operation repetitive 3 times draws mean concentration.Select aseptic 96 hole
Flat-bottom microplates, add 200uL nutrient solutions as negative control in it often ranked first hole；Add in it often ranked second hole
100uL bacterium solutions and 100uL nutrient solutions are used as positive control；Add in each holes of 3-12 nutrient solution 100uL in every row, then in every
Arrange the 3rd hole and add test medicine 100uL, be well mixed, and take out 100uL and move in the 4th hole, by that analogy until the 12nd hole is mixed
100uL is drawn after even to discard, and bacterium (5*10^5CFU/mL) and fungi (1*10^4CFU/ after mixing most are added in each hole
ML bacteria suspension 100ul).Culture plate is placed in 35 DEG C of insulating boxs and cultivates 18h observation results, determine its MIC value.Select black
Background is observed, with the drug concentration in the clear bright least concentration hole of solution as MIC.
The measure of minimum bactericidal concentration MBC values
When it is determined that after MIC value, taking the culture in 3-5 hole before MIC value, transferred species puts 35 DEG C of training on MH agar plates
In foster case, culture 22h or so is rear to take out observation, and lowest concentration of drug of the bacteria colony count averagely less than 5 is defined as the change
The MBC of compound.
The Analysis of Antimicrobial Activity of metal complex
Criterion:Inhibition zone represents that bacteriostasis is weak or without bacteriostatic activity less than 10mm；It is slight sensitive equal to 10mm；
11-15mm is medium sensitivity；It is extremely sensitive more than 16mm.Metal complex is shown in Fig. 3 to the antibacterial result of standard bacteria.
Can determine whether according to Fig. 3 results, complex is to standard staphylococcus aureus, and standard EHEC is sensitive.
Complex is analyzed the bacteriostatic activity of S. atreus clinical separation strains
Antibacterial experiment in vitro adopts the disk diffusion method, bacterial classification used to be：It is clinically separated methicillin-resistant staphylococcus grape ball
Bacterium.Test result such as Fig. 4 and its result such as Fig. 5 antibacterial to the quick scraps of paper of common antibiotics susceptibility.
Complex is analyzed the bacteriostatic activity of Clinical Isolates of Escherichia Coli
Antibacterial experiment in vitro adopts the disk diffusion method, bacterial classification used to be：It is clinically separated large intestine angstrom
Uncommon bacterium.Test result such as Fig. 6 and large intestine drug sensitive test paper inhibition zone such as Fig. 7.
Test result indicate that complex has certain fungistatic effect to producing ESBLs.
Based on the scalping result of standard bacteria, the clinical drug-resistant bacterial strain for choosing respective standard bacterial strain is further tested,
As a result Fig. 4, Fig. 5, Fig. 6, Fig. 7 are seen respectively.Fig. 4 shows that complex is sensitive to most of Staphylococcus aureus antibody-resistant bacterium, enters one
Step analysis result finds that the antibacterial activity of complex has further researching value better than benzyl penicillin and rifampin.Fig. 6 data show
Show, complex is sensitive to Escherichia coli clinical drug-resistant bacterial strain.
Complex is to S. aureus L-forms and the measurement result of the MIC/MBC of large intestine
By the screening of inhibition zone result, choose complex 1 of the antibacterial circle diameter more than 12mm carries out MIC and MBC to it
Measure.Its measurement result is shown in Fig. 8 and Fig. 9：
In this experiment, complex is 15.625～62.5ug/ml to the MIC value of staphylococcus aureus, and MBC values are
31.25～125ug/ml；Complex is 31.25～62.5ug/ml to the MIC value of EHEC, MBC values for 62.5～
125ug/ml；Show that complex has certain fungistatic effect to staphylococcus aureus and EHEC, and to golden yellow
Staphylococcic bacteriostasis is strong compared with EHEC.
The general principle and principal character and advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel it should be appreciated that the present invention is not restricted to the described embodiments, the simply explanation described in above-described embodiment and specification this
The principle of invention, without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, these changes
Change and improvement is both fallen within scope of the claimed invention.The claimed scope of the invention by appending claims and its
Equivalent thereof.
Claims (2)
1. a kind of dilute Buddhist alkali Dinuclear cadmium complex, it is characterised in that：It is yellow bulk crystals, its chemistry entitled couple of N, N'- bis-
(salicylidene) -1,2- phenylenediamine contractings diamine closes cadmium (II), referred to as [Cd2(C23H21N2O4)2], its molecular formula
C46H42Cd2N4O8, its molecular weight FW=1002.8, the theoretical value of its feature structure parameter (%)：C, 55.05；H, 4.19；N,
5.58, experiment value is：C, 55.15；H, 4.26；N, 5.61.
2. the preparation method of a kind of dilute Buddhist alkali Dinuclear cadmium complex according to claim 1, it is characterised in that：(1) weigh
The o-phenylenediamine of 2mmol is dissolved in 10mL ethanol solutions, then weighing the salicylide of 5mmol, to be dissolved in 15mL absolute ethyl alcohols molten
In liquid, o-phenylenediamine is added dropwise in salicylide in 60 DEG C of constant temperature oil baths, after being well mixed, is refluxed 4 hours,
Filter after the night of cooling and standings one with absolute ethanol washing three times, drying is obtained part 0.5634g, yield：75%；
(2) cadmium acetate of 0.01mmol parts and 0.01mmol being weighed respectively, part being dissolved in into 10mL 1,2- dichloroethanes is molten
In liquid, dissolving metal salts are added dropwise to cadmium acetate in part under stirring after being completely dissolved in 2mL ethanol solutions,
Stirring at normal temperature 30min, filtering and standing obtains measurable yellow crystals after two weeks, be adapted to X-ray single crystal diffraction, and yield is 80%.
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Citations (2)
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|---|---|---|---|---|
| CN104352519A (en) * | 2014-11-17 | 2015-02-18 | 云南大学 | Manganese-containing compound for treating diabetes and preparation method thereof |
| CN104447852A (en) * | 2014-11-17 | 2015-03-25 | 云南大学 | Novel schiff base vanadium oxide compound as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104352519A (en) * | 2014-11-17 | 2015-02-18 | 云南大学 | Manganese-containing compound for treating diabetes and preparation method thereof |
| CN104447852A (en) * | 2014-11-17 | 2015-03-25 | 云南大学 | Novel schiff base vanadium oxide compound as well as preparation method and application thereof |
Non-Patent Citations (4)
| Title |
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| "双水杨醛缩邻苯二胺双希夫碱过渡金属(Ni，Cu，Cd) 配合物的合成、结构及其荧光性质研究";梅艳等;《江西化工》;20101215(第4期);第64-68页 * |
| Synthesis of metal complexes involving Schiff base ligand with methylenedioxy moiety: Spectral, thermal, XRD and antimicrobial studies;M L Sundararajan et al.;《Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy》;20140424;第113卷(第15期);第82-93页 * |
| Synthesis, spectral characterization, thermal analysis, molecular modeling and antimicrobial activity of new potentially N2O2 azo-dye Schiff base complexes;S A Aldhlmani et al.;《Journal of Molecular Structure》;20140614(第1074期);第359-375页 * |
| 含吡啶酰胺基双Schiff碱的过渡金属配合物的合成;蔡丽华等;《精细石油化工》;20100331;第27卷(第2期);第16-20页 * |
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