CN103159644A - Curcuminoid condensed aromatic amine Schiff base derivative, as well as preparation method and application thereof in preparation of antibacterial medicaments - Google Patents
Curcuminoid condensed aromatic amine Schiff base derivative, as well as preparation method and application thereof in preparation of antibacterial medicaments Download PDFInfo
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Abstract
The invention relates to a curcuminoid condensed aromatic amine Schiff base derivative, as well as a preparation method and an application thereof in preparation of antibacterial medicaments, belonging to the technical field of synthesized curcuminoid condensed 3, 5-diaromatic amine Schiff base derivatives and applications thereof. According to the technical scheme, the preparation method comprises the following steps: dissolving substituted aromatic amine in anhydrous ethanol, adding a catalytic amount of formic acid and anhydrous aluminum trichloride, stirring, dropwise adding a curcuminoid analog ethanol solution prepared by the above reaction, and protecting with nitrogen; and refluxing and separating a reactant through a silica gel chromatographic method to get a target product. The curcuminoid condensed aromatic amine Schiff base derivative is used for preparing the antibacterial medicaments and used for resisting staphylococcus aureus and streptococcus. The curcuminoid condensed aromatic amine Schiff base derivative disclosed by the invention has an obvious inhibiting effect on the Staphylococcus aureus and the streptococcus; and compared with curcumin wich is a parent body, the curcuminoid condensed aromatic amine Schiff base derivative has the advantages that the antibacterial effect is better, the antibacterial effective time is longer, and the bioavailability and the antibacterial activity are improved.
Description
Technical field
The present invention relates to a kind of curcuminoids contracting aromatic amine Shiff base derivative and preparation method thereof and in the application of preparation antibacterials, belong to synthetic curcuminoids contracting 3,5-two aromatic amine Shiff base derivatives with and uses thereof technical field.
Background technology
Turmeric derives from the rhizome of zingiberaceous plant turmeric (Curcumalonga L), therefrom be separated to first the yellow substance turmeric yellow in 1842, curcumine [curcumin, chemical name: 1,7-two (4-hydroxy-3-methoxy) phenyl-1,6-heptadiene-3, the 5-diketone ］ be its main effective constituent.The chemical structure of curcumine in 1910 is identified first.Research finds, that curcumine has is anti-oxidant, anti-inflammatory, anti-freezing, lipopenicillinase, atherosclerosis, anti-ageing, eliminate free radical and suppress the biological activitys such as tumor growth.But, due to the curcumine poorly water-soluble, especially unstable to the alkaline pH value condition in neutrality, after while curcumine oral absorption, rapidly by liver metabolism, it is obvious that head crosses the elimination phenomenon, and bioavailability is low, so curcumine is carried out suitable structure of modification, to improve its bioavailability and drug effect, therefore, curcumine is carried out structure of modification or synthetic curcumin analogue just becomes Chinese scholars research outline.Having the structural modification of curcumine wherein: (1) is modified two carbonyls of curcumine, synthetic metal complexes etc., for example: publication number is the Chinese patent " application of curcumine-zn cpds in the antibacterial analgesic of preparation or Health Care " of CN101904835A, illustrate that curcumine-zn cpds has good drug effect on analgesia is antibacterial, overcome in the treatment of existing geriatric disease the applicable disease of ubiquity medicine single, the problem that curative effect is desirable not to the utmost; (2) synthetic to the replacement of active methylene group in the curcumine structure is also study hotspot, as publication number CN101434525A Chinese patent " 4-(4-hydroxy 3-methoxybenzene methyl) curcumine and for the preparation of the application of antitumor drug ", synthetic antitumor drug can significantly suppress the propagation of various human tumour cell; (3) to the modification of benzene ring substitution group, United States Patent (USP): US2007204412 (A1) Curcumin and its derivatives for use as silscone colorants, introduce the silane substituted base on the phenolic hydroxyl group of curcumine, painted for silicon materials such as silicon tree elastomericss.
In addition, schiff bases can form title complex by coordinate bond with many metal ions as the important organic ligand of a class, therefore is widely used in pharmacy, catalysis, analytical chemistry, corrosion and photochromic field.Synthesize first schiff bases by people such as Peiifer in 1931, and just really begin to be subject to the attention of chemist the sixties in 20th century, especially in recent years, because some schiff bases has special physiologically active, more and more cause the attention of the world of medicine.It is reported, that the title complex of amino acids, semicarbazone class, contracting amine, heterocyclic, hydrazone class schiff bases and application thereof has is antibacterial, sterilization, unique medicinal effect such as antitumor, antiviral.Therefore, how improving bioavailability and drug effect, is one of technical problem of needing to be resolved hurrily of this area.
Summary of the invention
The object of the invention be to provide a kind of curcuminoids contracting aromatic amine Shiff base derivative and preparation method thereof and the preparation antibacterials application, by synthetic curcumin analogue 1,7-two (4-dimethylin) phenyl-1,6-heptadiene-3,5-diketone ］, again in molecule 3,5-diketone position and bimolecular aromatic amine carry out condensation reaction, form curcuminoids contracting 3,5-two aromatic amine Shiff base derivatives, and the preparation antibacterials, improve bioavailability and anti-microbial activity, solve the problems referred to above that background technology exists.
Technical scheme of the present invention is:
A kind of curcuminoids contracting aromatic amine Shiff base derivative, its structural formula is:
Wherein R is one of fluorine, chlorine, bromine, iodine, hydroxyl, methoxyl group, alkyl, and the R base is the neighbour of phenyl ring, to a, position; Have two or more different groups on phenyl ring, the group relative position be connect,, contraposition.
A kind of preparation method of curcuminoids contracting aromatic amine Shiff base derivative, comprise following steps: with the substituted aromatic amine anhydrous alcohol solution, add formic acid, the aluminum trichloride (anhydrous) of catalytic amount, stir, drip the curcumin analogue ethanolic soln of above-mentioned reaction preparation, nitrogen protection; Reflux, reactant separates with the method for silica gel column chromatography, namely obtains target product.
Step more specifically: be mixed in boron trioxide, methyl ethyl diketone and tributyl borate in three-necked flask and use nitrogen protection, back flow reaction, obtain methyl ethyl diketone and boron trioxide complex compound, then add DMF, 4-dimethylin phenyl aldehyde, n-Butyl Amine 99 reaction, after finishing, adjust pH is 7, the washing organic phase is separated to get the yellow powder product with thin-layer chromatography, is target product; Its reaction process signal formula is as follows:
A kind of curcuminoids contracting aromatic amine Shiff base derivative prepares antibacterials in the application of preparation antibacterials with above-mentioned curcumine contracting aromatic amine Shiff base derivative.
The antibacterials of preparation are used for anti-Staphylococcus aureus, suis or other malignant bacteria.
Positively effect of the present invention: by synthetic curcumin analogue 1,7-two (4-dimethylin) phenyl-1,6-heptadiene-3,5-diketone ］, again in molecule 3,5-diketone position and bimolecular aromatic amine carry out condensation reaction, form curcuminoids contracting 3,5-two aromatic amine Shiff base derivatives, and the preparation antibacterials, improving bioavailability and anti-microbial activity, the compounds of this invention all has obvious restraining effect to streptococcus aureus, suis, with parent curcumine ratio, fungistatic effect is better and antibacterial working lipe is longer.
Description of drawings
Fig. 1 compound title of the present invention and corresponding molecular structure;
Fig. 2 is embodiment of the present invention reaction formula.
Embodiment
Below in conjunction with accompanying drawing, the present invention will be further described by embodiment.
Embodiment 1: curcuminoids derivative 1,7-two (4-dimethylaminophenyl)-3,5-two (4-fluorobenzene imino-)-1,6-heptadiene (DAEF) synthetic.
The 4-fluoroaniline that adds 2mmol in there-necked flask; the 5mL anhydrous alcohol solution; then the formic acid and the aluminum trichloride (anhydrous) that add catalytic amount; under stirring; slowly drip the above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 12mL dehydrated alcohol; heating reflux reaction; the thin-layer chromatography detection reaction was reacted in nitrogen protection 15 hours; after reaction finishes; extract organic phase, concentrated, separate (sherwood oil: ethyl acetate=2:1) with silica gel thin-layer chromatography; obtain yellow solid product, productive rate is 12.4%.And by FTIR, MALDI-TOP,
1The methods such as HNMR have confirmed the structure of this compound.IR (KBr) ν: 3046,2982,2841,1645,1633,1500-1600,1355,1233cm
-1Mass spectrum MALDI-TOF m/z:549 (M+H)
+;
1HNMR (CDCl
3, 400 MHz) and δ: 1.65 (s, 2H ,-CH
2-), 3.14 (s, 12H, N-CH
3), 5.20-6.20 (d, 4H, HC=CH-Ar), 6.88-7.76 (m, 16H, H-Ar).Molecular formula C
35H
34F
2N
4Ultimate analysis calculated value: C 76.62; H 6.25; F 6.93; N 10.21.Measured value C 76.50; H 6.37; F 6.81; N 10.32.
Embodiment 2: curcuminoids derivative 1,7-two (4-dimethylaminophenyl)-3,5-two (4-chlorobenzene imino-)-1,6-heptadiene (DAECl) synthetic.
The 4-chloroaniline that adds 2mmol in there-necked flask; the 5mL anhydrous alcohol solution; then the formic acid and the aluminum trichloride (anhydrous) that add catalytic amount; under stirring; slowly drip the above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 15mL dehydrated alcohol; heating reflux reaction; the thin-layer chromatography detection reaction was reacted in nitrogen protection 8 hours; after reaction finishes; extract organic phase, concentrated, separate (sherwood oil: ethyl acetate=3:1) with silica gel thin-layer chromatography; obtain yellow solid product, productive rate is 22.7%.And by FTIR, MALDI-TOP,
1The methods such as HNMR have confirmed the structure of this compound.IR (KBr) ν: 3036,2979,2839,1642,1631,1490-1580,1350,733cm
-1Mass spectrum MALDI-TOF m/z:581 (M+H)
+;
1HNMR (CDCl
3, 400 MHz) and δ: 1.60 (s, 2H ,-CH
2-), 3.12 (s, 12H, N-CH
3), 5.09-6.14 (d, 4H, HC=CH-Ar), 6.54-7.56 (m, 16H, H-Ar).Molecular formula C
35H
34Cl
2N
4Ultimate analysis calculated value: C 72.28; H 5.89; Cl 12.19; N 9.63.Measured value C 72.03; H 5.94; Cl 12.32; N 9.71.
Embodiment 3: curcuminoids derivative 1,7-two (4-dimethylaminophenyl)-3,5-two (4-bromobenzene imino-)-1,6-heptadiene (DAEBr) synthetic.
The 4-bromaniline that adds 2mmol in there-necked flask; the 5mL anhydrous alcohol solution; then the formic acid and the aluminum trichloride (anhydrous) that add catalytic amount; under stirring; slowly drip the above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 15mL dehydrated alcohol; heating reflux reaction; nitrogen protection; reacted 3 hours, the thin-layer chromatography detection reaction is after reaction finishes; extract organic phase; (sherwood oil: ethyl acetate=4:1), obtain the tawny solid product, productive rate is 34.7% with the silica gel thin-layer chromatography separation.And by FTIR, MALDI-TOP,
1The methods such as HNMR have confirmed the structure of this compound.IR (KBr) ν: 3032,2966,2834,1640,1627,1488-1575,1346,623cm
-1Mass spectrum MALDI-TOF m/z:669 (M+H)
+;
1HNMR (CDCl
3, 400 MHz) and δ: 1.56 (s, 2H ,-CH
2-), 3.07 (s, 12H, N-CH
3), 5.02-6.12 (d, 4H, HC=CH-Ar), 6.45-7.53 (m, 16H, H-Ar).Molecular formula C
35H
34Br
2N
4Ultimate analysis calculated value: C 62.70; H 5.11; Br 23.83; N 8.36.Measured value C 62.43; H 5.18; Br 23.97; N 8.42.
Embodiment 4: curcuminoids derivative 1,7-two (4-dimethylaminophenyl)-3,5-two (4-iodobenzene imino-)-1,6-heptadiene (DAEI) synthetic.
The 4-Iodoaniline that adds 2mmol in there-necked flask; the 5mL anhydrous alcohol solution; then the formic acid and the aluminum trichloride (anhydrous) that add catalytic amount; under stirring; slowly drip the above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 15mL dehydrated alcohol; heating reflux reaction; the thin-layer chromatography detection reaction was reacted in nitrogen protection 7 hours; after reaction finishes; extract organic phase, concentrated, separate (sherwood oil: ethyl acetate=5:1) with silica gel thin-layer chromatography; obtain filbert solid product, productive rate is 31.8%.And by FTIR, MALDI-TOP,
1The methods such as HNMR have confirmed the structure of this compound.IR (KBr) ν: 3029,2962,2831,1637,1625,1485-1572,1343,587cm
-1Mass spectrum MALDI-TOF m/z:765 (M+H)
+;
1HNMR (CDCl
3, 400 MHz) and δ: 1.55 (s, 2H ,-CH
2-), 3.04 (s, 12H, N-CH
3), 5.00-6.11 (d, 4H, HC=CH-Ar), 6.43-7.55 (m, 16H, H-Ar).Molecular formula C
35H
34I
2N
4Ultimate analysis calculated value: C 54.99; H 4.48; I 33.20; N 7.33.Measured value C 54.73; H 4.55; I 33.31; N 7.41.
The present invention embodiment curcuminoids derivative DAEF(embodiment 1), DAECl(embodiment 2), DAEBr(embodiment 3), DAEI(embodiment 4) suppress the growth in vitro activity experiment of streptococcus aureus (bacterium ATCC29213), Streptococcus viridans.
6.1 substratum preparation: extractum carnis 0.3 gram, peptone 1.0 grams, sodium-chlor 0.5 gram, agar 1.5 grams, 100 milliliters, water add 100 milliliters, water in beaker, put into extractum carnis, peptone and sodium-chlor, after heating for dissolving, add agar, stir, supply dehydration after waiting agar to dissolve fully, adjust pH to 7.2～7.6, be divided in each test tube, add cotton plug, use high pressure steam sterilization 30 minutes.
6.2 the separation and purification of bacterium: with aseptic transfering loop difference picking streptococcus aureus and suis culture, first be coated with a mycoderm (account for the dull and stereotyped total area 1/10) at blood agar plate upper end agar surface, with transfering loop after flame sterilization again with " four sections sectional streak methods ": draw altogether 4th district, the bacterium that will mix spreads out.Flat-plate inverted is placed under (37 ± 0.5) ℃ condition subsequently and cultivates 18-24h.
6.3 the purebred amplification of bacterium: with the cooling transfering loop typical bacterial colony of difference picking on the bacterium flat board of above-mentioned cultivation of sterilization, stretch into blood agar slant medium to be inoculated, the line coating of wriggling from bottom to up; The test tube that inoculation is good is put under (37 ± 0.5) ℃ condition cultivates 18-24h.
6.4 the grouping of bacterium: the bacteriostatic experiment of extract adds on plate culture medium for examination bacteria suspension 0.1 ml with 2 kinds of the above-mentioned preparation of aseptic pipette, extract respectively, culture dish is upside down in 37 ℃ of cultivation 24～48 h in incubator, take out the diameter of measuring the filter paper inhibition zone, relatively fungistatic effect.Divide 4 different pharmaceutical groups, do contrast with normal blank, ethyl acetate, curcumine simultaneously, each medicine is done two kinds of bacterial strains experiments, amounts to 14 culture dish.
6.5 testing method
6.5.1 each new synthetic claims that middle 4mg is standby, 40 ℃ of Refrigerator stores of lucifuge.
6.5.2 the preparation of solid medium takes nutrient agar medium and is placed in Erlenmeyer flask, with deionized water, it is fully dissolved, sealing, put into high-pressure sterilizing pot, 121 ℃ of sterilization 15 min to be cooledly take out after 60 ℃, pour in the batch cultur ware, put into refrigerator after to be cooled solidifying, 4 ℃ save backup.
6.5.3 the preparation of bacteria suspension directly get respectively after purebred amplification lawn a little be deployed into 0.5 Maxwell than the bacteria suspension of turbid standard with liquid nutrient medium.And then it is rear standby to carry out dilution in 1: 100 with substratum.Get 3 test tubes, pour respectively equivalent physiological saline into to 1/3 place of test tube, then sterilization 20 min under ultraviolet lamp dip a small amount of 4～5 bacterium colonies of fresh bacterial classification with aseptic cotton carrier and put into physiological saline and fully stir bacterium is uniformly dispersed.Institute all completes on aseptic operating platform in steps.
6.5.4 the bacteriostatic experiment of curcumine and derivative thereof
Be ready to 14 aseptic 5ml EP pipes, carry out respectively mark, golden Portugal bacterium is divided into 7 groups, and numbering I ~ IV number is the medicine group; The curcumine control group; The ethyl acetate control group; Normal blank group, the same streptococcus aureus of suis grouping.The medicine of getting 4mg is dissolved in the ethyl acetate of 20 μ L, is adding the aseptic bacteria culture medium of 2ml, and each group medicine is configured to the liquid storage that concentration is 2mg/ml.The ethyl acetate control group only adds the ethyl acetate of 20 μ L, then adds the 2ml aseptic culture medium.Bacterium colony in solid medium (streptococcus aureus and suis) is taken out respectively the aseptic centrifuge tube of 50ml of putting into the aseptic culture medium that fills 30ml, with pipettor, bacterium liquid is blown and beaten into the single bacteria suspension, to blow and beat afterwards the sucking-off of uniform bacterium liquid and put into ready aseptic 5ml EP pipe, add bacterium liquid 1ml in each EP pipe, after adding bacterium liquid, the medicine that configures is before drawn 1ml and put into golden Portugal bacterium group, 1ml puts into the suis group, the ultimate density that makes medicine is 1mg/ml, fully blows and beats mixing and is placed on 37 ℃ of CO
2Carry out bacterial count after cultivating 24h, 36h in incubator.
6.5.5 bacterial count: the bacterium liquid of 20 μ L is added in the PBS liquid of 3980 μ L, carry out bacterial count after 200 times of dilution bacterium liquid under inverted microscope, the colony number at naked eyes counting tally 4 angles amounts to three times, takes the mean.Calculation formula: total plate count=(four large lattice bacterial count sum/4) * 200 * 10
4
6.5.6 anti-microbial activity standard: according to People's Health Publisher's sixth version " pharmacology " teaching material.The minimum concentration that can suppress bacterial growth in substratum is minimal inhibitory concentration (minimal inhibitory concentration, MIC).To suppress 50% bacterial growth as the curative effect of medication standard.
6.6 fungistatic effect
6.6.1 compare with Normal group:
(1) four new compound has lasting inhibition ability to 24 hours, 36 hours streptococcus aureuses; (2) four new compounds have lasting inhibition ability to 24 hours, 36 hours streptococcus pneumoniaes;
(3) wherein new compound DAEF reaches the most by force 95% to 24 hours streptococcus aureus inhibition abilities;
6.6.2 compare with curcumine:
(1) four new compound suppresses strong (〉 79% of energy force rate curcumine to 24 hours streptococcus pneumoniaes);
(2) four new compounds have lasting inhibition ability to 36 hours streptococcus pneumoniaes, than curcumine strong (〉 72%);
(3) four new compounds suppressed strong (〉 64% of energy force rate curcumine to 36 hours to streptococcus aureus).
Claims (5)
1. curcuminoids contracting aromatic amine Shiff base derivative is characterized in that structural formula is:
Wherein R is one of fluorine, chlorine, bromine, iodine, hydroxyl, methoxyl group, alkyl, and the R base is the neighbour of phenyl ring, to a, position; Have two or more different groups on phenyl ring, the group relative position be connect,, contraposition.
2. the preparation method of a curcuminoids contracting aromatic amine Shiff base derivative, it is characterized in that comprising following steps: with the substituted aromatic amine anhydrous alcohol solution, the formic acid, the aluminum trichloride (anhydrous) that add catalytic amount, stir, drip the curcumin analogue ethanolic soln of above-mentioned reaction preparation, nitrogen protection; Reflux, reactant separates with the method for silica gel column chromatography, namely obtains target product.
3. the preparation method of curcuminoids contracting aromatic amine Shiff base derivative according to claim 2, it is characterized in that step more specifically: be mixed in boron trioxide, methyl ethyl diketone and tributyl borate in three-necked flask and use nitrogen protection, back flow reaction, obtain methyl ethyl diketone and boron trioxide complex compound, then add DMF, 4-dimethylin phenyl aldehyde, n-Butyl Amine 99 reaction, after finishing, adjust pH is 7, the washing organic phase, separate to get the yellow powder product with thin-layer chromatography, be target product; Its reaction process signal formula is as follows:
4. a curcuminoids contracting aromatic amine Shiff base derivative in the application for preparing antibacterials, is characterized in that the curcumine contracting aromatic amine Shiff base derivative that limits with claim 1 prepares antibacterials.
5. curcuminoids contracting aromatic amine Shiff base derivative according to claim 4 in the application of preparation antibacterials, is characterized in that the antibacterials that prepare are used for anti-Staphylococcus aureus, suis.
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| CN110590599A (en) * | 2019-09-30 | 2019-12-20 | 大连民族大学 | Quorum sensing signal molecular structure analogue and preparation method thereof |
| CN111253282A (en) * | 2020-03-31 | 2020-06-09 | 南京解风堂健康管理有限公司 | Curcumin-modified compound for enhancing antibacterial activity and preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590599A (en) * | 2019-09-30 | 2019-12-20 | 大连民族大学 | Quorum sensing signal molecular structure analogue and preparation method thereof |
| CN110590599B (en) * | 2019-09-30 | 2022-07-26 | 大连民族大学 | Quorum sensing signal molecular structure analogue and preparation method thereof |
| CN111253282A (en) * | 2020-03-31 | 2020-06-09 | 南京解风堂健康管理有限公司 | Curcumin-modified compound for enhancing antibacterial activity and preparation method and application thereof |
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