CN103159644B - Curcuminoid condensed aromatic amine Schiff base derivative and application thereof in preparation of antibacterial medicaments - Google Patents
Curcuminoid condensed aromatic amine Schiff base derivative and application thereof in preparation of antibacterial medicaments Download PDFInfo
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- CN103159644B CN103159644B CN201310117849.2A CN201310117849A CN103159644B CN 103159644 B CN103159644 B CN 103159644B CN 201310117849 A CN201310117849 A CN 201310117849A CN 103159644 B CN103159644 B CN 103159644B
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Abstract
The invention relates to a curcuminoid condensed aromatic amine Schiff base derivative and 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 structure formula is shown in the description, wherein R is halogen on benzene ring para-position: fluorine, chlorine, bromine, and iodine. 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 the application in preparation antibacterials thereof, belong to synthesis curcuminoids contracting 3,5-bis-aromatic amine Shiff base derivative with and uses thereof technical field.
Background technology
Turmeric derives from the rhizome of zingiberaceous plant turmeric (Curcumalonga L), within 1842, be therefrom separated to yellow substance turmeric yellow first, curcumine [curcumin, chemical name: 1,7-bis-(4-hydroxy-3-methoxy) phenyl-1,6-heptadiene-3,5-diketone ］ be its principle active component.The chemical structure of curcumine in 1910 is identified first.Research finds, curcumine have anti-oxidant, anti-inflammatory, anti-freezing, lipopenicillinase, atherosclerosis, anti-ageing, eliminate the biological activity such as free radical and Tumor suppression growth.But, due to curcumine poorly water-soluble, especially unstable under neutrality to basic pH conditions, simultaneously after curcumine oral absorption rapidly by liver metabolism, first to cross elimination phenomenon obvious, and bioavailability is low, so carry out suitable structure of modification to curcumine, to improve its bioavailability and drug effect, therefore, structure of modification carried out to curcumine or synthesize the emphasis that curcumin analogue just becomes Chinese scholars research concern.Having wherein to the structural modification of curcumine: (1) is modified two of curcumine carbonyls, synthetic metals title complex etc., such as: publication number is the Chinese patent " application of curcumin-zinc compound in the antibacterial analgesic of preparation or Health Care " of CN101904835A, illustrate that curcumin-zinc compound has good drug effect on analgesia is antibacterial, overcoming ubiquity medicine in the treatment of existing geriatric disease, to be suitable for disease single, the problem that curative effect is desirable not to the utmost; (2) synthesizing the replacement of active methylene group in curcumine structure is also study hotspot, as publication number CN101434525A Chinese patent " 4-(4-hydroxy 3-methoxybenzene methyl) curcumine and the application for the preparation of antitumor drug thereof ", the antitumor drug of synthesis significantly can 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, the phenolic hydroxyl group of curcumine is introduced silane substituted base, painted for silicon materials such as silicon tree elastomericss.
In addition, schiff bases, as the important organic ligand of a class, can form title complex with many metal ions by coordinate bond, therefore be widely used in pharmacy, catalysis, analytical chemistry, corrosion and photochromic field.Within 1931, synthesize schiff bases first by people such as Peiifer, and just really start the attention being subject to 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, the title complex of amino acids, semicarbazone class, contracting amine, heterocyclic, hydrazone class schiff bases and application thereof has antibacterial, sterilization, unique medicinal effect such as antitumor, antiviral.Therefore, how improving bioavailability and drug effect, is one of this area technical problem urgently to be resolved hurrily.
Summary of the invention
The object of the invention is to provide a kind of curcuminoids contracting aromatic amine Shiff base derivative and the application in preparation antibacterials thereof, by synthesis curcumin analogue 1,7-bis-(4-dimethylin) phenyl-1,6-heptadiene-3,5-diketone ］, again in the molecule 3,5-diketone position and bimolecular aromatic amine carry out condensation reaction, form curcuminoids contracting 3,5-bis-aromatic amine Shiff base derivative, and prepare 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 R base is the neighbour of phenyl ring, to a, position; Phenyl ring exists two or more different groups, group relative position be connect, contraposition.
A kind of preparation method of curcuminoids contracting aromatic amine Shiff base derivative, comprise following steps: by substituted aromatic amine anhydrous alcohol solution, add the formic acid of catalytic amount, aluminum trichloride (anhydrous), stir, drip curcumin analogue ethanolic soln prepared by above-mentioned reaction, nitrogen protection; Backflow, the method for reactant silica gel column chromatography is separated, and namely obtains target product.
Step more specifically: boron trioxide, methyl ethyl diketone and tributyl borate are mixed in three-necked flask also with 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 terminating, adjust pH is 7, washing organic phase, is separated to obtain yellow powder product with thin-layer chromatography, is target product; Its reaction process signal formula is as follows:
.
Curcuminoids contracting aromatic amine Shiff base derivative, in an application for preparation antibacterials, prepares 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 synthesis curcumin analogue 1,7-bis-(4-dimethylin) phenyl-1,6-heptadiene-3,5-diketone ］, again in the molecule 3,5-diketone position and bimolecular aromatic amine carry out condensation reaction, form curcuminoids contracting 3,5-bis-aromatic amine Shiff base derivative, and prepare antibacterials, improve 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.
Accompanying drawing explanation
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, by embodiment, the present invention will be further described.
Embodiment 1: the synthesis of curcuminoids derivative 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-fluorobenzene imino-)-1,6-heptadiene (DAEF).
The 4-fluoroaniline of 2mmol is added in there-necked flask; 5mL anhydrous alcohol solution; then formic acid and the aluminum trichloride (anhydrous) of catalytic amount is added; under stirring; the slow dropping above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 12mL dehydrated alcohol; heating reflux reaction; nitrogen protection, reacts 15 hours, thin-layer chromatography detection reaction; after reaction terminates; extract organic phase, concentrated, be separated (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 confirm 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: the synthesis of curcuminoids derivative 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-chlorobenzene imino-)-1,6-heptadiene (DAECl).
The 4-chloroaniline of 2mmol is added in there-necked flask; 5mL anhydrous alcohol solution; then formic acid and the aluminum trichloride (anhydrous) of catalytic amount is added; under stirring; the slow dropping above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 15mL dehydrated alcohol; heating reflux reaction; nitrogen protection, reacts 8 hours, thin-layer chromatography detection reaction; after reaction terminates; extract organic phase, concentrated, be separated (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 confirm 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: the synthesis of curcuminoids derivative 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-bromobenzene imino-)-1,6-heptadiene (DAEBr).
The 4-bromaniline of 2mmol is added in there-necked flask; 5mL anhydrous alcohol solution; then formic acid and the aluminum trichloride (anhydrous) of catalytic amount is added; under stirring; the slow dropping above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 15mL dehydrated alcohol; heating reflux reaction; nitrogen protection; react 3 hours, thin-layer chromatography detection reaction, after reaction terminates; extract organic phase; be separated (sherwood oil: ethyl acetate=4:1) with silica gel thin-layer chromatography, obtain Tan solid product, productive rate is 34.7%.And by FTIR, MALDI-TOP,
1the methods such as HNMR confirm 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: the synthesis of curcuminoids derivative 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-iodobenzene imino-)-1,6-heptadiene (DAEI).
The 4-Iodoaniline of 2mmol is added in there-necked flask; 5mL anhydrous alcohol solution; then formic acid and the aluminum trichloride (anhydrous) of catalytic amount is added; under stirring; the slow dropping above-mentioned product curcumin analogue DAEO of 1mmol and the mixing solutions of 15mL dehydrated alcohol; heating reflux reaction; nitrogen protection, reacts 7 hours, thin-layer chromatography detection reaction; after reaction terminates; extract organic phase, concentrated, be separated (sherwood oil: ethyl acetate=5:1) with silica gel thin-layer chromatography; obtain hazel-color solid product, productive rate is 31.8%.And by FTIR, MALDI-TOP,
1the methods such as HNMR confirm 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's embodiment curcuminoids derivative DAEF(embodiment 1), DAECl(embodiment 2), DAEBr(embodiment 3), DAEI(embodiment 4) suppress streptococcus aureus (bacterium ATCC29213), Streptococcus viridans growth in vitro activity experiment.
6.1 medium preparing: extractum carnis 0.3 gram, peptone 1.0 grams, 0.5 gram, sodium-chlor, 1.5 grams, agar, 100 milliliters, water adds water 100 milliliters in beaker, puts into extractum carnis, peptone and sodium-chlor, after heating for dissolving, add agar, stir, after waiting agar to dissolve completely, supply dehydration, adjust pH is to 7.2 ~ 7.6, be divided in each test tube, add cotton plug, with high pressure steam sterilization 30 minutes.
The separation and purification of 6.2 bacteriums: with aseptic transfering loop picking streptococcus aureus and streptococcus culture respectively, first be coated with a mycoderm (accounting for 1/10 of the dull and stereotyped total area) at blood agar plate upper end agar surface, by transfering loop after flame sterilization again with " four sections of streaking inoculation ": Gong Hua 4 district, spreads out the bacterium mixed.18-24h is cultivated under subsequently flat-plate inverted being placed in (37 ± 0.5) DEG C condition.
The purebred amplification of 6.3 bacteriums: the transfering loop cooled with sterilizing is the typical bacterial colony of difference picking on the Bacterial Plate of above-mentioned cultivation, stretches into blood agar slant medium to be seeded, line coating of wriggling from bottom to up; 18-24h is cultivated under the test tube inoculated being put in (37 ± 0.5) DEG C condition.
The grouping of 6.4 bacteriums: the bacteriostatic experiment of extract adds on plate culture medium with 2 kinds of confession examination bacteria suspension 0.1 ml that Sterile pipette draws above-mentioned preparation respectively, culture dish is upside down in 37 DEG C of cultivation 24 ~ 48 h in incubator, take out the diameter measuring filter paper inhibition zone, compare fungistatic effect.Divide 4 different pharmaceutical groups, contrast simultaneously with normal blank, ethyl acetate, curcumine, each medicine does two kinds of bacterial strains experiments, amounts to 14 culture dish.
6.5 testing method
6.5.1 each new synthetic claims middle 4mg for subsequent use, lucifuge 40 DEG C of Refrigerator stores.
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 DEG C of sterilizing 15 min, to be cooledly take out to after 60 DEG C, pour in batch cultur ware, to be cooled solidify after put into refrigerator, 4 DEG C save backup.
6.5.3 the lawn after the preparation of bacteria suspension directly gets purebred amplification is respectively deployed into the bacteria suspension of 0.5 Maxwell than turbid standard with liquid nutrient medium a little.And then it is for subsequent use after carrying out 1: 100 dilution with substratum.Get 3 test tubes, pour 1/3 place of normal saline to test tube respectively into, sterilizing 20 min under ultraviolet lamp, then 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 in steps on aseptic operating platform.
6.5.4 the bacteriostatic experiment of curcumine and derivative thereof
Get out 14 aseptic 5ml EP manage, carry out mark respectively, S. aureus L-forms is divided into 7 groups, and No. I ~ IV, numbering is medicine group; Curcumine control group; Ethyl acetate control group; Normal blank control group, suis divides into groups same streptococcus aureus.The medicine getting 4mg is dissolved in the ethyl acetate of 20 μ L, is adding the aseptic bacteria culture medium of 2ml, is become by each group of medicine ordinance concentration to be the liquid storage of 2mg/ml.Ethyl acetate control group only adds the ethyl acetate of 20 μ L, then adds 2ml aseptic culture medium.Bacterium colony (streptococcus aureus and suis) in solid medium is taken out the 50ml sterile centrifugation tube putting into the aseptic culture medium filling 30ml respectively, with pipettor, bacterium liquid is blown and beaten into single bacteria suspension, the sucking-off of uniform for piping and druming bacterium liquid is put into ready aseptic 5ml EP pipe afterwards, bacterium liquid 1ml is added in each EP pipe, after adding bacterium liquid, the medicament extraction 1ml configured before is put into S. aureus L-forms group, 1ml puts into suis group, make the ultimate density of medicine be 1mg/ml, fully piping and druming mixing is placed on 37 DEG C of CO
2bacterial count is carried out after cultivating 24h, 36h in incubator.
6.5.5 bacterial count: added by the bacterium liquid of 20 μ L in the PBS liquid of 3980 μ L, carry out bacterial count after dilution bacterium liquid 200 times 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 of bacterial growth in substratum can be suppressed to be minimal inhibitory concentration (minimal inhibitory concentration, MIC).To suppress 50% bacterial growth for curative effect of medication standard.
6.6 fungistatic effect
6.6.1 compare with Normal group:
(1) four new compound has lasting rejection ability to 24 hours, 36 hours streptococcus aureuses; (2) four new compounds have lasting rejection ability to 24 hours, 36 hours streptococcus pneumoniaes;
(3) wherein new compound DAEF reaches the most by force 95% to 24 hours streptococcus aureus rejection ability;
6.6.2 compare with curcumine:
(1) four new compound was to 24 hours streptococcus pneumoniae rejection ability stronger than curcumine (>79%);
(2) four new compounds have lasting rejection ability to 36 hours streptococcus pneumoniaes, stronger than curcumine (>72%);
(3) four new compounds to 36 hours to streptococcus aureus rejection ability stronger than curcumine (>64%).
Claims (3)
1. a curcuminoids contracting aromatic amine Shiff base derivative, is characterized in that structural formula is:
Wherein R is the halogen in phenyl ring contraposition: fluorine, chlorine, bromine, iodine;
Halogen in phenyl ring contraposition is fluorine, and compound is: 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-fluorobenzene imino-)-1,6-heptadiene);
Halogen in phenyl ring contraposition is chlorine, and compound is: 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-chlorobenzene imino-)-1,6-heptadiene);
Halogen in phenyl ring contraposition is bromine, and compound is: 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-bromobenzene imino-)-1,6-heptadiene);
Halogen in phenyl ring contraposition is iodine, and compound is: 1,7-bis-(4-dimethylaminophenyl)-3,5-bis-(4-iodobenzene imino-)-1,6-heptadiene).
2. curcuminoids contracting aromatic amine Shiff base derivative is in an application for preparation antibacterials, it is characterized in that the curcumine contracting aromatic amine Shiff base derivative limited by claim 1 prepares antibacterials.
3. curcuminoids contracting aromatic amine Shiff base derivative according to claim 2 is in the application of preparation antibacterials, it is characterized in that the antibacterials prepared are for anti-Staphylococcus aureus, suis.
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| 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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| CN102134197A (en) * | 2010-12-29 | 2011-07-27 | 浙江工业大学 | Green synthesis method for schiff base compounds |
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| CN1646473A (en) * | 2002-04-17 | 2005-07-27 | 北卡罗来纳查佩尔山大学 | Novel curcumin analogues and uses thereof |
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