CN104311546A - Calixarene-rare earth complex and its preparation method and use - Google Patents
Calixarene-rare earth complex and its preparation method and use Download PDFInfo
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- CN104311546A CN104311546A CN201410465467.3A CN201410465467A CN104311546A CN 104311546 A CN104311546 A CN 104311546A CN 201410465467 A CN201410465467 A CN 201410465467A CN 104311546 A CN104311546 A CN 104311546A
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- calixarene
- rare earth
- thiadiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a novel calixarene-rare earth complex which has antibacterial activity and contains triazole and thiadiazole and its preparation method and use, and belongs to the technical field of antibacterial materials and a preparation method thereof. The preparation method comprises that under the action of K2CO3 and acetone, tert-butylcalix[4]arene and [(1H-1,2,4-triazole-1-yl)]-1,3,4-thiadiazole-2-thiol undergo a reaction to produce an intermediate I, under the action of K2CO3 and acetone, the intermediate I and ethyl 2-bromoacetate undergo a reaction to produce a calixarene II containing triazole and thiadiazole, and the calixarene II and LaCl3.6H2O undergo a reaction in a mixed solution of trichloromethane, acetonitrile and ethanol to produce the calixarene-rare earth complex which has antibacterial activity and contains triazole and thiadiazole. The calixarene-rare earth complex which has antibacterial activity and contains triazole and thiadiazole has strong effects of inhibiting escherichia coli (ATCC25922) and staphylococcus aureus (ATCC29213) and has a good application prospect.
Description
Technical field
The invention belongs to anti-biotic material and preparation method thereof technical field, be specifically related to a kind of calixarene rare earth compounding containing triazole and thiadiazoles with anti-microbial activity, and be applied to escherichia coli (ATCC25922) and streptococcus aureus (ATCC 29213) on suppression cotton fabric.
Background technology
Because calixarene has unique three-dimensional lumen structure, its cavity size can regulate with the change of Component units number, and has induction adaptation ability good especially.Meanwhile, calixarene also has that fusing point is high, thermostability and chemical stability good, and unique physics, the chemical property such as solubleness is low in most of solvent, toxicity is low, mixing property is good.Such as Sulfonated calixarenes is a kind of potential pharmaceutical carrier, not only has good inclusion characteristic, and has low toxicity, antithrombotic and the characteristic such as antiviral.Therefore calixarene and derivative very wide in biopharmaceutics field application prospect; Rare earth compound and rare earth organic complex have the effects such as anti-inflammatory, antibacterial, deodorization, the exploitation being developed as antibacterial deodourizing trevira of the inorganic rare earth antibacterial deodourizing medicament that such as bacterium zeolite (zeolite is carrier) is representative is laid a good foundation, and antibacterial deodourizing trevira is developed rapidly.For these reasons, we have invented a kind of calixarene rare earth compounding containing triazole and thiadiazoles with anti-microbial activity, to escherichia coli on cotton fabric and streptococcus aureus being had to stronger bacteriostasis.
Summary of the invention
The object of the invention is to cup [4] aromatic hydrocarbons and triazole and thiadiazoles construct in same a part, then generate the new calixarene rare earth compounding containing triazole and thiadiazoles with anti-microbial activity with rare earth compound complexing.
The object of the present invention is achieved like this: a kind of calixarene rare earth compounding intermediate II, and containing triazole and thiadiazoles, chemical structural formula is as follows:
The calixarene intermediate II of this triazole and thiadiazoles and LaC1
36H
2o, to wait amount of substance than mixing, forms the calixarene rare earth compounding containing triazole and thiadiazoles in the mixing solutions of trichloromethane, second eyeball and ethanol.
A kind of preparation method of calixarene rare earth compounding is as follows:
A: by 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons and [(1H-1,2,4-triazol-1-yl)]-1,3,4-thiadiazoles-2-mercaptan, joins in the reactor that tetrahydrofuran (THF) (THF), NaOH are housed, N
2protection lower backflow 38-50 hour, after backflow terminates, rotary evaporation, except desolventizing, adds CH in resistates
2cl
2, washing organic phase, and use anhydrous Na
2sO
4drying, filters, and rotary evaporation is except desolventizing again, and obtain crude product, crude product ethyl acetate-light petrol recrystallization obtains intermediate compound I;
B: by the intermediate I, 2-ethyl bromoacetate, the K that obtain in steps A
2cO
3, organic solvent joins in reactor in the lump, it is complete that TLC detects raw material primitive reaction; Pressure reducing and steaming solvent, adds chloroform, washing organic phase, and uses anhydrous Na
2sO
4drying, filters, and rotary evaporation, except desolventizing, obtains crude product, and crude product trichloromethane-sherwood oil recrystallization obtains the calixarene intermediate II containing triazole and thiadiazoles;
C: by obtained by intermediate II, LaC1 in step C
36H
2o is dissolved in the mixing solutions of trichloromethane, second eyeball and ethanol, stirring makes it all dissolve, obtain mixing solutions, this mixing solutions is stirred 8-10 hour at normal temperatures, and underpressure distillation, except desolventizing, obtains solid, gained solid trichloromethane is dissolved, the a small amount of water repetitive scrubbing of organic phase, drying, filtration, remove trichloromethane under reduced pressure, obtains white shape solid target compound with ethyl acetate-light petrol recrystallization.
Described 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons, [(1H-1,2,4-triazol-1-yl)]-1,3,4-thiadiazoles-2-mercaptan, NaOH amount of substance than for 1:2-6:2-8; The weight of THF is 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons, [(1H-1,2,4-triazol-1-yl)]-1, the 28-35 of 3,4-thiadiazoles-2-mercaptan, NaOH gross weight doubly, CH
2cl
2weight be 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons, [(1H-1,2,4-triazol-1-yl)]-1,3,4-thiadiazoles-2-mercaptan, NaOH gross weight 20-30 doubly.
Described intermediate I, 2-ethyl bromoacetate, K
2cO
3the ratio of amount of substance be 1:0.5-7:2-8, the weight of organic solvent is intermediate I, 2-ethyl bromoacetate, K
2cO
3the 18-30 of gross weight doubly.
Described intermediate II, LaC1
36H
2the ratio of the amount of substance of O is 1:1; The weight of the mixing solutions of trichloromethane, second eyeball and ethanol is intermediate II, LaC1
36H
2doubly, wherein the volume ratio of trichloromethane, second eyeball and ethanol is 1:1:1 to the 35-45 of O gross weight.
In described steps A, the volume ratio of ethyl acetate and sherwood oil is 2:l; In step B, the volume ratio of ethyl acetate and sherwood oil is 3:1; In step C, the volume ratio of ethyl acetate and sherwood oil is 1:1.
Organic solvent described in described step B is any one in tetrahydrofuran (THF), DMF, methyl-sulphoxide.
Above-mentioned calixarene rare earth compounding is applied to and suppresses on cotton fabric on escherichia coli (ATCC25922) and streptococcus aureus (ATCC 29213).
Technical scheme of the present invention has following beneficial effect:
(1) the calixarene rare earth compounding fungistat containing triazole and thiadiazoles provided by the invention, simple to operate, and technique is advanced, solvent recoverable;
(2) fire retardant provided by the invention is incorporated in triazole and thiadiazoles by cup [4] aromatic ring structure structural unit, to the escherichia coli (ATCC25922) on cotton fabric and the stronger fungistatic effect of streptococcus aureus (ATCC 29213).
(3) raw material used in the present invention is easy to get, technique is advanced, be easy to suitability for industrialized production.
Embodiment
Embodiment 1
Below in conjunction with embodiment, the invention will be further described, but the scope of protection of present invention is not limited to the scope of embodiment statement.
A preparation method for calixarene rare earth compounding, step is:
Take [(1H-1,2,4-triazol-1-yl)]-1,3,4-thiadiazoles-2-mercaptan (8mmol, 1.464g), NaOH (8mmol, 0.32g), 120mL THF in round-bottomed flask, heated and stirred 1.0 hours, then add 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons (2mmol, 1.72g), N
2the lower backflow of protection 45 hours, after backflow terminates, rotary evaporation, except desolventizing, adds CH in resistates
2cl
2100mL, washing organic phase, and use anhydrous Na
2sO
4drying, filters, and rotary evaporation is except desolventizing, and obtain crude product, crude product ethyl acetate-light petrol recrystallization (V ethyl acetate: V sherwood oil=2:l) obtains intermediate compound I, yield 85.2%;
Intermediate compound I 2.12g (2mmol), 2-ethyl bromoacetate 1.99g (2mmol), K
2cO
31.66g (12mmol), DMF (DMF) 150mL are placed in flask, back flow reaction 24h.Pressure reducing and steaming solvent, adds a small amount of chloroform, washing organic phase, and uses anhydrous Na
2sO
4drying, filters, and rotary evaporation, except desolventizing, obtains crude product, and crude product trichloromethane-sherwood oil recrystallization (V ethyl acetate: V sherwood oil=3:l) obtains the calixarene intermediate II containing triazole and thiadiazoles, yield 80.5%;
By calixarene, 1.232g (0.1mmol) LaC1 of 1.24g (0.1mmol) containing triazole and thiadiazoles
36H
20 calixarene containing triazole and thiadiazoles is dissolved in 100mL trichloromethane, acetonitrile and ethanol (V
trichloromethane: V
acetonitrile: V
ethanol=1:1:1) mixing solutions in, stir make it all dissolve.Mixing solutions stirs 8-10 hour at normal temperatures, remove solvent under reduced pressure, gained solid trichloromethane dissolves, a small amount of water repetitive scrubbing of organic phase, drying, filtration, remove trichloromethane under reduced pressure, obtain white shape solid target compound with ethyl acetate-light petrol recrystallization.
The compound outward appearance that the present invention obtains is white solid, and this compound can be dissolved in methyl-sulphoxide, DMF equal solvent.
The analytical results of a kind of calixarene rare earth compounding containing triazole and thiadiazoles that the present invention obtains is as follows:
Its outward appearance of compound is white solid, results of IR: FT-IR (KBr), be O-H stretching vibration peak near v/cm-1:3310, be phenyl ring and triazole ring C-H stretching vibration peak near 3030, near 1740 be C=O stretching vibration peak 1465,1600 neighbouring be C=N and C=C stretching vibration peak; Proton nmr spectra analytical results:
1h NMR (DMSO-d
6, 400MHz): 8.14 (s, 2H, 2CH), 8.02 (s, 2H, 2CH), 6.79 (s, 8H, Ar-H), 4.99 (s, 4H, 2CH
2), 4.90 (s, 4H, 2ArOCH
2), 4.34 (t, 4H, 2ArOCH
2), 3.81 (s, 8H, 4ArCH
2ar), 3.35 (t, 4H, 2CH
2), 1.34 (s, 36H, 4C (CH
3)
3, 1.30 (t, 6H, 2CH
3).
Embodiment 2:
By [(1H-1,2,4-triazol-1-yls)]-1,3,4-thiadiazoles-2-mercaptan be decreased to 1.10g (6mmol), other is with example one, the yield 80.3% of obtained intermediate I.
Embodiment 3:
By [(1H-1,2,4-triazol-1-yls)]-1,3,4-thiadiazoles-2-mercaptan be increased to 1.83g (10mmol), other is with example one, the yield 85.8% of obtained intermediate I.
Embodiment 4:
Solvent changes methyl-sulphoxide into, and other is with example one, and it contains the calixarene intermediate II yield 78.3% of triazole and thiadiazoles.
Embodiment 5:
Solvent changes tetrahydrofuran (THF) into, and other is with example one, and it contains the calixarene intermediate II yield 75.1% of triazole and thiadiazoles.
Calixarene rare earth compounding containing triazole and thiadiazoles provided by the invention has stronger bacteriostasis to escherichia coli on cotton fabric (ATCC25922) and streptococcus aureus (ATCC 29213), applies as follows:
Anti-bacteria cloth after arrangement adopts K-B inhibition zone method to measure title complex to the anti-microbial property of escherichia coli (ATCe25922), streptococcus aureus (ATCC29213).Be by force antibacterial (s) as antibacterial circle diameter=20mm, be medium tenacity antibacterial (MS) when antibacterial circle diameter is between 10-20mm, be weak antibacterial (W) when antibacterial circle diameter is between 6-10mm, without being not antibacterial (O) time antibacterial, anti-bacteria test result is as shown in table 1 below.
Table 1 title complex of the present invention compares with penicillin G antibiotic tsiklomitsin antibacterial ability
Claims (8)
1. a calixarene rare earth compounding, is characterized in that, chemical structural formula is as follows:
Containing triazole and thiadiazoles in this calixarene title complex.
2. a preparation method for calixarene rare earth compounding, is characterized in that, comprises the following steps:
A: by 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons and [(1H-1,2,4-triazol-1-yl)]-1,3,4-thiadiazoles-2-mercaptan, joins in the reactor that tetrahydrofuran (THF) (THF), NaOH are housed, N
2protection lower backflow 38-50 hour, after backflow terminates, rotary evaporation, except desolventizing, adds CH in resistates
2cl
2, washing organic phase, and use anhydrous Na
2sO
4drying, filters, and rotary evaporation is except desolventizing again, and obtain crude product, crude product ethyl acetate-light petrol recrystallization obtains intermediate compound I;
B: by the intermediate I, 2-ethyl bromoacetate, the K that obtain in steps A
2cO
3, organic solvent joins in reactor in the lump, it is complete that TLC detects raw material primitive reaction; Pressure reducing and steaming solvent, adds chloroform, washing organic phase, and uses anhydrous Na
2sO
4drying, filters, and rotary evaporation, except desolventizing, obtains crude product, and crude product trichloromethane-sherwood oil recrystallization obtains the calixarene intermediate II containing triazole and thiadiazoles;
C: by obtained by intermediate II, LaC1 in step C
36H
2o is dissolved in the mixing solutions of trichloromethane, second eyeball and ethanol, stirring makes it all dissolve, obtain mixing solutions, this mixing solutions is stirred 8-10 hour at normal temperatures, and underpressure distillation, except desolventizing, obtains solid, gained solid trichloromethane is dissolved, the a small amount of water repetitive scrubbing of organic phase, drying, filtration, remove trichloromethane under reduced pressure, obtains white shape solid target compound with ethyl acetate-light petrol recrystallization.
3. the preparation method of calixarene rare earth compounding according to claim 2, it is characterized in that: 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons, [(1H-1,2,4-triazol-1-yl)]-1, the amount of substance of 3,4-thiadiazoles-2-mercaptan, NaOH is than being 1:2-6:2-8; The weight of THF is 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons, [(1H-1,2,4-triazol-1-yl)]-1, the 28-35 of 3,4-thiadiazoles-2-mercaptan, NaOH gross weight doubly, CH
2cl
2weight be 25,27-bis-(2-bromine oxethyl)-26,28-dihydroxyl-5,11,17,23-tetra-tert cup [4] aromatic hydrocarbons, [(1H-1,2,4-triazol-1-yl)]-1,3,4-thiadiazoles-2-mercaptan, NaOH gross weight 20-30 doubly.
4. the preparation method of calixarene rare earth compounding according to claim 2, is characterized in that: intermediate I, 2-ethyl bromoacetate, K
2cO
3the ratio of amount of substance be 1:0.5-7:2-8, the weight of organic solvent is intermediate I, 2-ethyl bromoacetate, K
2cO
3the 18-30 of gross weight doubly.
5. the preparation method of calixarene rare earth compounding according to claim 2, is characterized in that: intermediate II, LaC1
36H
2the ratio of the amount of substance of O is 1:1; The weight of the mixing solutions of trichloromethane, second eyeball and ethanol is intermediate II, LaC1
36H
2doubly, wherein the volume ratio of trichloromethane, second eyeball and ethanol is 1:1:1 to the 35-45 of O gross weight.
6. the preparation method of calixarene rare earth compounding according to claim 2, is characterized in that: in steps A, the volume ratio of ethyl acetate and sherwood oil is 2:l; In step B, the volume ratio of ethyl acetate and sherwood oil is 3:1; In step C, the volume ratio of ethyl acetate and sherwood oil is 1:1.
7. the preparation method of calixarene rare earth compounding according to claim 2, is characterized in that: organic solvent described in step B is any one in tetrahydrofuran (THF), DMF, methyl-sulphoxide.
8. suppressing the application on cotton fabric on escherichia coli (ATCC25922) and streptococcus aureus (ATCC 29213) according to any one calixarene rare earth compounding in right 1-7.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105884710A (en) * | 2016-06-08 | 2016-08-24 | 南开大学 | 1,3,4-oxadiazole Cu2+ fluorescent probe based on calixarene and synthetic method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105884710A (en) * | 2016-06-08 | 2016-08-24 | 南开大学 | 1,3,4-oxadiazole Cu2+ fluorescent probe based on calixarene and synthetic method thereof |
| CN105884710B (en) * | 2016-06-08 | 2021-07-02 | 南开大学 | 1,3, 4-oxadiazole Cu based on calixarene2+Fluorescent probe and synthetic method thereof |
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Application publication date: 20150128 |