CN105878236B - To application of the N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of anti-Staphylococcus aureus - Google Patents
To application of the N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of anti-Staphylococcus aureus Download PDFInfo
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- CN105878236B CN105878236B CN201610243365.6A CN201610243365A CN105878236B CN 105878236 B CN105878236 B CN 105878236B CN 201610243365 A CN201610243365 A CN 201610243365A CN 105878236 B CN105878236 B CN 105878236B
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- Prior art keywords
- aminotoluene
- schiff bases
- staphylococcus aureus
- ortho
- benzaldehyde contracting
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
Abstract
The invention discloses the applications to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of anti-Staphylococcus aureus.The structural formula such as following formula to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases（I）It is shown：.The compound has a good antibacterial activity, and nearly to the inhibiting rate of staphylococcus aureus 100%, and the preparation method of the compound is simple, at low cost, is highly suitable for mass producing.Therefore, preparation method of the invention and its antimicrobial compound that is prepared, in particular for staphylococcus aureus, have good application prospect to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of antibacterial and prepare inhibiting-bacteria preparation.
Description
Technical field
The invention belongs to compound technicals.Exist more particularly, to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases
Application in terms of anti-Staphylococcus aureus.
Background technology
Schiff bases is primarily referred to as containing imines or azomethine characteristic group（-RC=N-）A kind of organic compound, it is usually uncommon
Husband's alkali is condensed by amine and active carbonyl group.
Schiff bases compound and its metal complex are in medicine, catalysis, analytical chemistry, corrosion and photochromic field
Important application.In medical domain, schiff bases has antibacterial, sterilization, antitumor, antiviral bioactivity；In catalytic field,
The cobalt and nickel complex of schiff bases have been used as catalyst to use；In analysis field, schiff bases is as good ligand, Ke Yiyong
Differentiate, identifies the content of metal ion and quantitative analysis metal ion；In corrosion field, certain aromatic schiff bases are frequent
Corrosion inhibiter as copper；In photochromic field, certain schiff bases containing characteristic group also have unique application.Therefore,
There are the largely study on the synthesis about Schiff bases compound and property research.
Invention content
The object of the present invention is to provide a kind of new Schiff bases compounds, i.e., uncommon to N imidazoles benzaldehyde contracting ortho-aminotoluenes
Husband's alkali, the application in terms of anti-Staphylococcus aureus.
Another object of the present invention is to provide the above-mentioned preparation method to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases.
Above-mentioned purpose of the present invention is achieved through the following technical solutions：
The invention discloses to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases answering in terms of anti-Staphylococcus aureus
With.
The structural formula such as following formula to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases（I）It is shown：
。
It is above-mentioned to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases answering in terms of the preparation for preparing anti-Staphylococcus aureus
With also within protection scope of the present invention.
In addition, the above-mentioned preparation method to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases is：
In absolute ethyl alcohol, N imidazolyl benzaldehydes and ortho-aminotoluene will be mixed, stirring, be placed 20~35 days under room temperature
Afterwards, faint yellow bulk crystals are precipitated.
Preferably, above-mentioned preparation method is：N imidazolyl benzaldehydes and ortho-aminotoluene will be dissolved in absolute ethyl alcohol respectively,
Two parts of solution are mixed again, stirring, after being placed 20~35 days under room temperature, there are faint yellow bulk crystals to be precipitated；Wherein, described to N
The ratio between amount of substance of imidazolyl benzaldehyde and ortho-aminotoluene is 1：1~2（The two heats after mixing in ethanol, then cannot get
The product）.
It is further preferred that after there are faint yellow bulk crystals to be precipitated, dried on filter paper after being then sucked out with rubber head dropper.
Preparation method of the present invention obtains the yield of product 96% or more.
Wherein it is preferred to which the room temperature refers to 15~25 DEG C.
Preferably, the amount ratio of the substance to N imidazolyl benzaldehydes and ortho-aminotoluene is 1：1.
Preferably, it is placed 15~40 days under the room temperature.
It is highly preferred that being placed 20~35 days under the room temperature.
It is highly preferred that being placed 25~30 days under the room temperature.
Most preferably, it is placed 28 days under the room temperature.
The invention has the advantages that：
The present invention provides a kind of new antimicrobial compounds to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases, the compound
With good antibacterial activity, nearly to the inhibiting rate of staphylococcus aureus 100%.
Moreover, the preparation method of the compound is simple, at low cost, it is highly suitable for mass producing.Therefore, of the invention
Preparation method and its antimicrobial compound that is prepared are to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases antibacterial and prepare antibacterial
There is good application prospect in terms of preparation.
Description of the drawings
Fig. 1 is the mono-crystalline structures to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases.
Fig. 2 is the nuclear magnetic spectrum to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases（It is whole）.
Fig. 3 is the nuclear magnetic spectrum to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases（Part）.
Fig. 4 is to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases to the inhibiting effect of staphylococcus aureus.
Specific implementation mode
It is further illustrated the present invention below in conjunction with Figure of description and specific embodiment, but embodiment is not to the present invention
It limits in any form.Unless stated otherwise, the present invention uses reagent, method and apparatus routinely try for the art
Agent, method and apparatus.
Unless stated otherwise, following embodiment agents useful for same and material are purchased in market.
Preparation of the embodiment 1 to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases
It 1, respectively will be to N imidazolyl benzaldehydes and ortho-aminotoluene according to 1：The amount of 1 substance than being dissolved in anhydrous second respectively
In alcohol, two parts of solution are mixed, stirring, after being placed 28 days under room temperature, there are faint yellow bulk crystals to be precipitated（The two is mixed in ethanol
It is heated after conjunction, then cannot get the product）, yield is 96% or more.Then it is dried on filter paper after being sucked out with rubber head dropper.
Wherein, the room temperature refers to 15~25 DEG C.
2, the above-mentioned product being prepared is identified.The structural formula of the compound such as following formula（I）It is shown：
。
The mono-crystalline structures of the compound are as shown in Fig. 1.
Crystal parameter is respectively：P2 (1)/n crystallographic systems, a=13.0657, b=8.2103, c=14.0414；α=90.000, β=
111.788 γ=90.000；r=0.0437.
The nuclear magnetic spectrum of the compound is as shown in Fig. 2 and 3.
Fig. 2 is its HNMR spectrogram（It is whole）, Fig. 3 is its Local map.It is-CH in molecular structure at δ 2.413（Hydrogen）It is unimodal,
At 8.435 in-CH=N- 1 hydrogen atom it is unimodal, 7.0-8.2 at, 11 hydrogen atom peaks are shared, for two phenyl ring and 1 miaow
Corresponding 11 hydrogen atoms in azoles ring.
Antibacterial activity in vitro research of the embodiment 2 to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases
1, product prepared by embodiment（Crystal）It is first cleaned with ethyl alcohol, dries grind into powder and pour into sample cell, use CH2Cl2
Dissolving, then the scraps of paper to have sterilized are put into sample cell（Circle, diameter 0.5cm）Adsorption sample solution, by the scraps of paper of carry sample
Taking-up is dried, and is put into the agar medium of staphylococcus aureus, is cultivated 24 hours at 5 groups, 37 DEG C of Duplicate Samples, rear observation suppression
Bacterium circle.
In addition, the scraps of paper are put into absolute ethyl alcohol, CH is placed into after drying2Cl2In, taking-up is dried as blank control, does 5
Group blank control.
2, result is as shown in Fig. 4, and apparent inhibition zone occurs in experimental group, and blank control does not find inhibition zone, table
Bright provided by the invention have apparent bacteriostatic activity to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases to staphylococcus aureus.
In addition, larger to the inhibition zone of staphylococcus aureus to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases hand over obviously,
And the not growth of bacterium completely in inhibition zone, the compound nearly to the inhibiting rate of staphylococcus aureus 100%.
Claims (2)
1. pair application of the N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of the preparation for preparing anti-Staphylococcus aureus,
It is characterized in that, the structural formula such as following formula to N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases（I）It is shown：
。
2. a kind of antiseptic of anti-Staphylococcus aureus, which is characterized in that containing described in claim 1 to N imidazoles benzene first
Aldehyde contracting ortho-aminotoluene schiff bases.
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| CN201610243365.6A CN105878236B (en) | 2016-04-19 | 2016-04-19 | To application of the N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of anti-Staphylococcus aureus |
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| CN201610243365.6A CN105878236B (en) | 2016-04-19 | 2016-04-19 | To application of the N imidazoles benzaldehyde contracting ortho-aminotoluene schiff bases in terms of anti-Staphylococcus aureus |
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| CN105878236B true CN105878236B (en) | 2018-10-26 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5656624A (en) * | 1994-12-21 | 1997-08-12 | Schering Corporation | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents |
| CN103156844A (en) * | 2011-12-15 | 2013-06-19 | 天津市国际生物医药联合研究院 | Application of Schiff base compound in inhibition of activity of NDM-1 |
-
2016
- 2016-04-19 CN CN201610243365.6A patent/CN105878236B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5656624A (en) * | 1994-12-21 | 1997-08-12 | Schering Corporation | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents |
| CN103156844A (en) * | 2011-12-15 | 2013-06-19 | 天津市国际生物医药联合研究院 | Application of Schiff base compound in inhibition of activity of NDM-1 |
Non-Patent Citations (2)
| Title |
|---|
| Synthesis and antimicrobial evaluation of novel N-(4-(pyrrolidin-1-yl)benzylidene)-arylamine and diethyl(arylamino)(4-(pyrrolidin-1-yl)phenyl)methyl phosphonate;Sandeep D. Pardeshi, et al.;《Heterocyclic Letters》;20151231;第5卷(第1期);第97-104页，尤其是第101页表1和103页表4 * |
| 新型抗菌药物咪唑类化合物研究;袁勇等;《第四届全国化学生物学学术会议暨国际化学与生物/医学交叉研讨会》;20051031;第201页，尤其是第201页第1段第3-4行 * |
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