CN102757405A - Vanilline derivative containing thiadiazole, preparation method and purpose thereof - Google Patents
Vanilline derivative containing thiadiazole, preparation method and purpose thereof Download PDFInfo
- Publication number
- CN102757405A CN102757405A CN2012102588983A CN201210258898A CN102757405A CN 102757405 A CN102757405 A CN 102757405A CN 2012102588983 A CN2012102588983 A CN 2012102588983A CN 201210258898 A CN201210258898 A CN 201210258898A CN 102757405 A CN102757405 A CN 102757405A
- Authority
- CN
- China
- Prior art keywords
- organic solvent
- mesh
- food grade
- obtains
- vanillin food
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to a vanilline derivative containing thiadiazole, a preparation method and a purpose thereof. The derivative has the structural formula as follows: in the structural formula, (1) R1 is the same as R2, R1 and R2 are H, and R3 is NO2; (2), R1 is the same as R2, R1 and R2 are H, and R3 is Br; (3), R1 is the same as R3, R1 and R3 are H, and R2 is NO2; (4), R2 is the same as R3, and R1 is Br; (5), R1 is the same as R3, R1 and R2 are H, and R2 is Br; (6), R1 is Br, R2 is H, and R3 is NO2; (7), R1 is the same as R3, R1 and R3 are H, and R2 is OCH3; (8) R1 is the same as R2, R1 and R2 are H, and R3 is OCH3; or (9), R2 is the same as R3, R2 and R3 are H, and R1 is NO2. The preparation method comprises the following steps: at first, substituted vanilline, hydrazine hydrate and phenyl iso-thiocyanate react, and then a catalyst is added to react to obtain vanilline derivative containing thiadiazole. The vanilline derivative containing thiadiazole has a remarkable inhibition effect, and can be used for preparing antibacterials; and the preparation method of the vanilline derivative is simple and feasible, and is easy to implement.
Description
Technical field
The present invention relates to the vanillin food grade,1000.000000ine mesh verivate, be specifically related to one type of vanillin food grade,1000.000000ine mesh verivate, Its Preparation Method And Use that contains thiadiazoles.
Background technology
In decades in the past, the problem of multidrug resistance mikrobe has reached thrilling degree in the whole world.Therefore, seek efficient, as to hang down the anti-microbial infection of spinoff novel drugs and become an important and urgent task.
Thiadiazoles is to produce Kefzol, cefcanel, cefazedone, Cephanone, cefaparole, cynnematin BL-S339; The important intermediate of medicine such as BRL-16933; Because it is little that such medicine has an antibiotic wide spectrum, good absorption, spinoff; Be particularly suited for characteristics such as oral absorption, therefore be widely used clinically.It is reported that vanillin food grade,1000.000000ine mesh also has certain antimicrobial antiphlogistic activity.Therefore, the present invention will contain various substituent vanillin food grade,1000.000000ine meshs and introduce 1,3, the 4-thiadiazoles, and preparation contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles.
This analog derivative has the obvious suppression effect to bacterial growth, and therefore, the prospect that contains the very potential anti-bacterial drug of vanillin food grade,1000.000000ine mesh verivate conduct of thiadiazoles extremely merits attention.Along with 1; 3; Deepening continuously of 4-thiadiazoles and vanillin food grade,1000.000000ine mesh class drug research; On basis that its anti-microbial effect mechanism is constantly understood, carrying out effective structure of modification and modification and molecular designing, with have increasing efficiently, the vanillin food grade,1000.000000ine mesh class antibacterials that contain thiadiazoles of low toxicity are used for clinically, promote the well-being of mankind.
Summary of the invention
Technical problem to be solved by this invention provides one type of vanillin food grade,1000.000000ine mesh verivate, Its Preparation Method And Use of containing thiadiazoles, and this verivate has the obvious suppression effect to bacterium, can be used to prepare antibacterials.
One type of vanillin food grade,1000.000000ine mesh verivate that contains thiadiazoles of the present invention, this verivate has the general formula of following structure:
R in the formula
1, R
2, R
3For:
(1) R
1=R
2=H, R
3=NO
2Perhaps
(2) R
1=R
2=H, R
3=Br; Perhaps
(3) R
1=R
3=H, R
2=NO
2Perhaps
(4) R
2=R
3=H, R
1=Br; Perhaps
(5) R
1=R
2=Br, R
3=H; Perhaps
(6) R
1=Br, R
2=H, R
3=NO
2Perhaps
(7) R
1=R
3=H, R
2=OCH
3Perhaps
(8) R
1=R
2=H, R
3=OCH
3Perhaps
（9）R
2=R
3=H，R
1=NO
2。
One type of preparation method who contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles has following several kinds:
Method one:
(1) thiocarbanil is mixed according to mol ratio 1:1 ~ 2 with Hydrazine Hydrate 80, add organic solvent,, be cooled to the room temperature underpressure distillation and obtain solid at normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(2) solid that obtains in the step (1) is dissolved in the organic solvent, adds substituted vanillin food grade,1000.000000ine mesh, normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h, evaporated under reduced pressure obtains product; The solid mol ratio that obtains in substituted vanillin food grade,1000.000000ine mesh and the step (1) is 1:1; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(3) product that obtains in the step (2) is dissolved in organic solvent, adds catalyzer, evaporated under reduced pressure obtains crude product behind 70 ~ 90 degree backflows, 0.5 ~ 4h, the crude product recrystallization is obtained containing the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles; The mol ratio that obtains product in catalyzer and the step (2) is 0.05 ~ 0.5:1; Organic solvent is methyl alcohol or ethanol; Catalyzer is a ferric ammonium sulfate.
Method two:
(1) substituted vanillin food grade,1000.000000ine mesh is mixed according to mol ratio 1:1 ~ 2 with Hydrazine Hydrate 80, add organic solvent,, be cooled to the room temperature underpressure distillation and obtain solid at normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(2) solid that obtains in the step (1) is dissolved in the organic solvent, adds thiocarbanil, normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h, evaporated under reduced pressure obtains product; Solid that obtains in the step (1) and thiocarbanil mol ratio 1:1 ~ 2; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(3) product that obtains in the step (2) is dissolved in organic solvent, adds catalyzer, evaporated under reduced pressure obtains crude product behind 70 ~ 90 degree backflows, 0.5 ~ 4h, the crude product recrystallization is obtained containing the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles; The mol ratio that obtains product in catalyzer and the step (2) is 0.05 ~ 0.5:1; Organic solvent is methyl alcohol or ethanol; Catalyzer is a ferric ammonium sulfate.
Method three:
(1) substituted vanillin food grade,1000.000000ine mesh, Hydrazine Hydrate 80 and thiocarbanil are mixed according to mol ratio 1:1:1, add organic solvent, normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h, evaporated under reduced pressure obtains product; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(2) product that obtains in the step (1) is dissolved in organic solvent, adds catalyzer, evaporated under reduced pressure obtains crude product behind 70 ~ 90 degree backflows, 0.5 ~ 4h, the crude product recrystallization is obtained containing the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles; The mol ratio that obtains product in catalyzer and the step (1) is 0.05 ~ 0.5:1; Organic solvent is methyl alcohol or ethanol; Catalyzer is a ferric ammonium sulfate.
The described purposes that contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles is to can be used as antibacterials to use.
Beneficial effect of the present invention is following:
One type of vanillin food grade,1000.000000ine mesh verivate that contains thiadiazoles provided by the invention has the obvious suppression effect to bacterium, can be applied to prepare antibacterials, and this derivative preparation method is simple, and is easy to implement.
Embodiment
Below in conjunction with embodiment the present invention is done and to further describe.
Embodiment 1:
The preparation of 2-methoxyl group-3-nitro-4 [5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol (adopting the method two preparation).
With 2-NO
2-vanillin food grade,1000.000000ine mesh (10mmol) is dissolved in 25mL methyl alcohol, places the round-bottomed flask that has reflux.Add the 15mmol Hydrazine Hydrate 80, the oil bath heating at 75 ℃ of refluxed reaction 4h, is cooled to room temperature.The solvent evaporated under reduced pressure, chloroform extraction, organic layer is used anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure obtains product.Product (5mmol) is dissolved in the 25mL ethanol; Add the 5.5mmol thiocarbanil then, 80 ℃ of back flow reaction 4 hours, solvent evaporated under reduced pressure; The product that obtains is dissolved in 20mL ethanol; The ferric ammonium sulfate that adds 5mmol heats 80 ℃ of back flow reaction evaporated under reduced pressure solvent after 4 hours, and product gets target compound 1 with the absolute ethyl alcohol recrystallization.
Embodiment 2:
The preparation of 2-methoxyl group-3-bromo-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol (one preparation of employing method).
(10mmol) is dissolved in the 25mL chloroform with thiocarbanil, places the round-bottomed flask that has reflux.Add the 15mmol Hydrazine Hydrate 80, the oil bath heating at 75 ℃ of refluxed reaction 5h, is cooled to room temperature.The solvent evaporated under reduced pressure obtains product.Product (5mmol) is dissolved in the 25mL ethanol, adds 5mmol 2-bromo-vanillin food grade,1000.000000ine mesh then, 80 ℃ of back flow reaction 4 hours, the solvent evaporated under reduced pressure, chloroform extraction, organic layer is used anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure obtains product.The product that obtains is dissolved in 20mL ethanol, adds the ferric ammonium sulfate of 5mmol, heating reflux reaction is the evaporated under reduced pressure solvent after 4 hours, and product gets target compound 2 with the absolute ethyl alcohol recrystallization.
Embodiment 3:
The preparation of 6-bromo-2-methoxyl group-3-nitro-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol (three preparations of employing method).
With thiocarbanil (10mmol), 2-nitro-5-bromo-vanillin food grade,1000.000000ine mesh (10mmol) and Hydrazine Hydrate 80 (10mmol) are dissolved in 25mL ethanol, and heating reflux reaction is after 4 hours, the solvent evaporated under reduced pressure, and chloroform extraction, organic layer is used anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure obtains product.The product that obtains is dissolved in 20mL ethanol, adds the ferric ammonium sulfate of 10mmol, heating reflux reaction is the evaporated under reduced pressure solvent after 4 hours, and product gets target compound 3 with the absolute ethyl alcohol recrystallization.
Embodiment 4:
The preparation of 2-methoxyl group-5-nitro-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol (adopting the method two preparation).
(10mmol) is dissolved in 25mL methyl alcohol with 6-nitro-vanillin food grade,1000.000000ine mesh, places the round-bottomed flask that has reflux.Add the 15mmol Hydrazine Hydrate 80, the oil bath heating at 90 ℃ of refluxed reaction 2h, is cooled to room temperature.The solvent evaporated under reduced pressure, chloroform extraction, organic layer is used anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure obtains product.Product (5mmol) is dissolved in the 25mL ethanol; Add the 5.5mmol thiocarbanil then, 60 ℃ of back flow reaction 6 hours, solvent evaporated under reduced pressure; The product that obtains is dissolved in 20mL ethanol; The ferric ammonium sulfate that adds 5mmol heats 80 ℃ of back flow reaction evaporated under reduced pressure solvent after 4 hours, and product gets target compound 4 with the absolute ethyl alcohol recrystallization.
Embodiment 5:
The preparation of 2-methoxyl group-5-bromo-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol (one preparation of employing method).
(10mmol) is dissolved in the 25mL chloroform with thiocarbanil, places the round-bottomed flask that has reflux.Add the 15mmol Hydrazine Hydrate 80, the oil bath heating at 75 ℃ of refluxed reaction 5h, is cooled to room temperature.The solvent evaporated under reduced pressure obtains product.Product (5mmol) is dissolved in the 25mL ethanol, adds 5mmol 6-bromo-vanillin food grade,1000.000000ine mesh then, 90 ℃ of back flow reaction 2 hours, the solvent evaporated under reduced pressure, chloroform extraction, organic layer is used anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure obtains product.The product that obtains is dissolved in 20mL ethanol, adds the ferric ammonium sulfate of 5mmol, heat 80 ℃ of back flow reaction evaporated under reduced pressure solvent after 4 hours, product gets target compound 5 with the absolute ethyl alcohol recrystallization.
Embodiment 6:
6-methoxyl group-2, the preparation of 3-two bromo-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol.
The preparation method is with embodiment 2.With 5,6-two bromo-vanillin food grade,1000.000000ine meshs replace 2-bromo-vanillin food grade,1000.000000ine mesh, get target compound 6.
Embodiment 7:
2, the preparation of 5-dimethoxy-4 '-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol.
The preparation method is with embodiment 1.Replace 2-nitro-vanillin food grade,1000.000000ine mesh with 6-methoxyl group-vanillin food grade,1000.000000ine mesh, get target compound 7.
Embodiment 8:
2, the preparation of 3-dimethoxy-4 '-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol.
The preparation method is with embodiment 1.Replace 2-nitro-vanillin food grade,1000.000000ine mesh with 2-methoxyl group-vanillin food grade,1000.000000ine mesh, get target compound 8.
Embodiment 9:
The preparation of 2-methoxyl group-6-nitro-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol.
The preparation method is with embodiment 1.Replace 2-nitro-vanillin food grade,1000.000000ine mesh with 5-nitro-vanillin food grade,1000.000000ine mesh, get target compound 9.
Embodiment 10:
The preparation of 6-methoxyl group-2-bromo-4-[5-(anilino)-1,3,4-thiadiazoles-2-yl] phenol.
The preparation method is with embodiment 1.Replace 2-bromo-vanillin food grade,1000.000000ine mesh with 5-bromo-vanillin food grade,1000.000000ine mesh, get target compound 10.
Embodiment 11: the vanillin food grade,1000.000000ine mesh derivative antibacterial activity research that contains thiadiazoles
1. experiment material and method
1.1 medicine and reagent
Mueller-Hinton substratum (beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g; Agar 12.5g adds in the 1000mL zero(ppm) water), kantlex, penicillium mould, DMSO, MTT (3-(4,5-Er Jia Ji oxazole-2)-2; 5-phenylbenzene tetrazole bromine salt; Commodity oxazole by name is blue), Virahol, hydrochloric acid, be AR, synthetic compound 1 ~ 10, PBS damping fluid (phosphate buffered saline buffer 0.01mol/L, pH7.4, Na
2HPO
4.12H
2O 2.9g, KH
2PO
40.2g, NaCl 8.0g, KCl 0.2g, zero(ppm) water 1000mL).
1.2 bacterial classification
Intestinal bacteria (E.coli), streptococcus aureus (S.aureus), subtilis (B.subtilis), Pseudomonas aeruginosa (P.aeruginosa)
1.3 experimental technique
1.3.1 culture medium preparation
Get beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g, agar 12.5g adds in the 1000mL zero(ppm) water, the heated and boiled dissolving, packing, 121 ℃ of autoclavings 15 minutes are subsequent use.
1.3.2 the cultivation of test organisms
In sterilisable chamber, get intestinal bacteria, streptococcus aureus; Four kinds of test strains of subtilis and Pseudomonas aeruginosa, under the spirit lamp with inoculating needle respectively on four kinds of test strain inclined-planes, scrape the inclined-plane lawn that takes a morsel; Process bacteria suspension with a certain amount of sterilized water, get a certain amount of being added to then and melt and be cooled in the MH substratum about 50 ℃, shake up; At once pour in the sterile petri dish, treat after the abundant condensation with after the plug sealing, in 37 ℃ cultivate 18-24 hour subsequent use.Draw bacterium liquid 1mL, press the 1:1000 dilution, make bacterial concentration be about 10 with the MH substratum
5Cfu/mL.
1.3.3 antibacterial experiment:
Medicine to be measured is dissolved in the solution that is mixed with 2mg/mL among the DMSO, with doubling dilution medicine is diluted among finite concentration gradient (50 μ g/mL, 25 μ g/mL, 12.5 μ g/mL, 3.125 μ g/mL) and the DMSO then.In sterilization microtiter plate article one, add the substratum of 100 μ L respectively, the positive contrast of second adds 100 μ L bacteria suspensions.Add the bacteria suspension of 90 μ L and the medicament solution of 10 μ L in remaining hole.Parallel 3 times of each medicament solution concentration.Indicate bacteria name in the microtiter plate bottom.The petridish of handling is cultivated 24h, observation in 37 ℃.
1.3.4MIC mensuration
After each microtiter plate can be measured its MIC value intuitively, in each hole of plate, add 50 μ L PBS damping fluid (phosphate buffered saline buffer 0.01mol/L, pH7.4, Na
2HPO
4.2H
2O 2.9g, KH
2PO
40.2g, NaCl 8.0g, KCl0.2g, zero(ppm) water 1000mL), wherein comprise 2mg MTT/mL.At room temperature continue to hatch 4-5h.Material in the hole is shifted out and add the Virahol that 100 μ L contain 5%1mol/L HCl extract dyestuff.Continue at room temperature to compose to educate 12h, measure each hole photoabsorption (OD value), measure wavelength 550nm in ELIASA.Calculate the minimum inhibition concentration of medicine according to each hole OD value to bacterial growth.
Minimum inhibition concentration (minimum inhibitory concentration; MIC): under specific environment, hatched 24 hours; Can suppress the lowest drug concentration that to rise appreciably appear in certain mikrobe is minimum inhibition concentration; According to the optical density(OD) of measuring (OD value), make the typical curve of bacterial growth inhibiting rate, on typical curve, try to achieve its corresponding drug level.
2. experimental result
The MIC that records sees shown in the table 1:
The listed inhibition MIC value (μ g/mL) that contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles to bacterium of table 1 the present invention
Kanamycin: positive control.
Claims (5)
1. one type of vanillin food grade,1000.000000ine mesh verivate that contains thiadiazoles is characterized in that this verivate has the general formula of following structure:
R in the formula
1, R
2, R
3For:
(1) R
1=R
2=H, R
3=NO
2Perhaps
(2) R
1=R
2=H, R
3=Br; Perhaps
(3) R
1=R
3=H, R
2=NO
2Perhaps
(4) R
2=R
3=H, R
1=Br; Perhaps
(5) R
1=R
3=H, R
2=Br; Perhaps
(6) R
1=Br, R
2=H, R
3=NO
2Perhaps
(7) R
1=R
3=H, R
2=OCH
3Perhaps
(8) R
1=R
2=H, R
3=OCH
3Perhaps
（9）R
2=R
3=H，R
1=NO
2。
2. the described preparation method who contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles of claim 1 is characterized in that comprising the steps:
(1) thiocarbanil is mixed according to mol ratio 1:1 ~ 2 with Hydrazine Hydrate 80, add organic solvent,, be cooled to the room temperature underpressure distillation and obtain solid at normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(2) solid that obtains in the step (1) is dissolved in the organic solvent, adds substituted vanillin food grade,1000.000000ine mesh, normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h, evaporated under reduced pressure obtains product; The solid mol ratio that obtains in substituted vanillin food grade,1000.000000ine mesh and the step (1) is 1:1; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(3) product that obtains in the step (2) is dissolved in organic solvent, adds catalyzer, evaporated under reduced pressure obtains crude product behind 70 ~ 90 degree backflows, 0.5 ~ 4h, the crude product recrystallization is obtained containing the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles; The mol ratio that obtains product in catalyzer and the step (2) is 0.05 ~ 0.5:1; Organic solvent is methyl alcohol or ethanol; Catalyzer is a ferric ammonium sulfate.
3. the described preparation method who contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles of claim 1 is characterized in that comprising the steps:
(1) substituted vanillin food grade,1000.000000ine mesh is mixed according to mol ratio 1:1 ~ 2 with Hydrazine Hydrate 80, add organic solvent,, be cooled to the room temperature underpressure distillation and obtain solid at normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(2) solid that obtains in the step (1) is dissolved in the organic solvent, adds thiocarbanil, normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h, evaporated under reduced pressure obtains product; Solid that obtains in the step (1) and thiocarbanil mol ratio 1:1 ~ 2; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(3) product that obtains in the step (2) is dissolved in organic solvent, adds catalyzer, evaporated under reduced pressure obtains crude product behind 70 ~ 90 degree backflows, 0.5 ~ 4h, the crude product recrystallization is obtained containing the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles; The mol ratio that obtains product in catalyzer and the step (2) is 0.05 ~ 0.5:1; Organic solvent is methyl alcohol or ethanol; Catalyzer is a ferric ammonium sulfate.
4. the described preparation method who contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles of claim 1 is characterized in that comprising the steps:
(1) substituted vanillin food grade,1000.000000ine mesh, Hydrazine Hydrate 80 and thiocarbanil are mixed according to mol ratio 1:1:1, add organic solvent, normal temperature or 35 ~ 90 degree refluxed reactions, 0.2 ~ 12h, evaporated under reduced pressure obtains product; Organic solvent is methyl alcohol, ethanol or acetonitrile;
(2) product that obtains in the step (1) is dissolved in organic solvent, adds catalyzer, evaporated under reduced pressure obtains crude product behind 70 ~ 90 degree backflows, 0.5 ~ 4h, the crude product recrystallization is obtained containing the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles; The mol ratio that obtains product in catalyzer and the step (1) is 0.05 ~ 0.5:1; Organic solvent is methyl alcohol or ethanol; Catalyzer is a ferric ammonium sulfate.
5. the described purposes that contains the vanillin food grade,1000.000000ine mesh verivate of thiadiazoles of claim 1 is characterized in that using as antibacterials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210258898.3A CN102757405B (en) | 2012-07-25 | 2012-07-25 | Vanilline derivative containing thiadiazole, preparation method and purpose thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210258898.3A CN102757405B (en) | 2012-07-25 | 2012-07-25 | Vanilline derivative containing thiadiazole, preparation method and purpose thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102757405A true CN102757405A (en) | 2012-10-31 |
| CN102757405B CN102757405B (en) | 2014-04-16 |
Family
ID=47052087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210258898.3A Expired - Fee Related CN102757405B (en) | 2012-07-25 | 2012-07-25 | Vanilline derivative containing thiadiazole, preparation method and purpose thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102757405B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883159A (en) * | 2017-01-25 | 2017-06-23 | 东华大学 | A kind of ultraviolet probe of Thiourea and its preparation and application |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002022613A1 (en) * | 2000-09-14 | 2002-03-21 | Pantherix Limited | 3-(heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents |
| CN1861585A (en) * | 2005-05-12 | 2006-11-15 | 青岛科技大学 | Process of preparing 3-substituted 5-azo substituting group substituted-[1,3,4]-thia-dizole-2-thione |
| US20100298387A1 (en) * | 2006-12-05 | 2010-11-25 | Smithkline Beecham Corporation | IL-8 Receptor Antagonists |
| CN102276553A (en) * | 2011-06-23 | 2011-12-14 | 湖南科技大学 | 2-((1,3,4- thiadiazolyl)aminomethyl) phenol compound with bactericidal activity |
-
2012
- 2012-07-25 CN CN201210258898.3A patent/CN102757405B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002022613A1 (en) * | 2000-09-14 | 2002-03-21 | Pantherix Limited | 3-(heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents |
| CN1861585A (en) * | 2005-05-12 | 2006-11-15 | 青岛科技大学 | Process of preparing 3-substituted 5-azo substituting group substituted-[1,3,4]-thia-dizole-2-thione |
| US20100298387A1 (en) * | 2006-12-05 | 2010-11-25 | Smithkline Beecham Corporation | IL-8 Receptor Antagonists |
| CN102276553A (en) * | 2011-06-23 | 2011-12-14 | 湖南科技大学 | 2-((1,3,4- thiadiazolyl)aminomethyl) phenol compound with bactericidal activity |
Non-Patent Citations (3)
| Title |
|---|
| JOSHI, M. D.，等: "Studies on the synthesis and antimicrobial effect of some thiosemicarbazones and their related 1,3,4-thiadiazolines", 《CHEMICAL & ENVIRONMENTAL RESEARCH》 * |
| N. C. DESAI，等: "Preparation of some important medicinal compounds. Thiosemicarbazones, thiadiazolines, 4-thiazolidinones and 5-arylidene derivatives as antibacterial and tuberculostatic agents", 《JOURNAL OF THE INDIAN CHEMICAL SOCIETY》 * |
| 邹怀波，等: "香兰素苯腙的合成及热稳定性研究", 《宜春学院学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883159A (en) * | 2017-01-25 | 2017-06-23 | 东华大学 | A kind of ultraviolet probe of Thiourea and its preparation and application |
| CN106883159B (en) * | 2017-01-25 | 2018-10-02 | 东华大学 | A kind of ultraviolet probe of Thiourea and its preparation and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102757405B (en) | 2014-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2005014585A1 (en) | Halogenated quinazolinyl nitrofurans as antibacterial agents | |
| CN115521270B (en) | Malonate compound containing N-oxazolesulfonamide group, preparation method and application | |
| CN112645897A (en) | Thiazole derivative and preparation method and application thereof | |
| CN115677606B (en) | Chiral malonate compound, preparation and application thereof | |
| CN106518828A (en) | Amides myricetin derivative and preparation method and application thereof | |
| CN115322147B (en) | Benzenesulfonamide derivative, preparation method and application | |
| CN115232088B (en) | Thiazole sulfonamide derivative, preparation method and application thereof | |
| CN102757405B (en) | Vanilline derivative containing thiadiazole, preparation method and purpose thereof | |
| Yang et al. | Natural products-based insecticidal agents 20. Design, synthesis and insecticidal activity of novel honokiol/magnolol azo derivatives | |
| CN103524396A (en) | Diamidine derivative containing indole ring as well as preparation and method of derivative | |
| CN115232085B (en) | Malonate compound, preparation method and application thereof | |
| CN102746253A (en) | Oxadiazole derivative containing veratraldehyde and preparation method thereof | |
| CN103360370A (en) | Synthesis of nitroimidazole derivatives and application of nitroimidazole derivatives in field of antibacterial drugs | |
| CN103664690A (en) | Acylhydrazone derivatives of protocatechuic acid, and preparation method and antibacterial activity thereof | |
| CN102675302B (en) | Thiadiazole derivative containing 1,4-benzdioxanand preparation method and antibacterial activity thereof | |
| CN106554300A (en) | Application of the substituted isatin class compound in prevention and/or treatment bacterium infection medicine is prepared | |
| CN115521267A (en) | Benzenesulfonamide compound containing N-5-chloroisoxazole malonate structure, preparation method and application | |
| CN108017664A (en) | A kind of p-aminobenzene sulfonic acid metal complex antiseptic and its preparation method and application | |
| CN104892446A (en) | Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention | |
| CN101027299A (en) | Carbo- and hetero-cyclic antibiotics and use thereof | |
| CN101381357A (en) | 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity | |
| CN103319430A (en) | Pinane-based isoxazoline compound as well as synthesis method and application thereof | |
| CN103910680A (en) | Secnidazole derivatives, and preparation method thereof and application utilizing antibacterial activity thereof | |
| CN103910681A (en) | Metronidazole chalcone derivatives, and preparation method thereof and application utilizing antibacterial activity thereof | |
| CN105111138B (en) | Amphipathic molecule based on aryl substitution and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140416 Termination date: 20160725 |