CN102757452A - [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan, preparation method and purpose thereof - Google Patents
[1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan, preparation method and purpose thereof Download PDFInfo
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Abstract
The invention belongs to the field of drug synthesis, and particularly relates to a [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan, a preparation method and a purpose thereof. The structural formula of the [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan refers to the patent specification. The preparation method comprises the following steps: reacting carbon disulfide and hydrazine hydrate at normal temperature, adding organic solvent to conduct reflux reaction to obtain thiocarbazide, carrying out the melt reaction on 1,4-benzdioxan-6-carboxylic acid and thiocarbazide to obtain an intermediate product, and performing the mixture reaction of intermediate product, substituted benzoic acid and phosphorus oxychloride to prepare the [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan. The [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan has a remarkable inhibiting effect, is efficient and non-toxic, and can be suitable for preparing antibacterials.
Description
Technical field
The present invention relates to thiadiazoles derivative, particularly a kind of [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles derivative, method for making and purposes that contains benzodioxan.
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 the important intermediate of producing medicine such as Kefzol, cefcanel, cefazedone, Cephanone, cefaparole, cynnematin BL-S339, BRL-16933; Since such medicine have antibiotic wide spectrum, good absorption, spinoff little, be particularly suited for characteristics such as oral absorption, be widely used clinically.
The someone reports 1 in the recent period, and it is active that the 4-benzodioxan also has certain antimicrobial antiphlogistic.Therefore; Along with deepening continuously of benzodioxan and triazolothiadiazole drug research; On the basis that its anti-microbial effect mechanism is constantly understood; Carry out effective structure of modification, modification and molecular designing, be used for clinically, promote the well-being of mankind having the increasing triazolothiadiazole antibacterials that contain benzodioxan efficient, low toxicity.
Summary of the invention
The object of the present invention is to provide a kind of [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles derivative, method for making and purposes of containing benzodioxan that bacterial growth is had obvious restraining effect, high-efficiency low-toxicity.
The present invention relates to one type of [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles derivative that contains benzodioxan, its general structure is following:
Wherein R is any one in the following groups:
One type of preparation method who contains [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles derivative of benzodioxan specifically may further comprise the steps:
(1) dithiocarbonic anhydride and Hydrazine Hydrate 80 normal temperature were reacted down 1-4 hour, add organic solvent, the oil bath heating, 70-120 ℃ of temperature refluxed reaction 0.5-2h is cooled to room temperature, and suction filtration obtains thiocarbohydrazide;
(2) with 1,4-benzodioxan-6-carboxylic acid and thiocarbohydrazide place round-bottomed flask, get intermediate product after the frit reaction;
(3) intermediate product that step (2) is obtained mixes with substituted benzoic acid, POCl3, and 80-150 ℃ is reacted 4-8h down, is cooled to room temperature, and suction filtration adds solvent recrystallization, obtains title product.
The mol ratio of said dithiocarbonic anhydride and Hydrazine Hydrate 80 is 1:2-1:3, and productive rate was the highest when usage ratio was 1:3.
Said organic solvent is water, methyl alcohol or ethanol.
Described 1, the mol ratio of 4-benzodioxan-6-carboxylic acid and thiocarbohydrazide is 1:1, and thiocarbohydrazide can be excessive a little, and its purpose is to reduce by product, is beneficial to purification.
The said melt temperature of step (2) is not less than 170 ℃, after the complete fusion of raw material, and stopping reaction 20-50min again.
The mol ratio of described intermediate product of step (3) and substituted benzoic acid is 1:1, and substituted benzoic acid also can be excessive a little.Temperature of reaction is 80-150 ℃, and the reaction times is 4-8h.
The described POCl3 of step (3) is a reaction solvent, consumption be can be under heating condition complete solubilizing reaction raw material.
Said recrystallization uses solvent to be methyl alcohol, ethanol, acetonitrile, ether, ETHYLE ACETATE or acetone.
The purposes of said verivate is to use as antibacterials.
Beneficial effect of the present invention is:
Thiadiazoles derivative has the obvious suppression effect to bacterium to [1,2,4] triazolo [3,4-b] [1,3,4] that contains benzodioxan of the present invention, and high effect nontoxic, can be applied to prepare antibacterials.
Embodiment
Below in conjunction with embodiment the present invention is further specified.
Embodiment 1
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(4-fluorophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The 2mol Hydrazine Hydrate 80 is placed the 100mL round-bottomed flask, slowly splash into the dithiocarbonic anhydride of 1mol under the ice bath.Remove ice bath after dropwising, normal temperature reacted 4 hours down.Add 50mL ethanol then, the oil bath heating, 75 ℃ of refluxed reaction 2h are cooled to room temperature.Get solid after the suction filtration drying.With solid that obtains (10mmol) and 10mmol1,4-benzodioxan-6-carboxylic acid is put into the 50mL round-bottomed flask, and 170 ℃ of fusions are stopping reaction 30min again, obtains intermediate product.The intermediate product of 1mmol and the parafluorobenzoic acid of 1mmol are added in the POCl3 of 10mL, and 100 ℃ are reacted 6h down.Be cooled to room temperature, pour the 100mL frozen water into, the solid that suction filtration is separated out, the absolute ethyl alcohol recrystallization gets target compound 1.
Embodiment 2
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(4-chloro-phenyl-)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The 2mol Hydrazine Hydrate 80 is placed the 100mL round-bottomed flask, slowly splash into the dithiocarbonic anhydride of 1mol under the ice bath.Remove ice bath after dropwising, normal temperature reacted 3 hours down.Add 50mL ethanol then, the oil bath heating, 90 ℃ of refluxed reaction 2h are cooled to room temperature.Get solid after the suction filtration drying.With the solid that obtains (10mmol) and 10mmol 1,4-benzodioxan-6-carboxylic acid is put into the 50mL round-bottomed flask, and 170 ℃ of fusions are stopping reaction 30min again, obtains intermediate product.The intermediate product of 1mmol and the Chlorodracylic acid of 1mmol are added in the POCl3 of 10mL, and 80 ℃ are reacted 8h down.Be cooled to room temperature, pour the 100mL frozen water into, the solid that suction filtration is separated out, the absolute ethyl alcohol recrystallization gets target compound 2.
Embodiment 3
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(4-bromophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The 2mol Hydrazine Hydrate 80 is placed the 100mL round-bottomed flask, slowly splash into the dithiocarbonic anhydride of 1mol under the ice bath.Remove ice bath after dropwising, normal temperature reacted 2 hours down.Add 50mL ethanol then, the oil bath heating, 100 ℃ of refluxed reaction 2h are cooled to room temperature.Get solid after the suction filtration drying.With solid that obtains (10mmol) and 10mmol1,4-benzodioxan-6-carboxylic acid is put into the 50mL round-bottomed flask, and 170 ℃ of fusions are stopping reaction 30min again, obtains intermediate product.The intermediate product of 1mmol and the parabromobenzoic acid of 1mmol are added in the POCl3 of 10mL, and 120 ℃ are reacted 4h down.Be cooled to room temperature, pour the 100mL frozen water into, the solid that suction filtration is separated out, the absolute ethyl alcohol recrystallization gets target compound 3.
Embodiment 4
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(4-tolyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with paratolunitrile with embodiment 1, gets target compound 4.
Embodiment 5
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(4-methoxyphenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein so that methoxy benzoic acid is replaced parafluorobenzoic acid, gets target compound 5 with embodiment 1.
Embodiment 6
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(4-nitrophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with p-Nitrobenzenecarboxylic acid with embodiment 1, gets target compound 6.
Embodiment 7
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(2-fluorophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with o-fluorobenzoic acid with embodiment 1, gets target compound 7.
Embodiment 8
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(2-chloro-phenyl-)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with 0-chloro-benzoic acid with embodiment 1, gets target compound 8.
Embodiment 9
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(2-bromophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with o-bromobenzoic acid with embodiment 1, gets target compound 9.
Embodiment 10
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(2-tolyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with ortho-toluic acid with embodiment 1, gets target compound 10.
Embodiment 11
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(2-methoxyphenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with adjacent methoxy benzoic acid with embodiment 1, gets target compound 11.
Embodiment 12
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(2-nitrophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with o-Carboxynitrobenzene with embodiment 1, gets target compound 12.
Embodiment 13
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(3-fluorophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with a fluorobenzoic acid with embodiment 1, gets target compound 13.
Embodiment 14
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(3-chloro-phenyl-)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with m-chlorobenzoic acid with embodiment 1, gets target compound 14.
Embodiment 15
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(3-bromophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with m-bromobenzoic acid with embodiment 1, gets target compound 15.
Embodiment 16
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(3-tolyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with meta-toluic acid with embodiment 1, gets target compound 16.
Embodiment 17
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(3-methoxyphenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with a methoxy benzoic acid with embodiment 1, gets target compound 17.
Embodiment 18
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(3-nitrophenyl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with M-NITROBENZOIC ACID with embodiment 1, gets target compound 18.
Embodiment 19
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(pyridin-4-yl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with Yi Yansuan with embodiment 1, gets target compound 19.
Embodiment 20
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(pyridin-3-yl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with nicotinic acid with embodiment 1, gets target compound 20.
Embodiment 21
3-(2,3-dihydrobenzo [b] [1,4] diox-6-yl)-6-(pyridine-2-yl)-5, the structural formula of 6-dihydro [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles is:
Its preparation method is:
The preparation method wherein replaces parafluorobenzoic acid with pyridine carboxylic acid with embodiment 1, gets target compound 21.
Embodiment 22
The activity research that contains [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles derivative of benzodioxan:
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 ~ 21, PBS damping fluid (phosphate buffered saline buffer 0.01mol/L, pH7.4, Na
2HPO
4.12H
2O2.9g, KH
2PO
40.2g, NaCl8.0g, 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
2O2.9g, KH
2PO
40.2g, NaCl8.0g, 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 verivate of table 1 the present invention is to the inhibition MIC value (μ g/mL) of bacterium
Kanamycin: positive control.
Claims (9)
1. one type of [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazoles derivative that contains benzodioxan is characterized in that its general structure is following:
Wherein R is any one in the following groups:
2. the preparation method of the said verivate of claim 1 is characterized in that may further comprise the steps:
(1), adds organic solvent again and carry out back flow reaction and obtain thiocarbohydrazide with the reaction down of dithiocarbonic anhydride and Hydrazine Hydrate 80 normal temperature;
(2) with 1,4-benzodioxan-6-carboxylic acid and thiocarbohydrazide frit reaction obtain intermediate product;
(3) intermediate product that step (2) is obtained and substituted benzoic acid, POCl3 hybrid reaction through suction filtration, recrystallization, make.
3. according to the preparation method of the said verivate of claim 2, it is characterized in that: the mol ratio of said dithiocarbonic anhydride and Hydrazine Hydrate 80 is 1:2-1:3, and the following reaction times of normal temperature is 1-4h, and the back flow reaction temperature is 70-120 ℃, reflux time 0.5-2h.
4. according to the preparation method of the said verivate of claim 2, it is characterized in that: said organic solvent is water, methyl alcohol or ethanol.
5. according to the preparation method of the said verivate of claim 2, it is characterized in that: said 1, the mol ratio of 4-benzodioxan-6-carboxylic acid and thiocarbohydrazide is 1:1.
6. according to the preparation method of the said verivate of claim 2, it is characterized in that: after the complete fusion of the described raw material of step (2), stopping reaction 20-50min again.
7. according to the preparation method of the said verivate of claim 2, it is characterized in that: the mol ratio of described intermediate product of step (3) and substituted benzoic acid is 1:1, and temperature of reaction is 80-150 ℃, and the reaction times is 4-8h.
8. according to the preparation method of the said verivate of claim 2, it is characterized in that: said recrystallization uses solvent to be methyl alcohol, ethanol, acetonitrile, ether, ETHYLE ACETATE or acetone.
9. the purposes of the said verivate of claim 1 is characterized in that using as antibacterials.
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| CN2012102588998A CN102757452A (en) | 2012-07-25 | 2012-07-25 | [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan, preparation method and purpose thereof |
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| CN2012102588998A CN102757452A (en) | 2012-07-25 | 2012-07-25 | [1,2,4] triazol [3,4-b][1,3,4] thiadiazole derivative containing benzdioxan, preparation method and purpose thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008060578A2 (en) * | 2006-11-15 | 2008-05-22 | Cytovia, Inc. | 3-aryl-6-aryl-[1,2,4] triazolo[3,4-b][1,3,4] thiadiazoles and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| US20090312374A1 (en) * | 2005-09-21 | 2009-12-17 | University Of Mysore | Derivatives of 4,6-disubstituted 1,2,4-triazolo- 1,3,4-thiadiazole, a process and uses thereof |
| CN102382127A (en) * | 2011-09-23 | 2012-03-21 | 复旦大学 | Myocardial small molecular compound for idiosyncratically promoting proliferation of myocardial cells and application thereof |
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- 2012-07-25 CN CN2012102588998A patent/CN102757452A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090312374A1 (en) * | 2005-09-21 | 2009-12-17 | University Of Mysore | Derivatives of 4,6-disubstituted 1,2,4-triazolo- 1,3,4-thiadiazole, a process and uses thereof |
| WO2008060578A2 (en) * | 2006-11-15 | 2008-05-22 | Cytovia, Inc. | 3-aryl-6-aryl-[1,2,4] triazolo[3,4-b][1,3,4] thiadiazoles and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| CN102382127A (en) * | 2011-09-23 | 2012-03-21 | 复旦大学 | Myocardial small molecular compound for idiosyncratically promoting proliferation of myocardial cells and application thereof |
Non-Patent Citations (4)
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Application publication date: 20121031 |