CN103044352A - Thiazolidinone derivatives and preparation method thereof - Google Patents
Thiazolidinone derivatives and preparation method thereof Download PDFInfo
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- CN103044352A CN103044352A CN2011103089865A CN201110308986A CN103044352A CN 103044352 A CN103044352 A CN 103044352A CN 2011103089865 A CN2011103089865 A CN 2011103089865A CN 201110308986 A CN201110308986 A CN 201110308986A CN 103044352 A CN103044352 A CN 103044352A
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- obtains
- beautiful jade
- ketone derivatives
- under reduced
- reduced pressure
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Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 18
- 239000010977 jade Substances 0.000 claims description 18
- 150000002576 ketones Chemical class 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229960001701 chloroform Drugs 0.000 claims description 10
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 10
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 235000017281 sodium acetate Nutrition 0.000 claims description 10
- 239000001632 sodium acetate Substances 0.000 claims description 10
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 229960004756 ethanol Drugs 0.000 claims description 5
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 229940124350 antibacterial drug Drugs 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XWBTZHDDWRNOQH-UHFFFAOYSA-N 3-chloro-2-fluoroaniline Chemical class NC1=CC=CC(Cl)=C1F XWBTZHDDWRNOQH-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 206010011409 Cross infection Diseases 0.000 description 1
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003759 clinical diagnosis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention relates to thiazolidinone derivatives which are characterized by having the following general formula, wherein R is as designed in the specification. The thiazolidinone derivatives can be applied in preparing antibacterial drugs. A preparation method of the thiazolidinone derivatives is disclosed by the invention.
Description
Technical field
The present invention relates to class thiazole beautiful jade ketone derivatives and preparation method thereof.
Background technology.
Antibacterials are the most extensive and most important class medicines of present clinical application, continuous listing and the increase of bacterial resistance bacterial strain and the increase of resistance along with new variety, the sickness rate of hospital infection disease rises gradually, brings very large difficulty to aspects such as clinical diagnosis treatment and preventions.In recent years, antibacterials had had very great development, but the resistance phenomenon of new antimicrobial agent is also accompanied row thereupon, and the rational Application of antibacterials is day by day complicated.
Thiazole beautiful jade ketone and derivative thereof are owing to having pharmacology and the biological activity of wide spectrum, such as sterilization, anticonvulsion, antitumor, tuberculosis, pain relieving, anticancer and anti HIV-1 virus etc., simultaneously in organic synthesis, it or the good intermediate of a class, can be used for synthetic many bioactive compounds that have, can also be for the synthesis of fuel, liquid crystal material etc., and extremely chemist and medicine scholar's concern.Therefore, the present invention will prepare a class thiazole beautiful jade ketone derivatives.
This analog derivative is to the right significantly restraining effect of bacterial growth, and therefore, thiazole beautiful jade ketone derivatives extremely merits attention as the prospect of very potential anti-bacterial drug.Along with deepening continuously of thiazole beautiful jade ketone drug research, carry out effective structure of modification and modification and molecular designing on the basis that its anti-microbial effect mechanism is constantly understood, thiazole beautiful jade ketone antibacterials increasing efficient with having, low toxicity are used for clinical, promote the well-being of mankind.
Summary of the invention
The object of the present invention is to provide class thiazole beautiful jade ketone derivatives and their preparation method.
Technical scheme of the present invention is as follows:
One class thiazole beautiful jade ketone derivatives is characterized in that it has following general formula:
R is in the formula:
A kind of method for preparing an above-mentioned class thiazole beautiful jade ketone derivatives is characterized in that it is comprised of the following step:
Step 1. is the 0.01mol thiocarbanil, 0.01mol aniline, and the 20mL trichloromethane places the round-bottomed flask with reflux, and the oil bath heating is at 55 ℃ of lower back flow reaction 4h.
Step 2. adds water ethyl acetate extraction twice, the organic layer anhydrous Na with solvent trichloromethane evaporated under reduced pressure
2SO
4Evaporated under reduced pressure after dry obtains solid.
The solid that step 3. obtains step 2 is dissolved in the ethanol, then adds ethyl bromoacetate and sodium acetate, at 60 ℃ of lower back flow reaction 8h.Wherein the mol ratio of step 2 gained reactant and ethyl bromoacetate is 1: 3, with the mol ratio of sodium acetate be 1: 1.5.
After step 4. reacts completely, with adding water behind the etoh solvent evaporate to dryness, use ethyl acetate extraction, the organic layer anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure, the crude product that obtains obtains a class thiazole beautiful jade ketone derivatives of the present invention with the dehydrated alcohol recrystallization.
Embodiment
Further describe the present invention by following examples, but scope of the present invention is not subjected to any restriction of these embodiment.
Embodiment one: the preparation of 3-(4-fluoro-phenyl)-2-phenyl imido-thiazol-4-one (compound 1).
With the 0.01mol thiocarbanil, the 0.01mol para-fluoroaniline, the 20mL trichloromethane places the round-bottomed flask with reflux, and the oil bath heating is at 55 ℃ of lower back flow reaction 4h.With solvent trichloromethane evaporated under reduced pressure, add water ethyl acetate extraction twice, the organic layer anhydrous Na
2SO
4Evaporated under reduced pressure after dry obtains solid.The solid that obtains is dissolved in the ethanol, then adds ethyl bromoacetate and sodium acetate, at 60 ℃ of lower back flow reaction 8h.Wherein the mol ratio of gained solid and ethyl bromoacetate is 1: 3, with the mol ratio of sodium acetate be 1: 1.5.After reacting completely, with adding water behind the etoh solvent evaporate to dryness, use ethyl acetate extraction, the organic layer anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure, the crude product that obtains obtains a class thiazole beautiful jade ketone derivatives of the present invention with the dehydrated alcohol recrystallization.Buff powder, productive rate 60%, m.p.120-123 ℃; 1H NMR (300MHz, CDCl3): 4.17 (s, 2H); (6.86-6.92 m, 2H); (7.13-7.19 dd, J=8.4Hz, 2H); (7.31-7.52 m, 5H) .MS (ESI): 287.06 (C
15H
11FN
2OS, [M+H]+) .Anal.Calcd for C
15H
11FN
2OS:C, 62.92; H, 3.87; N, 9.78%.Found:C, 62.61; H, 3.73; N, 9.92%.
Embodiment two: the preparation of 3-(3-chloro-2-fluoro-phenyl)-2-phenyl imido-thiazol-4-one (compound 2).
With the 0.01mol thiocarbanil, 0.01mol 3-chloro-2 fluoroanilines, the 20mL trichloromethane places the round-bottomed flask with reflux, and the oil bath heating is at 55 ℃ of lower back flow reaction 4h.With solvent trichloromethane evaporated under reduced pressure, add water ethyl acetate extraction twice, the organic layer anhydrous Na
2SO
4Evaporated under reduced pressure after dry obtains solid.The solid that obtains is dissolved in the ethanol, then adds ethyl bromoacetate and sodium acetate, at 60 ℃ of lower back flow reaction 8h.Wherein the mol ratio of step 2 gained reactant and ethyl bromoacetate is 1: 3, with the mol ratio of sodium acetate be 1: 1.5.After reacting completely, with adding water behind the etoh solvent evaporate to dryness, use ethyl acetate extraction, the organic layer anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure, the crude product that obtains obtains a class thiazole beautiful jade ketone derivatives of the present invention with the dehydrated alcohol recrystallization.Pale yellow powder, productive rate 65%, m.p.129-130 ℃; 1HNMR (300MHz, CDCl3): 4.31 (s, 2H); (6.86-6.89 d, J=3.6Hz, 1H); (6.97-6.99 d, J=3.6Hz, 1H); (7.07-7.18 m, 1H); (7.28-7.32 t, J=3.3Hz, 1H); (7.34-7.47 m, 2H); (7.51-7.61 m, 2H) .MS (ESI): 321.02 (C
15H
10ClFN
2OS, [M+H]+) .Anal.Calcd forC
15H
11FN
2OS:C, 56.17; H, 3.14; N, 8.73%.Found:C, 56.23; H, 3.11; N, 8.63%.
Embodiment three: the preparation of 3-(3,5-3,5-dimethylphenyl)-2-phenyl imido-thiazol-4-one (compound 3).
With the 0.01mol thiocarbanil, 0.01mol 3, the 5-dimethoxyaniline, and the 20mL trichloromethane places the round-bottomed flask with reflux, and the oil bath heating is at 55 ℃ of lower back flow reaction 4h.With solvent trichloromethane evaporated under reduced pressure, add water ethyl acetate extraction twice, the organic layer anhydrous Na
2SO
4Evaporated under reduced pressure after dry obtains solid.The solid that obtains is dissolved in the ethanol, then adds ethyl bromoacetate and sodium acetate, at 60 ℃ of lower back flow reaction 8h.Wherein the mol ratio of step 2 gained reactant and ethyl bromoacetate is 1: 3, with the mol ratio of sodium acetate be 1: 1.5.After reacting completely, with adding water behind the etoh solvent evaporate to dryness, use ethyl acetate extraction, the organic layer anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure, the crude product that obtains obtains a class thiazole beautiful jade ketone derivatives of the present invention with the dehydrated alcohol recrystallization.White powder, productive rate 60%, m.p.195-196 ℃;
1HNMR (300MHz, CDCl
3): 2.32 (s, 6H); (4.14 s, 2H); (6.86 s, 1H); (6.88-6.89 m, 1H); (6.99 s, 2H); (7.08-7.12 dd, J=6.3Hz, 2H); (7.31-7.36 m, 2H) .MS (ESI): 329.09 (C
17H
16N
2O
3S, [M+H]+) .Anal.Calcd for C
17H
16N
2O
3S:C, 62.18; H, 4.91; N, 8.53%.Found:C, 61.99; H, 4.93; N, 8.63%.
Claims (3)
1. a class thiazole beautiful jade ketone derivatives is characterized in that it has following general formula:
R is in the formula:
2. method for preparing a class thiazole beautiful jade ketone derivatives claimed in claim 1 is characterized in that it is comprised of the following step:
Step 1. is the 0.01mol thiocarbanil, 0.01mol aniline, and the 20mL trichloromethane places the round-bottomed flask with reflux, and the oil bath heating is at 55 ℃ of lower back flow reaction 4h.
Step 2. adds water ethyl acetate extraction twice, the organic layer anhydrous Na with solvent trichloromethane evaporated under reduced pressure
2SO
4Evaporated under reduced pressure after dry obtains solid.
The solid that step 3. obtains step 2 is dissolved in the ethanol, then adds ethyl bromoacetate and sodium acetate, at 60 ℃ of lower back flow reaction 8h.Wherein the mol ratio of step 2 gained reactant and ethyl bromoacetate is 1: 3, with the mol ratio of sodium acetate be 1: 1.5.
After step 4. reacts completely, with adding water behind the etoh solvent evaporate to dryness, use ethyl acetate extraction, the organic layer anhydrous Na
2SO
4Drying, the solvent evaporated under reduced pressure, the crude product that obtains obtains a class thiazole beautiful jade ketone derivatives of the present invention with the dehydrated alcohol recrystallization.
3. the application of a class thiazole beautiful jade ketone derivatives claimed in claim 1 in the preparation antibacterials.
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|---|---|---|---|
| CN201110308986.5A CN103044352B (en) | 2011-10-13 | 2011-10-13 | Thiazolidinone derivatives and preparation method thereof |
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| CN103044352B CN103044352B (en) | 2015-04-29 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103588769A (en) * | 2013-11-04 | 2014-02-19 | 南京大学 | Synthesis of novel dihydrogen pyrazole-thiazolinone derivatives and application of dihydrogen pyrazole-thiazolinone derivatives in anticancer drugs |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2949457A (en) * | 1958-11-28 | 1960-08-16 | Ciba Pharm Prod Inc | Certain 2-phenyl-imino-3-phenyl-thiazolidine-4-ones |
| CN1055180A (en) * | 1990-03-27 | 1991-10-09 | 沃纳-兰伯特公司 | 3 of thiazolinone, azoles quinoline ketone and the imidazolone type that 2-replaces, the preparation method of 5-di-tert-butyl-hydroxy phenyl methylene derivatives |
| WO2009137133A2 (en) * | 2008-02-14 | 2009-11-12 | University Of Washington | 5-substituted-2-imino-thiazolidinone compounds and their use as inhibitors of bacterial infection |
-
2011
- 2011-10-13 CN CN201110308986.5A patent/CN103044352B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2949457A (en) * | 1958-11-28 | 1960-08-16 | Ciba Pharm Prod Inc | Certain 2-phenyl-imino-3-phenyl-thiazolidine-4-ones |
| CN1055180A (en) * | 1990-03-27 | 1991-10-09 | 沃纳-兰伯特公司 | 3 of thiazolinone, azoles quinoline ketone and the imidazolone type that 2-replaces, the preparation method of 5-di-tert-butyl-hydroxy phenyl methylene derivatives |
| WO2009137133A2 (en) * | 2008-02-14 | 2009-11-12 | University Of Washington | 5-substituted-2-imino-thiazolidinone compounds and their use as inhibitors of bacterial infection |
Non-Patent Citations (1)
| Title |
|---|
| RAM LAKHAN: "Potential Fungicides: Studies of 2-Arylimino-3-aryl-4-thiazolidinones, Their 1,1-Dioxides and 5-Phenylazo Derivatives", 《AGRIC. BIOL. CHEM.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103588769A (en) * | 2013-11-04 | 2014-02-19 | 南京大学 | Synthesis of novel dihydrogen pyrazole-thiazolinone derivatives and application of dihydrogen pyrazole-thiazolinone derivatives in anticancer drugs |
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| CN103044352B (en) | 2015-04-29 |
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Inventor after: Zhu Hailiang Inventor after: Sun Juan Inventor after: Zhang Yanbin Inventor after: Xiao Yu Inventor after: Yang Yushun Inventor after: Wang Xiaoliang Inventor after: Zhang Fei Inventor before: Zhu Hailiang Inventor before: Sun Juan Inventor before: Zhang Yanbin Inventor before: Yang Yushun Inventor before: Wang Xiaoliang Inventor before: Zhang Fei |
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Free format text: CORRECT: INVENTOR; FROM: ZHU HAILIANG SUN JUAN ZHANG YANBIN YANG YUSHUN WANG XIAOLIANG ZHANG FEI TO: ZHU HAILIANG SUN JUAN ZHANG YANBIN XIAO YU YANG YUSHUN WANG XIAOLIANG ZHANG FEI |
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