CN103360338A - Preparation method of chalconebenzothiazoleamide derivatives, and use of derivatives - Google Patents
Preparation method of chalconebenzothiazoleamide derivatives, and use of derivatives Download PDFInfo
- Publication number
- CN103360338A CN103360338A CN2013103241043A CN201310324104A CN103360338A CN 103360338 A CN103360338 A CN 103360338A CN 2013103241043 A CN2013103241043 A CN 2013103241043A CN 201310324104 A CN201310324104 A CN 201310324104A CN 103360338 A CN103360338 A CN 103360338A
- Authority
- CN
- China
- Prior art keywords
- cinnamophenone
- derivatives
- dissolved
- reaction
- benzothiazole
- 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
Abstract
The invention relates to a preparation method of chalconebenzothiazoleamide derivatives, and a use of the derivatives. The preparation method comprises the following steps: carrying out a ring closure reaction of a raw material different substituted aminochalcone, liquid bromine and potassium rhodanate under the catalysis of an acid to generate corresponding chalconebenzothiazoleamine; and reacting the chalconebenzothiazoleamine with benzoic acid under the action of condensing agents comprising N,N-dicyclohexyl carbodiimide, p-dimethylaminopyridine and 1-hydroxybenzotriazol to synthesize the derivatives. Results of experiments on the tyrosinase activity test of the above synthesized new compounds show that compounds 2d and 3b have certain tyrosinase activation activities, a compound 3d has a good tyrosinase activation activity, and the EC50 of the compound 3d is less than a positive medicine 8-methoxy psoralen. The method has the advantages of mild reaction conditions and simple experiment steps; and the chalconebenzothiazoleamide derivatives obtained through the method can be used for preparing leucoderma treatment medicines.
Description
Technical field
The present invention relates to a kind of preparation method and purposes of cinnamophenone benzothiazole amide derivatives, this analog derivative has the leukodermic pharmaceutical use for the treatment of through active test section compound.
Background technology
Flavonoid compound is extensive in distributed in nature, has multiple pharmacological effect, such as anti-inflammatory, analgesia, antibiotic, antiviral, and Green Tea Extract oxidation, antitumor, hepatoprotective effect etc.
Feverfew stem of Anthelmintic Ironweed (Ver-nohia anthelmintica L.) is the exclusive Chinese medicinal materials in Xinjiang, only be grown in Keshen, the Aksu Prefecture in Xinjiang, Uighur claims " card power cumin ", and the effect of dispersing cold for relieving pain, blood stasis dispersing and deswelling, desinsection nti-freckle is arranged.Stem of Anthelmintic Ironweed is clinical to be mainly used in treating vitiligo, and existing several compound mediciness take stem of Anthelmintic Ironweed as main component go on the market.As tie up medicine compound kaliziranding, insect-expelling saligna injection liquid, drive white etc.
Patent [CN200410091322.8] " purple fourth of the twelve Earthly Branches element and derivative thereof are in the purposes of preparation metabolism of pigment disease medicament ", find that purple fourth of the twelve Earthly Branches element and derivative thereof can improve tyrosinase activity, the propagation melanocyte, increase melanin content, especially can be used as treatment metabolism of pigment disease, such as the medicine of vitiligo and white hair; Patent [CN201210045334.1] " stem of Anthelmintic Ironweed flavonoid component and its production and use " is separated from stem of Anthelmintic Ironweed and is obtained purple fourth of the twelve Earthly Branches element, seven kinds of flavonoid components such as purple fourth of the twelve Earthly Branches florigen, and find that these compounds possess the leukodermic effect for the treatment of; The people such as F.Sonmez [Bioorg.Med.Chem.Lett.21 (2011) 7479-7482] then modify by 4 on the chalcone A ring, have obtained a series of new compounds that activate tyrosinase activity that have.
Thiazoles and benzothiazole compound be because having different biological activitys, such as desinsection, sterilization, weeding, plant growth regulating, antiviral etc.By thiazole and benzothiazole group are incorporated in the various compound structures not, can produce a series of compounds with broad-spectrum biological activity.
The present invention is at home and abroad on the basis about the analysis-by-synthesis of patent, document and this seminar previous research work; thiazole heterocycle is incorporated in the cinnamophenone molecule; again it is carried out benzoylation; thereby synthesized a series of cinnamophenone benzothiazole amides new compounds, and it has been carried out the tyrosinase activity screening.
Summary of the invention
The object of the invention is to, a kind of cinnamophenone benzothiazole amide derivatives preparation method and its usage is provided, this compounds is take different substituted-amino cinnamophenones as raw material, first under the katalysis of acid, generate corresponding cinnamophenone benzothiazole amine with bromine and potassium sulfocyanate generation ring closure reaction, more synthetic obtaining under the condensing agent effect.And the new compound that is synthesized carried out the tyrosinase activity test, experimental result shows: compound 2d, 3b have certain activation tyrosinase activity; Compound 3d has and activates preferably tyrosinase activity, its EC
50Less than positive drug 8-methoxy Psoralea corylifolia.The method reaction conditions is gentle, and experimental procedure is simple and direct.The cinnamophenone benzothiazole amide derivatives that obtains by the method for the invention is preparing the purposes for the treatment of in the vitiligo medicine.
A kind of cinnamophenone benzothiazole amide derivatives of the present invention, its structure is as leading to formula I:
Wherein when R ' was hydrogen, R was hydrogen, methyl, methoxyl group or chlorine; When R ' was benzoyl, R was hydrogen, methyl, methoxyl group or chlorine.
The preparation method of described cinnamophenone benzothiazole amide derivatives follows these steps to carry out:
A, amino cinnamophenone and potassium sulfocyanate that difference is replaced are dissolved in the dry glacial acetic acid, are stirred to whole dissolvings;
B, bromine is dissolved in the 2ml glacial acetic acid, under room temperature, slowly drop in the step a system, drip and finish the rear reaction that continues, after the TLC detection reaction is complete, reaction system is poured into water, be that 28% strong aqua is adjusted pH 9-10 with mass concentration, have solid to separate out, suction filtration dry the basic cinnamophenone benzothiazole amino derivative 2a-2d of different replacements;
C, with phenylformic acid and N, the N-dicyclohexylcarbodiimide is dissolved in dry N, in the dinethylformamide, under ice bath, stir 10min, to be dissolved in N to Dimethylamino pyridine and 1-hydroxy benzo triazole again, in the dinethylformamide, drop in the reaction system, react 30min under the ice bath, again the resulting cinnamophenone benzothiazole of step b amine 2a-2d is joined in the reaction system, continue to stir, naturally rise to room temperature reaction, after the TLC detection reaction is complete, the vacuum desolvation agent, residue is adopted the column chromatography gradient elution, and eluent is sherwood oil and ethyl acetate, namely gets cinnamophenone benzothiazole amide derivatives 3a-3d.
The volume ratio of eluent described in the step c is sherwood oil: ethyl acetate=5:1-3:1.
The purposes of the cinnamophenone benzothiazole amide derivatives that described method obtains in preparation treatment vitiligo medicine.
Cinnamophenone benzothiazole amide derivatives of the present invention is that thiazole heterocycle is incorporated in the cinnamophenone molecule, again it is carried out benzoylation, thus synthetic a series of cinnamophenone benzothiazole amide derivatives, and chemical equation is:
Wherein when R ' be that (H) time, R is hydrogen (H), methyl (CH to hydrogen
3), methoxyl group (OCH
3), chlorine (Cl); R ' is that (Bz) time, R is hydrogen (H), methyl (CH to benzoyl
3), methoxyl group (OCH
3), chlorine (Cl).
Embodiment
The present invention is further described according to embodiment, but the present invention is not limited only to these embodiment;
Reagent: all reagent are commercially available analytical pure;
Embodiment 1:(2 ' '-amino-2 ', 4 '-thiazolyl) preparation of cinnamophenone:
With 0.112g(0.5mmol) 4 '-amino cinnamophenone and 0.194g potassium sulfocyanate (2mmol) be dissolved in the dry glacial acetic acid, is stirred to whole dissolvings;
25 μ L bromines (0.25mmol) are dissolved in the 2ml glacial acetic acid, under room temperature, slowly drop in the step a system, drip and finish the rear reaction that continues, after the TLC detection reaction is complete, reaction system is poured into water, and is that 28% strong aqua is adjusted solution pH value 9-10 with mass concentration, has solid to separate out, suction filtration is dry to be got (2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2a) 0.115g;
(2 ' '-amino-2 ', 4 '-thiazolyl) the cinnamophenone nuclear magnetic data:
1H?NMR(400MHz,DMSO-d
6):δ8.59(s,1H),8.05(d,J=8.6Hz,1H),7.99(d,J=15.6Hz,1H),7.93(s,2H),7.88(d,J=4.8Hz,2H),7.72(d,J=15.6Hz,1H),7.48–7.40(m,4H)；
With 0.032g(0.27mmol) phenylformic acid and 0.056g(0.027mmol) N, the N-dicyclohexylcarbodiimide is dissolved in dry N, in the dinethylformamide, under ice bath, stir 10min, again with 0.033g(0.27mmol) to Dimethylamino pyridine and 0.037g(0.027mmol) the 1-hydroxy benzo triazole is dissolved in N, in the dinethylformamide, drop in the reaction system, react 30min under the ice bath, again with gained (2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2a) 0.07g(0.25mmol) join in the reaction system, continue to stir, naturally rise to room temperature reaction, after the TLC detection reaction is complete, the vacuum desolvation agent, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=3:1 column chromatography gradient elution, namely get (2 ' '-benzamido-2 ', 4 '-thiazolyl) cinnamophenone (3a) 0.062g;
(2 ' '-benzamido-2 ', 4 '-thiazolyl) nuclear magnetic data of cinnamophenone:
1H?NMR(400MHz,DMSO-d
6):δ13.15(s,1H),9.00(s,1H),8.24(dd,J=8.5,1.7Hz,1H),8.17(d,J=7.3Hz,2H),8.09(d,J=15.6Hz,1H),7.94–7.90(m,3H),7.80(d,J=15.6Hz,1H),7.69(t,J=7.4Hz,1H),7.59(t,J=7.7Hz,2H),7.50–7.47(m,3H)。
Embodiment 2:4-methyl-(2 ' '-amino-2 ', 4 '-thiazolyl) preparation of cinnamophenone
With 0.118g(0.5mmol) 4-methyl-4 '-amino cinnamophenone and 0.194g(2mmol) potassium sulfocyanate is dissolved in the dry glacial acetic acid, is stirred to whole dissolvings;
25 μ L bromines (0.25mmol) are dissolved in few 2ml glacial acetic acid, under room temperature, slowly drop in the step a system, drip and finish the rear reaction that continues, after the TLC detection reaction is complete, reaction system is poured into water, and is that 28% strong aqua is adjusted solution pH value 9-10 with mass concentration, has solid to separate out, suction filtration dry the 4-methyl-(2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2b) 0.128g;
The 4-methyl-(2 ' '-amino-2 ', 4 '-thiazolyl) the cinnamophenone nuclear magnetic data:
1H?NMR(400MHz,DMSO-d
6):δ8.59(s,1H),8.05(d,J=8.4Hz,1H),7.99–7.89(m,4H),7.78(d,J=7.8Hz,2H),7.69(d,J=15.5Hz,1H),7.42(d,J=8.5Hz,1H),7.28(d,J=7.9Hz,2H),2.36(s,5H)；
With 0.032g(0.27mmol) phenylformic acid and 0.056g(0.027mmol) N, the N-dicyclohexylcarbodiimide is dissolved in dry N, in the dinethylformamide, under ice bath, stir 10min, again with 0.033g(0.27mmol) to Dimethylamino pyridine and 0.037g(0.027mmol) the 1-hydroxy benzo triazole is dissolved in N, in the dinethylformamide, drop in the reaction system, react 30min under the ice bath, again with gained 4-methyl-(2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2b) 0.073g(0.25mmol) join in the reaction system, continue to stir, naturally rise to room temperature reaction, after the TLC detection reaction is complete, the vacuum desolvation agent, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=5:1 column chromatography gradient elution, namely get the 4-methyl-(2 ' '-benzamido-2 ', 4 '-thiazolyl) cinnamophenone (3b) 0.069g;
The 4-methyl-(2 ' '-benzamido-2 ', 4 '-thiazolyl) nuclear magnetic data of cinnamophenone:
1H?NMR(400MHz,DMSO-d
6):δ13.15(s,1H),9.00(s,1H),8.24(dd,J=8.5,1.7Hz,1H),8.17(d,J=7.4Hz,2H),8.04(d,J=15.5Hz,1H),7.92(d,J=8.2Hz,1H),7.83(d,J=8.0Hz,2H),7.77(d,J=15.5Hz,1H),7.70(t,J=7.4Hz,1H),7.60(t,J=7.7Hz,2H),7.31(d,J=7.9Hz,2H),2.38(s,3H)。
Embodiment 3:4-methoxyl group-(2 ' '-amino-2 ', 4 '-thiazolyl) preparation of cinnamophenone:
A, with 0.126g(0.5mmol) 4-methyl-4 '-amino cinnamophenone and 0.194g(2mmol) potassium sulfocyanate is dissolved in the dry glacial acetic acid, is stirred to whole dissolvings;
B, 25 μ L bromines (0.25mmol) are dissolved in the 2ml glacial acetic acid, under room temperature, slowly drop in the step a system, drip and finish the rear reaction that continues, after the TLC detection reaction is complete, reaction system is poured into water, and is that 28% strong aqua is adjusted solution pH value 9-10 with mass concentration, has solid to separate out, suction filtration dry the 4-methoxyl group-(2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2c) 0.141g;
The 4-methoxyl group-(2 ' '-amino-2 ', 4 '-thiazolyl) the cinnamophenone nuclear magnetic data:
1H?NMR(400MHz,DMSO-d
6):δ8.58(s,1H),8.05(d,J=8.5Hz,1H),7.95(s,1H),7.90–7.82(m,3H),7.70(d,J=15.4Hz,1H),7.42(d,J=8.5Hz,1H),7.02(d,J=8.6Hz,2H),3.83(s,1H)；
With 0.032g(0.27mmol) phenylformic acid and 0.056g(0.027mmol) N, the N-dicyclohexylcarbodiimide is dissolved in dry N, in the dinethylformamide, under ice bath, stir 10min, again with 0.033g(0.27mmol) to Dimethylamino pyridine and 0.037g(0.027mmol) the 1-hydroxy benzo triazole is dissolved in N, in the dinethylformamide, drop in the reaction system, react 30min under the ice bath, at last with embodiment 3 gained (the 4-methoxyl group-(2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2c) 0.077g(0.25mmol) join in the reaction system, continue to stir, naturally rise to room temperature reaction, after the TLC detection reaction is complete, the vacuum desolvation agent, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=5:1 column chromatography gradient elution, namely get the 4-methoxyl group-(2 ' '-benzamido-2 ', 4 '-thiazolyl) cinnamophenone (3c) 0.076g;
The 4-methoxyl group-(2 ' '-benzamido-2 ', 4 '-thiazolyl) nuclear magnetic data of cinnamophenone:
1H?NMR(400MHz,DMSO-d
6):δ13.14(s),8.97(s,1H),8.22(d,J=8.5Hz,1H),8.17(d,J=7.3Hz,2H),7.95(d,J=15.5Hz,1H),7.89(d,J=8.7Hz,3H),7.77(d,J=15.5Hz,1H),7.69(t,J=7.4Hz,1H),7.59(t,J=7.6Hz,2H),7.05(d,J=8.7Hz,2H),3.84(s,3H)。
Embodiment 4:4-chloro-(2 ' '-amino-2 ', 4 '-thiazolyl) preparation of cinnamophenone:
A, with 0.129g(0.5mmol) 4-methyl-4 '-amino cinnamophenone and 0.194g(2mmol) potassium sulfocyanate is dissolved in the dry glacial acetic acid, is stirred to whole dissolvings;
B, 25 μ L bromines (0.25mmol) are dissolved in the 2ml glacial acetic acid, under room temperature, slowly drop in the step a system, drip and finish the rear reaction that continues, after the TLC detection reaction is complete, reaction system is poured into water, and is that 28% strong aqua is adjusted solution pH value 9-10 with mass concentration, has solid to separate out, suction filtration dry the 4-chloro-(2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2d) 0.137g;
The 4-chloro-(2 ' '-amino-2 ', 4 '-thiazolyl) the cinnamophenone nuclear magnetic data:
1H?NMR(400MHz,DMSO-d
6):δ8.62(s,1H),8.35(s,2H),8.10(d,J=7.9Hz,1H),8.01(d,J=15.5Hz,1H),7.93(d,J=8.0Hz,2H),7.71(d,J=15.5Hz,1H),7.53(d,J=7.9Hz,2H),7.46(d,J=8.4Hz,1H)；
With 0.032g(0.27mmol) phenylformic acid and 0.056g(0.027mmol) N, the N-dicyclohexylcarbodiimide is dissolved in dry N, in the dinethylformamide, under ice bath, stir 10min, again with 0.033g(0.27mmol) to Dimethylamino pyridine and 0.037g(0.027mmol) the 1-hydroxy benzo triazole is dissolved in N, in the dinethylformamide, drop in the reaction system, react 30min under the ice bath, again with gained 4-chloro-(2 ' '-amino-2 ', 4 '-thiazolyl) cinnamophenone (2d) 0.079g(0.25mmol) join in the reaction system, continue to stir, naturally rise to room temperature reaction, after the TLC detection reaction is complete, the vacuum desolvation agent, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=4:1 column chromatography gradient elution, namely get the 4-methoxyl group-(2 ' '-benzamido-2 ', 4 '-thiazolyl) cinnamophenone (3d) 0.082g;
The 4-chloro-(2 ' '-benzamido-2 ', 4 '-thiazolyl) nuclear magnetic data of cinnamophenone:
1H?NMR(400MHz,DMSO-d
6):δ13.15(s),8.99(s,1H),8.23(d,J=8.5Hz,1H),8.17(d,J=7.5Hz,2H),8.11(d,J=15.6Hz,1H),7.97(d,J=8.3Hz,2H),7.89(d,J=8.5Hz,1H),7.78(d,J=15.6Hz,1H),7.68(t,J=7.2Hz,1H),7.61–7.51(m,4H)。
Embodiment 5
Invent described derivative and treat the biological activity determination of the purposes of leukodermic medicine as preparation:
The cinnamophenone benzothiazole amide derivatives 2a-2d and the 3a-3d that are synthesized are carried out the tyrosinase activity test:
Test philosophy: take L-Tyrosine(L-tyrosine) is substrate, measures different samples and promote tyrosine oxidase L-Tyrosine to be oxidized to the ability of DOPA quinone;
The material of test:
(1) substrate: TYR, Sigma-T3754,5g;
(2) enzyme: tyrosine oxidase, Sigma-T3824;
(3) damping fluid: 50mM phosphate buffered saline buffer;
(4) sample preparation: sample is dissolved in the dimethyl sulfoxide (DMSO), is mixed with suitable starting point concentration, take turns doing 5 times of dilutions with dimethyl sulfoxide (DMSO) again, each 5 weaker concn;
(4) positive control drug: 8-methoxyposoralen (8-MOP), Sigma-M3501,1g;
Method:
The preparation of specimen solution:
Each sample is dissolved in the dimethyl sulfoxide (DMSO) of 20-200 μ L, is mixed with the starting point concentration of 20mg/mL, then take turns doing 5 times of dilutions with dimethyl sulfoxide (DMSO), each 5 extent of dilution (concentration is followed successively by 80,16,3.2,0.64,0.13 μ g/mL);
The test of activation tyrosinase activity:
Adopt tyrosine oxidase DOPA speed oxidation style, be worth in 490nm place detection reaction product specificity absorbancy (A490) with enzyme-linked immunosorbent assay instrument;
In 96 well culture plates, react. total reaction system 200 μ L: specimen 2 μ L wherein, 50mM phosphate buffered saline buffer 60 μ L, 25U/ml tyrosine oxidase 40 μ L, the TYR 100 μ L of 2mM; Application of sample is complete, places the water bath of 37 ℃ of temperature to hatch 20min 96 well culture plates, measures every hole A490 value under microplate reader, each concentration three multiple hole; Calculate at last the activity ratio of tyrosine oxidase, tyrosine oxidase activity ratio=[(C-D)-(A-B)]/(A-B), wherein A is for adding the reaction system A490 value of not dosing of enzyme; B is the reaction system A490 value of not enzyme-added and medicine; C is for adding simultaneously the reaction system A490 value of enzyme and medicine; D is for only adding the not enzyme-added reaction system A490 value of medicine;
Use the said determination method, it is as shown in table 1 to record the active result of cinnamophenone benzothiazole amide derivatives 2a-2d of the present invention and 3a-3d:
Table 1 cinnamophenone benzothiazole amide derivatives 2a-2d and 3a-3d activate the activity data of tyrosine oxidase
EC
50: medium effective concentration.
Experimental result shows from table: compound 2d, 3b have certain activation tyrosinase activity; Compound 3d has and activates preferably tyrosinase activity, its EC
50Less than positive drug 8-methoxy Psoralea corylifolia.
Claims (4)
1. cinnamophenone benzothiazole amide derivatives, the structure that it is characterized in that this derivative are such as logical formula I:
Wherein when R ' was hydrogen, R was hydrogen, methyl, methoxyl group or chlorine; When R ' was benzoyl, R was hydrogen, methyl, methoxyl group or chlorine.
2. the preparation method of cinnamophenone benzothiazole amide derivatives according to claim 1 is characterized in that following these steps to carrying out:
A, amino cinnamophenone and potassium sulfocyanate that difference is replaced are dissolved in the dry glacial acetic acid, are stirred to whole dissolvings;
B, bromine is dissolved in the 2ml glacial acetic acid, under room temperature, slowly drop in the step a system, drip and finish the rear reaction that continues, after the TLC detection reaction is complete, reaction system is poured into water, be that 28% strong aqua is adjusted pH 9-10 with mass concentration, have solid to separate out, suction filtration dry the basic cinnamophenone benzothiazole amino derivative 2a-2d of different replacements;
C, with phenylformic acid and N, the N-dicyclohexylcarbodiimide is dissolved in dry N, in the dinethylformamide, under ice bath, stir 10min, to be dissolved in N to Dimethylamino pyridine and 1-hydroxy benzo triazole again, in the dinethylformamide, drop in the reaction system, react 30min under the ice bath, again the resulting cinnamophenone benzothiazole of step b amine 2a-2d is joined in the reaction system, continue to stir, naturally rise to room temperature reaction, after the TLC detection reaction is complete, the vacuum desolvation agent, residue is adopted the column chromatography gradient elution, and eluent is sherwood oil and ethyl acetate, namely gets cinnamophenone benzothiazole amide derivatives 3a-3d.
3. described method according to claim 2 is characterized in that eluent volume ratio described in the step c is sherwood oil: ethyl acetate=5:1-3:1.
One kind as claimed in claim 1 method obtain the purposes of cinnamophenone benzothiazole amide derivatives in preparation treatment vitiligo medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310324104.3A CN103360338B (en) | 2013-07-30 | 2013-07-30 | Preparation method of chalconebenzothiazoleamide derivatives, and use of derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310324104.3A CN103360338B (en) | 2013-07-30 | 2013-07-30 | Preparation method of chalconebenzothiazoleamide derivatives, and use of derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103360338A true CN103360338A (en) | 2013-10-23 |
| CN103360338B CN103360338B (en) | 2015-04-01 |
Family
ID=49362689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310324104.3A Active CN103360338B (en) | 2013-07-30 | 2013-07-30 | Preparation method of chalconebenzothiazoleamide derivatives, and use of derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103360338B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103923025A (en) * | 2014-04-16 | 2014-07-16 | 中国科学院新疆理化技术研究所 | Click chemistry based chalcone derivatives as well as preparation method and application |
| CN105801509A (en) * | 2016-05-03 | 2016-07-27 | 中国科学院新疆理化技术研究所 | Preparation method and application of phenylisoxazole-containing chalcone derivatives |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2244507A1 (en) * | 1973-06-26 | 1975-04-18 | Inst Nat Sante Rech Med | Chalcones and analogues - analgesics having low toxicity |
| US5179091A (en) * | 1990-06-22 | 1993-01-12 | Adir Et Compagnie | Chalcones |
| US6046212A (en) * | 1996-05-17 | 2000-04-04 | Kowa Co., Ltd. | Chalcone derivatives and drugs containing the same |
| CN1261349A (en) * | 1997-06-19 | 2000-07-26 | 英登纳股份有限公司 | Chalcones having antiproliferactive activity |
| WO2001098291A2 (en) * | 2000-06-20 | 2001-12-27 | Atherogenics, Inc. | 1,3-bis-(substituted-phenyl)-2-propen-1-ones and their use to treat vcam-1 mediated disorders |
| WO2003066608A1 (en) * | 2002-02-06 | 2003-08-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Catechol bioisosteres |
| WO2003076407A1 (en) * | 2002-03-14 | 2003-09-18 | The Walter And Eliza Hall Institute Of Medical Research | Novel chalcone derivatives and uses thereof |
-
2013
- 2013-07-30 CN CN201310324104.3A patent/CN103360338B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2244507A1 (en) * | 1973-06-26 | 1975-04-18 | Inst Nat Sante Rech Med | Chalcones and analogues - analgesics having low toxicity |
| US5179091A (en) * | 1990-06-22 | 1993-01-12 | Adir Et Compagnie | Chalcones |
| US6046212A (en) * | 1996-05-17 | 2000-04-04 | Kowa Co., Ltd. | Chalcone derivatives and drugs containing the same |
| CN1261349A (en) * | 1997-06-19 | 2000-07-26 | 英登纳股份有限公司 | Chalcones having antiproliferactive activity |
| WO2001098291A2 (en) * | 2000-06-20 | 2001-12-27 | Atherogenics, Inc. | 1,3-bis-(substituted-phenyl)-2-propen-1-ones and their use to treat vcam-1 mediated disorders |
| WO2003066608A1 (en) * | 2002-02-06 | 2003-08-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Catechol bioisosteres |
| WO2003076407A1 (en) * | 2002-03-14 | 2003-09-18 | The Walter And Eliza Hall Institute Of Medical Research | Novel chalcone derivatives and uses thereof |
Non-Patent Citations (5)
| Title |
|---|
| KAMAL A: "Synthesis of chalcone-amidobenzothiazole conjugates as antimitotic and apoptotic inducing agents", 《BIOORGANIC & MEDICINAL CHEMISTRY》, vol. 20, no. 11, 10 April 2012 (2012-04-10), XP028423305, DOI: doi:10.1016/j.bmc.2012.04.010 * |
| SONMEZ F ET AL: "Evaluation of new chalcone derivatives as polyphenol oxidase inhibitors", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》, vol. 21, no. 24, 19 October 2011 (2011-10-19) * |
| ZWAAGSTRA M E ET AL: "Synthesis and Structure-Activity Relationships of Carboxylated Chalcones: A Novel Series of CysLT 1 (LTD4) Receptor Antagonists", 《JOURNAL OF MEDICINAL CHEMISTRY》, vol. 40, no. 7, 1 February 1997 (1997-02-01) * |
| 廖头根 等: "新型查尔酮类化合物的合成及其生物活性研究", 《有机化学》, vol. 26, no. 5, 30 May 2006 (2006-05-30), pages 685 - 689 * |
| 张红: "新型查尔酮与黄酮醇类化合物的合成及其生物活性研究", 《中国优秀硕士学位论文全文数据库》, 15 October 2007 (2007-10-15) * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103923025A (en) * | 2014-04-16 | 2014-07-16 | 中国科学院新疆理化技术研究所 | Click chemistry based chalcone derivatives as well as preparation method and application |
| CN105801509A (en) * | 2016-05-03 | 2016-07-27 | 中国科学院新疆理化技术研究所 | Preparation method and application of phenylisoxazole-containing chalcone derivatives |
| CN105801509B (en) * | 2016-05-03 | 2018-01-05 | 中国科学院新疆理化技术研究所 | The preparation method and purposes of a kind of chalcone derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103360338B (en) | 2015-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107286077A (en) | A kind of selective C-KIT kinase inhibitors | |
| Xia et al. | Preparation of icariside II from icariin by enzymatic hydrolysis method | |
| CN107698575A (en) | The bifunctional molecule of novel B ET protein degradations ligand-mediated cereblon and its preparation and application | |
| Zhang et al. | Biotransformation of phlorizin by human intestinal flora and inhibition of biotransformation products on tyrosinase activity | |
| CN105037371A (en) | Deuterated indoleamine-2,3-dioxygenase inhibitor | |
| CN106061975A (en) | Pyrazolo[1,5-a]pyrimidines as antiviral compounds | |
| CN103342653B (en) | Preparation method and application of chalcone amide derivatives | |
| CN113735824A (en) | PROTAC for targeted degradation of tyrosinase and application thereof | |
| CN103360338B (en) | Preparation method of chalconebenzothiazoleamide derivatives, and use of derivatives | |
| CN106117166A (en) | The pharmaceutical composition of amrinone and the application in hypertension therapeutic thereof | |
| KR20090073227A (en) | Antiinflammatory agent comprising 2-aminophenol or derivative thereof as active ingredient | |
| CN102344475A (en) | Scutellarin derivative and preparation method and application thereof | |
| CN105384745A (en) | Crown ether cyclic quinazoline compound, preparation method therefor and application thereof in preparing tumor therapy and imaging drug | |
| CN101966194B (en) | New application of scutellarin and derivatives thereof | |
| CN101371869B (en) | Inhibitor originated from alpha-glucosidase of natto and preparation method thereof | |
| CN106543197B (en) | A kind of psoralen Schiff bases derivative and purposes | |
| JP2016222588A (en) | Tie2 ACTIVATOR, NEOVASCULARIZATION INHIBITOR, VASCULAR MATURATION AGEN, VASCULAR NORMALIZATION AGENT, VASCULAR STABILIZER, CLAUDIN-5 PRODUCTION PROMOTING AGENT, LYMPHANGIAL STABILIZER, eNOS PRODUCTION PROMOTING AGENT, VASODILATATOR, AND PLATELET-AGGREGATION-INHIBITOR AS WELL AS PHARMACEUTICAL COMPOSITIONS | |
| AU2018102217A4 (en) | Use of high-speed countercurrent chromatograph in bioconversion of glycoside component | |
| CN1332971C (en) | Luteolin-7-O-bata-glucuronide and its extracting process and application thereof | |
| CN105801509A (en) | Preparation method and application of phenylisoxazole-containing chalcone derivatives | |
| CN103613493A (en) | 4'-methoxyl chalcone compounds as well as preparation method and use thereof | |
| CN106590628A (en) | Specific fluorescent probe substrate of bilirubin metabolic enzyme UGT1A1 and preparation and application thereof | |
| CN105712958B (en) | A kind of Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe composition and preparation method and application | |
| CN104610276B (en) | Benzo [k, l] thioxanthene-3,4-dicarboxylic acid anhydride analog derivative-uridnine conjugate and its preparation method and application | |
| CN110269858B (en) | Twin medicine for treating ischemic stroke and preparation method 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 |