CN101928254B - Benzotriazole derivatives and preparation method and use thereof - Google Patents
Benzotriazole derivatives and preparation method and use thereof Download PDFInfo
- Publication number
- CN101928254B CN101928254B CN2010102229021A CN201010222902A CN101928254B CN 101928254 B CN101928254 B CN 101928254B CN 2010102229021 A CN2010102229021 A CN 2010102229021A CN 201010222902 A CN201010222902 A CN 201010222902A CN 101928254 B CN101928254 B CN 101928254B
- Authority
- CN
- China
- Prior art keywords
- preparation
- och
- acid
- triazole
- benzo
- 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.)
- Expired - Fee Related
Links
- KQUJLSQEOAMCOG-UHFFFAOYSA-N COc(cc12)ccc1nn[n]2OC(c1cc(OC)cc(OC)c1)=O Chemical compound COc(cc12)ccc1nn[n]2OC(c1cc(OC)cc(OC)c1)=O KQUJLSQEOAMCOG-UHFFFAOYSA-N 0.000 description 1
- CWPOLAXGIGTUMW-UHFFFAOYSA-N Oc1cc(O)cc(C([n]2nnc3c2cccc3)=O)c1 Chemical compound Oc1cc(O)cc(C([n]2nnc3c2cccc3)=O)c1 CWPOLAXGIGTUMW-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses benzotriazole derivatives, which are characterized by having the following general formula, wherein A=H or OCH3; R=H or OH or OCH3; and R'=H or OH or OCH3. The benzotriazole derivatives have higher antiproliferative activity on human oral epithelial cancer cells, lung cancer cells and gastric cancer cells. Therefore, the benzotriazole derivatives can be applied to preparing medicaments for resisting tumor cell proliferation. The invention discloses a preparation method for the benzotriazole derivatives.
Description
Technical field
The present invention relates to OR 10154 and preparation method thereof with in the application of preparation in the cancer therapy drug.
Background technology
In recent years, a large amount of research has disclosed the various biological activity and the clinical application potential of OR 10154, so they are one type of important potentiality medicines.Important pharmacological activities such as for example, the 1H-benzotriazole has anti-inflammatory, and is antiviral.4,5,6,7-tetrabromo-1H-benzotriazole (TBB) is the suppressor factor of a kind of extraordinary protein kinase C K2, it through with the allosteric binding site of nucleosides be used for bringing into play its effect.Steroidal C-17 benzoxazole has restraining effect to the growth of prostate tumor cells.The title complex that a kind of benzotriazole and bivalent cupric ion form, [2-(4,5-dihydro-1H-imidazolyl)-1H-benzotriazole]-dichloro copper shows the activity of very strong superoxide-dismutase (SOD), and seven kinds of human body tumour cell strains are had restraining effect.People have synthesized a series of [4-(2 hydrogen-1,2,3-benzotriazole base) phenoxy] paraffinic acid, and tested their biological activitys as px vegetation activated receptor (PPAR γ) agonist.PPAR γ is inhibited or induce its apoptotic effect to the growth of kinds of tumor cells and in-vivo tumour model.3-(1H-benzo [d] [1,2,3] triazole)-1-(4-p-methoxy-phenyl)-1-acetone-phenylformic acid (BmOB) can be pressed through increasing oxidation, follows injury of mitochondria to suppress the propagation of human liver cancer cell simultaneously.
Though benzotriazole and verivate thereof do not exist at occurring in nature, because that it has is antitumor, antimycotic, anti-inflammatory, antidepressants etc. are biological activity extensively, therefore its research as the potential drug lead compound is had bigger potentiality.
Summary of the invention
The object of the present invention is to provide one type of OR 10154 and their preparation method and purposes.
Technical scheme of the present invention is following:
One type of OR 10154 is characterized in that it has following general formula:
In the formula: A=H or OCH
3R=H or OH or OCH
3R '=H or OH or OCH
3
Above-mentioned OR 10154 is prepared by laxative remedy:
The preparation of 1H-benzo [d] [1,2,3]-triazole-1-alcohol:
The o-Nitrochlorobenzene that in the 1-of 10ml enanthol solution, adds 788mg slowly drips the Hydrazine Hydrate 80 of 1.2ml, in 110-120 ℃ of reaction 5h down; The sodium hydroxide solution neutralization reaction liquid of adding 40%, underpressure distillation is transferred between the pH to 3.2-3.5 with the hydrochloric acid of 1M; Filter out throw out, the methylene chloride recrystallization is used in the ice sodium chloride solution washing with 5% again; Obtain white crystal 1H-benzo [d] [1,2,3]-triazole-1-alcohol.
The preparation of 6-methoxyl group-1H-benzo [d] [1,2,3]-triazole-1-alcohol:
Method and 1H-benzo [d] [1,2,3]-triazole-1-alcohol similar; Only its used reactant is not an o-Nitrochlorobenzene, but 1-chloro-4-methoxyl group-2-oil of mirbane of 938mg, 6-methoxyl group-1H-benzo [d] [1 that reaction obtains; 2,3]-triazole-1-alcohol also is white crystal.
The preparation of 1H-benzo [d] [1,2,3]-triazole:
In the acetic acid soln of 10ml, add 541mg 1, the 2-phenylenediamine adds the sodium nitrite in aqueous solution of 25ml 1M again, in 70-80 ℃ of reaction 1h, and sodium hydroxide solution with 40% or the hydrochloric acid of 1M accent pH to 4.4-4.6.Filter, the ice sodium chloride solution washing precipitate with 5% is used the methylene chloride recrystallization, obtains white crystal 1H-benzo [d] [1,2,3]-triazole.
A kind of method for preparing OR 10154 of the present invention, it is in methylene dichloride, to add 1H-benzo [d] [1,2; 3]-triazole-1-alcohol, or 6-methoxyl group-1H-benzo [d] [1,2; 3]-triazole-1-alcohol, or 1H-benzo [d] [1,2; 3]-triazole, and then add phenylformic acid or hydroxyl or the substituted phenylformic acid of methoxyl group, and add 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (EDCHCl) as catalyzer; Ratio by amount of substance is 1: 1: 1.2 (benzotriazole cpd: phenylformic acid or substituted benzoic acid: raw material ratio reaction EDCHCl); Room temperature reaction 24h removes reaction solvent under the reduced pressure, and column chromatography purification obtains OR 10154 of the present invention.
The elutriant of the column chromatography described in the above-mentioned method for making is an ETHYLE ACETATE: the solution of sherwood oil=1: 1.
OR 10154 of the present invention, to the human oral cavity epithelial cancer cells, lung carcinoma cell and stomach cancer cell have stronger antiproliferative activity, and therefore, OR 10154 of the present invention can be used in the medicine of preparation anti-tumour cell proliferative.
Embodiment
Embodiment one: the preparation of 1H-benzo [d] [1,2,3]-triazole-1-alcohol
The o-Nitrochlorobenzene that in the 1-of 10ml enanthol solution, adds 788mg slowly drips the Hydrazine Hydrate 80 of 1.2ml, in 110-120 ℃ of reaction 5h down; The sodium hydroxide solution neutralization reaction liquid of adding 40%, underpressure distillation is transferred between the pH to 3.2-3.5 with the hydrochloric acid of 1M; Filter out throw out, the methylene chloride recrystallization is used in the ice sodium chloride solution washing with 5% again; Obtain white crystal 1H-1,2,3-benzotriazole-1-alcohol.Productive rate: 95%.Mp：155-157℃。
Embodiment two: the preparation of 6-methoxyl group-1H-benzo [d] [1,2,3]-triazole-1-alcohol
The preparation method is with instance one, and with 1-chloro-4-methoxyl group-2-oil of mirbane replacement o-Nitrochlorobenzene of 938mg, the white crystal that obtains is 6-methoxyl group-1H-1, and 2,3-benzotriazole-1-alcohol.Productive rate: 90%.Mp：169-171℃。
Embodiment three: the preparation of 1H-benzo [d] [1,2,3]-triazole
In the acetic acid soln of 10ml, add 541mg 1, the 2-phenylenediamine adds the sodium nitrite in aqueous solution of 25ml 1M again, in 70-80 ℃ of reaction 1h, and the hydrochloric acid accent pH to 4.4-4.6 of the sodium hydroxide solution/1M with 40%.Filter, the ice sodium chloride solution washing precipitate with 5% is used the methylene chloride recrystallization, obtains white crystal 1H-benzo [d] [1,2,3]-triazole.Productive rate: 90%.Mp：98-100℃。
Embodiment four: 3, the preparation of 5-resorcylic acid-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 1)
With product and 385mg 3 that 337mg embodiment one obtains, the 5-resorcylic acid joins in the 30ml methylene dichloride, adds 575mg EDCHCl as catalyzer, at room temperature reacts 24h.Reaction system is revolved dried, petrol ether/ethyl acetate=1: 1 is carried out column chromatography purification and is obtained white crystal and be final product.Productive rate: 75%.Mp：193-194℃.ESI?MS：272.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.11(d，J＝8.1Hz，1H，Bt?Ar-H)，7.60-7.57(m，1H，Bt?Ar-H)，7.46-7.41(m，2H，Bt?Ar-H)，7.46(d，J＝2.2Hz，2H，Ar-H)，6.90(d，J＝2.2Hz，1H，Ar-H).Anal.Calc?for?C
13H
9N
3O
4：C，57.57；H，3.34；N，15.49％.Found：C，57.42；H，3.61；N，15.32％.
Embodiment five: 3, the preparation of 5-dimethoxybenzoic acid-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 2)
The preparation method is with embodiment four, and with 3, the 5-dimethoxybenzoic acid replaces 3, and the 5-resorcylic acid obtains white crystal and is final product.Productive rate: 84%.Mp：162-163℃.ESI?MS：300.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.10(d，J＝8.2Hz，1H，Bt?Ar-H)，7.58-7.54(m，1H，Bt?Ar-H)，7.45-7.40(m，2H，BtAr-H)，7.36(d，J＝2.2Hz，2H，At-H)，6.86(d，J＝2.2Hz，1H，Ar-H)，3.98(s，6H，OCH
3).Anal.Calc?for?C
15H
13N
3O
4：C，60.20；H，4.38；N，14.04％.Found：C，60.26；H，4.16；N，14.28％.
Embodiment six: 3,4, the preparation of 5-trimethoxybenzoic acid-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 3)
The preparation method is with embodiment four, and with 3,4, the 5-trimethoxybenzoic acid replaces 3, and the 5-resorcylic acid obtains white crystal and is final product.Productive rate: 85%.Mp：175-176℃.ESI?MS：330.1([M+H]
+).
1H-NMR(CDCl
3)δ：8.12(1H，d，J＝8.4Hz，Bt?Ar-H)，7.60-7.54(1H，m，Bt?Ar-H)，7.52(2H，s，Ar-H)，7.50-7.43(2H，m，Bt?Ar-H)，4.00(3H，s，OCH
3)，3.97(6H，s，OCH
3).
13C-NMR(CDCl
3)δ：162.4，153.4(2C)，144.2，143.6，128.9，128.7，124.8，120.6，119.1，108.4，108.1(2C)，61.1，56.5(2C).EIMS(m/z)：212(100％)，197(56％)，195(27％)，119(12％)，91(9％).Anal.Calc?forC
16H
15N
3O
5：C，58.36；H，4.59；N，12.76.Found：C，58.65；H，4.62；N，12.64.
Embodiment seven: the preparation of phenylformic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 4)
Product and 305mg phenylformic acid that 413mg embodiment two is obtained join in the 30ml methylene dichloride, add 575mgEDCHCl as catalyzer, at room temperature react 24h.Reaction system is revolved dried, petrol ether/ethyl acetate=1: 1 is carried out column chromatography purification and is obtained white crystal and be final product.Productive rate: 81%.Mp：96-97℃.ESI?MS：270.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.26-8.24(m，2H，Ar-H)，8.02(d，J＝8.4Hz，1H，BtAr-H)，7.78-7.74(m，1H，Ar-H)，7.60-7.57(m，2H，Ar-H)，7.46-7.42(m，1H，Bt?Ar-H)，7.10-7.05(m，2H，Bt?Ar-H)，3.92(s，3H，OCH
3).Anal.Calc?for?C
14H
11N
3O
3：C，62.45；H，4.12；N，15.61％.Found：C，62.35；H，4.02；N，15.76％.
Embodiment eight: the preparation of 4-hydroxy-benzoic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 5)
The preparation method replaces phenylformic acid with embodiment seven with the 4-hydroxy-benzoic acid, obtains white crystal and is final product.Productive rate: 78%.Mp：185-186℃.ESI?MS：286.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.05(d，J＝8.2Hz，1H，Bt?Ar-H)，7.95(d，J＝8.4Hz，2H，Ar-H)，7.49-7.44(m，1H，Bt?Ar-H)，7.18-7.13(m，2H，Bt?Ar-H)，7.21(d，J＝8.4Hz，2H，Ar-H)，3.95(s，3H，Bt?OCH
3).Anal.Calc?forC
14H
11N
3O
4：C，58.95；H，3.89；N，14.73％.Found：C，58.81；H，3.78；N，14.85％.
Embodiment nine: 3, the preparation of 5-resorcylic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 6)
The preparation method is with embodiment seven, and with 3, the 5-resorcylic acid replaces phenylformic acid, obtains white crystal and is final product.Productive rate: 72%.Mp：205-206℃.ESI?MS：302.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.01(d，J＝8.4Hz，1H，Bt?Ar-H)，7.45-7.41(m，1H，Bt?Ar-H)，7.36(d，J＝2.3Hz，2H，Ar-H)，7.12-7.07(m，2H，Bt?Ar-H)，7.20(d，J＝8.5Hz，2H，Ar-H)，6.85(d，J＝2.3Hz，1H，Ar-H)，3.91(s，3H，Bt?OCH
3).Anal.Calc?for?C
14H
11N
3O
5:C，55.82；H，3.68；N，13.95％.Found：C，56.02；H，3.78；N，13.78％.
Embodiment ten: 3,4, the preparation of 5-trihydroxybenzoic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 7)
The preparation method is with embodiment seven, and with 3,4, the 5-trihydroxybenzoic acid replaces phenylformic acid, obtains white crystal and is final product.Productive rate: 68%.Mp：208-209℃.ESI?MS：318.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：7.99(d，J＝8.5Hz，1H，Bt?Ar-H)，7.58(s，2H，Ar-H)，7.49-7.45(m，1H，Bt?Ar-H)，7.36(d，J＝2.2Hz，2H，Ar-H)，7.21-7.15(m，2H，Bt?Ar-H)，3.95(s，3H，Bt?OCH
3).Anal.Calc?for?C
14H
11N
3O
6：C，53.00；H，3.49；N，13.24％.Found：C，53.07；H，3.62；N，13.05％.
Embodiment 11: the preparation of 4-methoxybenzoic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 8)
The preparation method replaces phenylformic acid with embodiment seven with the 4-methoxybenzoic acid, obtains white crystal and is final product.Productive rate: 83%.Mp：161-162℃.ESI?MS：300.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.03(d，J＝8.3Hz，1H，Bt?Ar-H)，7.92(d，J＝8.5Hz，2H，Ar-H)，7.47-7.43(m，1H，Bt?Ar-H)，7.15-7.12(m，2H，Bt?Ar-H)，7.18(d，J＝8.5Hz，2H，Ar-H)，4.02(s，3H，Ar?OCH
3)，3.93(s，3H，BtOCH
3).Anal.Calc?for?C
15H
13N
3O
4：C，60.20；H，4.38；N，14.04％.Found：C，60.02；H，4.56；N，13.92％.
Embodiment 12: 3, and the preparation of 5-dimethoxybenzoic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 9)
The preparation method is with embodiment seven, and with 3, the 5-dimethoxybenzoic acid replaces phenylformic acid, obtains white crystal and is final product.Productive rate: 85%.Mp：176-177℃.ESI?MS：330.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：7.98(d，J＝8.4Hz，1H，Bt?Ar-H)，7.44-7.40(m，1H，Bt?Ar-H)，7.32(d，J＝2.2Hz，2H，Ar-H)，7.10-7.06(m，2H，Bt?Ar-H)，7.18(d，J＝8.5Hz，2H，Ar-H)，6.82(d，J＝2.2Hz，1H，Ar-H)，3.96(s，6H，Ar?OCH
3)，3.88(s，3H，Bt?OCH
3).Anal.Calc?for?C
16H
15N
3O
5：C，58.36；H，4.59；N，12.76％.Found：C，58.55；H，4.74；N，12.41％.
Embodiment 13: 3,4, and the preparation of 5-trimethoxybenzoic acid-6-methoxyl group-1H-benzo [d] [1,2,3] triazole-1-alcohol ester (compound 10)
The preparation method is with embodiment seven, and with 3,4, the 5-trimethoxybenzoic acid replaces phenylformic acid, obtains white crystal and is final product.Productive rate: 81%.Mp：182-183℃.ESI?MS：360.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：7.96(d，J＝8.5Hz，1H，Bt?Ar-H)，7.55(s，2H，Ar-H)，7.46-7.42(m，1H，Bt?Ar-H)，7.32(d，J＝2.2Hz，2H，Ar-H)，7.18-7.14(m，2H，Bt?Ar-H)，4.02(s，3H，Ar?OCH
3)，3.99(s，6H，ArOCH
3)，3.91(s，3H，Bt?OCH
3).Anal.Calc?for?C
17H
17N
3O
6：C，56.82；H，4.77；N，11.69％.Found：C，56.71；H，4.88；N，11.42％.
Embodiment 14: the preparation of 1-(3,5-dihydroxy-benzene formyl radical)-1H-benzo [d] [1,2,3] triazole (compound 11)
With product and 385mg 3 that 298mg embodiment three obtains, the 5-resorcylic acid joins in the 30ml methylene dichloride, adds 575mg EDCHCl as catalyzer, at room temperature reacts 24h.Reaction system is revolved dried, petrol ether/ethyl acetate=1: 1 is carried out column chromatography purification and is obtained white crystal and be final product.Productive rate: 78%.Mp：144-145℃.ESI?MS：256.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.36(d，J＝8.4Hz，1H，Bt?Ar-H)，8.19-8.16(m，1H，Bt?Ar-H)，7.73-7.69(m，1H，Bt?Ar-H)，7.55-7.51(m，1H，Bt?Ar-H)，7.46(d，J＝2.3Hz，2H，At-H)，6.95(d，J＝2.3Hz，1H，Ar-H).Anal.Calc?for?C
13H
9N
3O
3：C，61.18；H，3.55；N，16.46％.Found：C，61.26；H，3.42；N，16.39％.
Embodiment 15: the preparation of 1-(3,4,5-trihydroxybenzene formyl radical)-1H-benzo [d] [1,2,3] triazole (compound 12)
The preparation method is with embodiment 14, and with 3,4, the 5-trihydroxybenzoic acid replaces 3, and the 5-resorcylic acid obtains white crystal and is final product.Productive rate: 75%.Mp：157-158℃.ESI?MS：272.1([M+H]
+).
1H?NMR(CDCl
3，δppm)：8.35(d，J＝8.3Hz，1H，Bt?Ar-H)，8.16-8.13(m，1H，Bt?Ar-H)，7.78-7.75(m，1H，Bt?Ar-H)，7.59-7.55(m，1H，Bt?Ar-H)，7.27(s，2H，At-H).Anal.Calc?for?C
13H
9N
3O
4：C，57.57；H，3.34；N，15.49％.Found：C，57.51；H，3.51；N，15.58％.
Embodiment 16: OR 10154 is to the antiproliferative activity research of three-type-person's tumour cell
(1) cultivation of tumour cell: culturing human oral epithelium KB cancer cells, lung cancer H460 cancer cells and cancer of the stomach MKN45 cancer cells in containing the RPMI-1640 substratum of 5% foetal calf serum.The cancer cells that will be in logarithmic phase is cultivated in No. 24 petridish with the density of every milliliter in 5000 cells.
(2) dosing: add the compound of different concns in the tumour cell of cultivating, continue to cultivate 72 hours.Use the methylene radical blue laws to go of the influence of evaluation test medicine to above-mentioned growth of tumour cell, through with the comparison of positive controls, obtain the 50% inhibition concentration (IC of compound to above-mentioned three kinds of tumour cells
50).Property of medicine control group medicine used herein is a Zorubicin.
OR 10154 of the present invention is to reaching positive controls to KB, the inhibition IC of H460 and MKN45 cancer cells
50Be worth as shown in the table.
Claims (4)
1. one type of OR 10154 is characterized in that it has following general formula:
In the formula: A=OCH
3R=H or OH or OCH
3R '=H or OH or OCH
3
2. method for preparing the described OR 10154 of claim 1; It is characterized in that: it is in methylene dichloride, to add 6-methoxyl group-1H-benzo [d] [1; 2; 3]-triazole-1-alcohol, and then add phenylformic acid or hydroxyl or the substituted phenylformic acid of methoxyl group, and add 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (EDCHCl) as catalyzer; Ratio by amount of substance is: benzotriazole cpd: the raw material ratio reaction of phenylformic acid or substituted benzoic acid: 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride=1: 1: 1.2; Room temperature reaction 24h removes reaction solvent under the reduced pressure, and column chromatography purification obtains OR 10154.
3. according to the said method for making of claim 2, it is characterized in that: the elutriant of described column chromatography is an ETHYLE ACETATE: the solution of sherwood oil=1: 1.
4. the described OR 10154 of claim 1 is in preparation oral squamous carcinoma cell, the application in the anti proliferative medicine of lung carcinoma cell and stomach cancer cell.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102229021A CN101928254B (en) | 2010-07-09 | 2010-07-09 | Benzotriazole derivatives and preparation method and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102229021A CN101928254B (en) | 2010-07-09 | 2010-07-09 | Benzotriazole derivatives and preparation method and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101928254A CN101928254A (en) | 2010-12-29 |
| CN101928254B true CN101928254B (en) | 2012-05-02 |
Family
ID=43367735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102229021A Expired - Fee Related CN101928254B (en) | 2010-07-09 | 2010-07-09 | Benzotriazole derivatives and preparation method and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101928254B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875483A (en) * | 2012-10-26 | 2013-01-16 | 陈守文 | Synthesis technique of benzotriazole |
| CN103848826A (en) * | 2012-11-30 | 2014-06-11 | 南京大学 | Preparation method and use of 1,3,4-oxadiazole derivative having benzotriazole structure |
| CN103848827A (en) * | 2012-11-30 | 2014-06-11 | 南京大学 | Application of benzotriazole derivatives in anti-cancer drugs |
| CN103848828A (en) * | 2012-11-30 | 2014-06-11 | 南京大学 | Application of oxadiazole derivatives in anti-cancer drugs |
| CN103450103A (en) * | 2013-05-08 | 2013-12-18 | 如皋市金陵化工有限公司 | Synthesis process of 1-hydroxybenzotriazole |
| CN109761961A (en) * | 2019-02-28 | 2019-05-17 | 贵州医科大学 | A kind of Benzotriazole Derivative is as Sirtuin inhibitor and its application |
| CN115043822A (en) * | 2022-06-23 | 2022-09-13 | 中国石油天然气集团有限公司 | Benzotriazole derivative, preparation method thereof, benzotriazole corrosion inhibitor and application thereof |
| CN115160314B (en) * | 2022-07-28 | 2023-12-05 | 南方医科大学 | Heterocyclic aromatic amide compound and preparation method and application thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1223921A2 (en) * | 1999-10-27 | 2002-07-24 | Sunol Molecular Corporation | Tissue factor antagonists and methods of use thereof |
| EP1589374B1 (en) * | 2004-02-26 | 2008-10-01 | FUJIFILM Corporation | Polymerizable composition and process for producing lithographic plate using the polymerizable composition |
| JP2006160836A (en) * | 2004-12-03 | 2006-06-22 | Fuji Photo Film Co Ltd | Ink for ink jet recording curable by irradiating with radioactive ray and method for making lithographic printing plate using the same |
-
2010
- 2010-07-09 CN CN2010102229021A patent/CN101928254B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101928254A (en) | 2010-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101928254B (en) | Benzotriazole derivatives and preparation method and use thereof | |
| Abdelgawad et al. | New pyrimidine-benzoxazole/benzimidazole hybrids: Synthesis, antioxidant, cytotoxic activity, in vitro cyclooxygenase and phospholipase A2-V inhibition | |
| CN105037355B (en) | The indazole inhibitors and its therapeutical uses of Wnt signal transduction paths | |
| WO2018019084A1 (en) | Benzamide compound and use thereof in preparing drugs inhibiting cancer cell proliferation and/or treating cancer | |
| JP5649652B2 (en) | Substituted hydrazide compounds and their applications | |
| CN102850283B (en) | Triazolyl-containing amino-dithio formic ether compound as well as preparation method and application of compound | |
| CN101121711A (en) | Pyrazolcarbazone derivatives and application thereof | |
| JP2009516658A (en) | 3,6-dihydro-2-oxo-6H-1,3,4-thiadiazine derivative | |
| Aghcheli et al. | Design, synthesis, and biological evaluation of 1-(5-(benzylthio)-1, 3, 4-thiadiazol-2-yl)-3-phenylurea derivatives as anticancer agents | |
| CN106674136A (en) | Anti-tumor pyrimidine compounds and preparation method thereof | |
| CN106749097B (en) | A kind of chloro- 2- aminobenzothiazole analog derivative of 6- and its preparation method and application | |
| ES2804304T3 (en) | Hepatic X receptor (LXR) modulators | |
| CN102304091A (en) | Emodin and fluorouracil combined compound having antitumor activity and preparation method thereof | |
| Kolluri et al. | Design, synthesis of novel (Z)-2-(3-(4-((3-benzyl-2, 4-dioxothiazolidin-5-ylidene) methyl)-1-phenyl-1H-pyrazol-3-yl) phenoxy)-N-arylacetamide derivatives: Evaluation of cytotoxic activity and molecular docking studies | |
| CN103980252A (en) | 1, 2, 4-triazole-contained triazole Schiff base drug for treating tumor | |
| CN102850337B (en) | Multi-azole linked spirorenone compound and preparation method and application thereof | |
| JP5701387B2 (en) | Dicarboximide derivative of berbamine, its preparation method and use | |
| B Palkar et al. | Novel series of coumarinyl substituted-thiazolidin-2, 4-dione analogs as anticancer agents: design, synthesis, spectral studies and cytotoxicity evaluation | |
| Ayyad et al. | Anti-Inflammatory, Proton Pump Inhibitor and Synthesis of Some New Benzimidazole Derivatives | |
| CN112047941B (en) | Compound and application thereof in preparing medicine for treating diseases caused by high expression of Flt3/c-Met kinase | |
| CN108148053A (en) | Sulfanilamide (SN) triazole Tubulin polymerization inhibitors and its synthetic method and application | |
| CN102216280B (en) | Bisarylurea derivatives and their use | |
| CN105061430A (en) | Preparation method of anti-tumor compound and application of compound | |
| CN101402587B (en) | Substituted acethydrazide derivatives, preparation method and application thereof | |
| WO2015043487A1 (en) | Quinazoline compound, and preparation method 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 |
Granted publication date: 20120502 Termination date: 20150709 |
|
| EXPY | Termination of patent right or utility model |