CN108774187A - A kind of benzoxazole derivative preparation method and application - Google Patents
A kind of benzoxazole derivative preparation method and application Download PDFInfo
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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Abstract
The present invention provides a kind of benzoxazole derivative preparation method and application, the benzoxazole derivative is 5- Jia base benzoxazole -2- phenyl-benzamides, and structural formula is as follows：Benzoxazole derivative of the present invention can inhibit the growth of saccharomycete, and it can significantly reduce SOD, Cu-Zn-SOD, MDA, CAT and albumen concentration in drosophila body, due to obviously inhibiting the SIR2 of saccharomycete, it is most likely that inhibit the growth of cancer cell as SIRT1 inhibitor and enhance the oxidation resistance of drosophila.
Description
Technical field
The invention belongs to biomedicine technical fields, more particularly, to a kind of benzoxazole derivative preparation method and answer
With.
Background technology
Cancer is the principal disease burden in the whole world, and new case 11,000,000 about occurs every year；The most common pathogenesis of cancer in the whole world
For lung cancer, breast cancer and colorectal cancer, most common cancer mortality is lung cancer, gastric cancer and liver cancer.Cancer in China morbidity accounts for the whole world
20.3%, annual new cases are more than 2,200,000, and most common cancer male is：Lung cancer, gastric cancer, liver cancer, the cancer of the esophagus, women
For：Breast cancer, the cancer of the esophagus, gastric cancer, lung cancer, liver cancer, cervical carcinoma.Global pathogenesis of cancer is totally in rising trend, significantly rises
Cancer has lung cancer, breast cancer, colorectal cancer；The cancer being remarkably decreased has gastric cancer, cervical carcinoma.The Major Risk Factors of cancer include
Tobacco, alcohol, virus and infection, radiation and radiation, diet and nutrition, environmental exposure, genetic predisposition etc..Tobacco and alcohol disappear
Influence of the increase and modern way of life of expense for lung cancer, alimentary tract cancer, breast cancer is aggravating, diet and nutritive water
Flat raising results in the decline of gastric cancer and cancer of the esophagus.Therefore, target is acted on by the new albumen of synthesizing new compound and discovery
It is current effective important method to select and find new safely and effectively anticancer drug.
Sirtuin protein families are a kind of protease guarded very much during evolution.It is found first in the family
And the Sir2 albumen for the yeast studied, research have shown that Sirt2 is considered as being directly connected to biological metabolism state and the key in service life point
Son.And the homology highest of SIRT1 and Sir2 in mammals.SIRT1 wide expressions in mammalian tissues,
SIRT1 activity and expression by cancer suppressorfactor-tumour hyper-methylation gene 1 (HIC1), breast cancer deficiency factor 1 (DBC1) with
And the inhibition of E2F1 etc..Inhibit SIRT1 can inducing tumor cell growth retardation, and promote in the case where not influencing normal cell
Apoptosis of tumor cells.Therefore, SIRT1 may be a kind of potential antitumor drug target spot.
Benzooxazole kind compound has many unique chemical and physical features, has other compounds irreplaceable
Effect is widely used in pharmacy, material, fluorescent brightening etc..Benzooxazole kind compound is that a kind of important medicine is intermediate
Body, this kind of compound have the multiple biological activities such as anti-inflammatory, anti-oxidant, antibacterial, antitumor.
Invention content
In view of this, the present invention is directed to propose a kind of benzoxazole derivative preparation method and application, the benzoxazole
Derivative can be applied to prepare anticancer drug candidate.
In order to achieve the above objectives, the technical proposal of the invention is realized in this way：
A kind of benzoxazole derivative, the benzoxazole derivative are 5- Jia base benzoxazole -2- phenyl-benzoyl
Amine, structural formula are as follows：
Above-mentioned benzoxazole derivative is in the application for preparing silent message regulatory factor Sir2 inhibitor.
Above-mentioned benzoxazole derivative is in the expression for preparing SOD, Cu-Zn-SOD, MDA, CAT and related gene in drosophila body
Adjusting control agent application.
Above-mentioned benzoxazole derivative is preparing mitigation, is improving, the application in prevention and treating cancer drug.
Further, the cancer is lung cancer, gastric cancer, liver cancer, the cancer of the esophagus, breast cancer, the cancer of the esophagus, gastric cancer, lung cancer, liver
Cancer, cervical carcinoma.
The preparation method of above-mentioned benzoxazole derivative, includes the following steps：
(1) 5- Jia base benzoxazole -2- phenyl -3 '-amine is prepared；
(2) 5- Jia base benzoxazole -2- phenyl-benzamides are prepared.
Further, the preparation method of step (1) 5- Jia base benzoxazole -2- phenyl-the 3 '-amine includes following step
Suddenly：
A, 4- methylanthranilics phenol, gavaculine are added into reaction vessel, then stirs evenly, is then placed in
Strength rotor, is eventually adding polyphosphoric acids, is placed in oil bath pan and is heated to reflux, and when beginning to warm up, setting temperature is 110 DEG C, is waited for
When rotor starts slowly to rotate very much, then slowly increase temperature to 180 DEG C, continue back flow reaction 5h, TLC thin layer control to react knot
Beam；
B, NaHCO is added into the aqueous solution of 10%NaOH3, uniform stirring makes it completely dissolved obtained mixed solution；
The aqueous solution of 400ml 10%NaOH is added in 1L beakers, 9g (10.7mmol) is then added
C, reaction solution slowly pouring into mixed solution while hot, ice cube, which is added, in the while of falling reaction solution reduces the temperature of system,
The PH of system is finally transferred to 8~9, precipitation is generated, is filtered with Buchner funnel, then obtained solid small cake is smashed to pieces, is put
Enter vacuum drying chamber to be dried.It is to be dried to finish, then dried solid powder is dissolved in ethyl acetate, it filters out insoluble
Object is evaporated ethyl acetate, using dry column-packing, crosses silica gel column separating purification, with the mixed system of ethyl acetate and petroleum ether into
Row elution, is concentrated under reduced pressure and removes solvent, obtain parent nucleus 5- Jia base benzoxazole -2- phenyl -3 '-amine.
Further, the 4- methylanthranilics phenol that is used in above-mentioned steps a, gavaculine, polyphosphoric acids rub
You are than being 91.7：100.9：32.5.
Further, NaHCO in above-mentioned steps b3Additive amount be aqueous solution addition per 400ml 10%NaOH
10.7mmol NaHCO3。
Further, the preparation method of step (2) the 5- Jia base benzoxazole -2- phenyl-benzamides includes as follows
Step：
Anhydrous acetonitrile, benzoic acid are added into reaction vessel, after stirring and dissolving, tolysulfonyl is added thereto successively
Chlorine, triethylamine, 4-dimethylaminopyridine after stirring 10min, are added 5- Jia base benzoxazole -2- phenyl -3 '-amine, stir evenly
Afterwards, back flow reaction 4h, TLC thin layer controls are reacted to terminating under the conditions of 40 DEG C, after reaction, it is heavy that white are generated in bottle
It forms sediment, filtering, TLC thin layer control filtrates, filtrate component is mostly raw material, and white precipitate, which is ploughed under vacuum drying chamber, to be dried, and is obtained
To white solid, as 5- Jia bases benzoxazole -2- phenyl-benzamides.
Further, the additive amount of the absolute ethyl alcohol is 20ml, the benzoic acid, paratoluensulfonyl chloride, triethylamine, 4-
The additive amount of dimethylamino naphthyridine is followed successively by 1.8mmol, 1.8mmol, 2.7mmol, 0.25mmol.
Compared with the existing technology, benzoxazole derivative preparation method of the present invention and application have following excellent
Gesture：
Benzoxazole derivative preparation method of the present invention and application are based on yeast SIR2 and mammal SIRT1
Very high homology, it was demonstrated that benzoxazole derivative can inhibit the growth of saccharomycete, inhibit its metabolism growth；And it can significantly reduce fruit
SOD, Cu-ZnSOD, MDA, CAT and albumen concentration, influence the expression of SIRT1 extremely related genes in fly body, hence it is evident that inhibit
SIRT1 can inhibit the growth of cancer cell as SIRT1 inhibitor.
Description of the drawings
Fig. 1 is the synthetic route schematic diagram of the compounds of this invention (5- Jia base benzoxazole -2- phenyl)-benzamide；
Fig. 2 is (5- Jia base benzoxazole -2- phenyl) -3 '-amine nuclear magnetic resonance spectroscopy analysis charts in the embodiment of the present invention 1；
Fig. 3 is compound 5- Jia base benzoxazole -2- phenyl-benzamide nuclear magnetic resonance spectroscopies in the embodiment of the present invention 1
Analysis chart；
Fig. 4 is the compounds of this invention 5- Jia bases benzoxazole -2- phenyl-benzamides to BY4743 Yeast Growth activity
Striograph；
Fig. 5 is the compounds of this invention 5- Jia bases benzoxazole -2- phenyl-benzamides to BY4743 Yeast Growth curves
The comparison figure of slope；
Fig. 6 is the compounds of this invention 5- first base benzoxazole -2- phenyl-benzamides to SOD, Cu-Zn- in drosophila body
SOD, CAT, MDA expression activitiy figure：
Fig. 6-1 is compound to the active influence diagrams of SOD in drosophila body；
Fig. 6-2 is compound to the active influence diagrams of Cu-Zn-SOD in drosophila body；
Fig. 6-3 is compound to the active influence diagrams of CAT in drosophila body；
Fig. 6-4 is compound to the active influence diagrams of MDA in drosophila body；
Fig. 7 is the compounds of this invention 5- first base benzoxazole -2- phenyl-benzamides to CAT, MTH, Cu- in drosophila body
The expression quantity of Zn-SOD, Mn-SOD gene mRNA compares figure；
Fig. 7-1 is compound to CAT gene mRNAs relative expression quantity influence diagram in drosophila body；
Fig. 7-2 is compound to MTH gene mRNAs relative expression quantity influence diagram in drosophila body
Fig. 7-3 is compound to Cu-Zn-SOD gene mRNAs relative expression quantity influence diagram in drosophila body
Fig. 7-4 is compound to Mn-SOD gene mRNAs relative expression quantity influence diagram in drosophila body.
Specific implementation mode
In addition to being defined, technical term used in following embodiment has universal with those skilled in the art of the invention
The identical meanings of understanding.Test reagent used in following embodiment is unless otherwise specified conventional biochemical reagent；It is described
Experimental method is unless otherwise specified conventional method.
With reference to embodiment and attached drawing, the present invention will be described in detail.
Embodiment 1：A kind of benzoxazole derivative and preparation method thereof, steps are as follows：
1,5- Jia base benzoxazole -2- phenyl -3 '-amine is prepared
100ml stand up reaction bottle is taken, 91.7mmol 4- methylanthranilics phenol, 100.9mmol m-aminophenyl first is added
Then acid is stirred evenly with glass bar, be then placed in strength rotor, is eventually adding 110g (32.5mmol) polyphosphoric acids, is placed in
It is heated to reflux in oil bath pan.When beginning to warm up, setting temperature is 110 DEG C, when rotor starts slowly to rotate very much, then is slowly increased
Temperature continues back flow reaction 5h, TLC thin layer control to reaction and terminates to 180 DEG C.
The aqueous solution of 400ml 10%NaOH is added in 1L beakers, 9g (10.7mmol) NaHCO3 is then added, uniformly
Stirring, makes it completely dissolved.Reaction solution is slowly poured into the solution of NaOH and NaHCO3 while hot, ice is added in the while of falling reaction solution
Block reduces the temperature of system, and the PH of system is finally transferred to 8~9, generate precipitation, filtered with Buchner funnel, then will obtain
Solid small cake is smashed to pieces, is put into vacuum drying chamber and is dried.It is to be dried to finish.Dried solid powder is dissolved in acetic acid again
Ethyl ester filters out insoluble matter, is evaporated ethyl acetate, using dry column-packing, silica gel column separating purification is crossed, with ethyl acetate and oil
The mixed system of ether is eluted, and is concentrated under reduced pressure and is removed solvent, obtains white solid (15.8g, yield 66.4%).
Interpretation of result：
Obtained finished product is subjected to nmr analysis, obtains Fig. 2, it is as a result as follows：
1H NMR (400MHz, CDCl3/TMS) δ：7.635,7.614 (d, J=8.4, HZ, 1H), 7.563,7.538 (d, J
=10.4, HZ, 2H), 7.444,7.423 (d, J=8.4HZ, 1H), 7.313-7.274 (t, J=8HZ, 1H), 7.160-7.137
(dd, J1=8.4HZ, J2=1.2H, 1H), 6.849-6.824 (dd, J1=8.4HZ, J2=1.2H, 1H), 3.843 (s, 2H),
2.482 (s, 3H).
The above result shows that products therefrom is 5- Jia base benzoxazole -2- phenyl -3 '-amine.
2, prepare compound 5- Jia bases benzoxazole -2- phenyl-benzamides
It takes the reaction bulb of 50ml, is added anhydrous acetonitrile 20mL, benzoic acid 1.8mmol, after good stirring and dissolving, successively to it
Middle addition 0.342g (1.8mmol) paratoluensulfonyl chloride (TSCI), 0.28g (2.7mmol) triethylamine, 0.03g (0.25mmol)
After well stirring 10min, 1.5mmol 5- Jia base benzoxazole -2- phenyl -3 '-amine is added in 4-dimethylaminopyridine (DMAP),
After stirring evenly, back flow reaction 4h, TLC thin layer controls are reacted to terminating under the conditions of 40 DEG C.After reaction, it is generated in bottle
White precipitate, filtering, TLC thin layer control filtrates, filtrate component is mostly raw material, and white precipitate is ploughed under vacuum drying chamber and is done
It is dry, obtain white solid, as 5- Jia bases benzoxazole -2- phenyl-benzamides.
Interpretation of result：
Nmr analysis is carried out, Fig. 3 is obtained, it is as a result as follows：
1H NMR (400MHz, CDCl3/TMS) δ：8.387 (s, 1H), 8.028-8.010 (m, 3H), 7.913,7.895
(d, J=4.2HZ, 2H), 7.541-7.505 (m, 5H), 7.455,7.435 (d, J=8.4HZ, 1H), 7.176-7.155 (d, J
=8.4HZ, 1H), 2.485 (s, 3H).Its structural formula is as follows：
Embodiment 2：Benzooxazole kind compound is on the active influence of yeast cell growth
Saccharomycete is measured using automatic microbe growth analysis instrument (Growth Curves USA, Piscataway, NI)
Growth activity is divided into 2 groups, respectively in 100 hole cellular boards：1. 297 μ LYPD culture mediums, 3 μ LYPD bacterium solutions, 0.3 μ LDMSO
Solution, as blank control group.2. the 5- Jia base Ben Bing Evil of 297 μ LYPD culture mediums, 3 μ LYPD bacterium solutions, 0.3 a concentration of 0.1M of μ L
Azoles -2- phenyl)-benzamide DMSO solution.It is the amount that every hole is added above, and carries out parallel laboratory test three times.Keep culture
Temperature is 30 DEG C, measures the OD values in each honeycomb hole, METHOD FOR CONTINUOUS DETERMINATION 23h at 600nm every 20min.
Interpretation of result：
Experimental result is as shown in figure 4, be added the BY1743 saccharomycete pair of 5- Jia base benzoxazole -2- phenyl-benzamides
Number growth period time retardation shows that 5- Jia base benzoxazole -2- phenyl-benzamides may have BY4743 saccharomycete inhibition to make
With.Fig. 5 is that the slope of saccharomycete exponential phase compares figure, hence it is evident that dosing yeast growth is slow, illustrates the compound to yeast
Growth has certain inhibiting effect.
Embodiment 3：Influence of the benzoazole compounds 5- Jia base benzoxazole -2- phenyl-benzamides to drosophila
1. the grouping of drosophila, forage compounding and processing method
2d age male insects drosophila 600 is taken respectively, and stochastic averagina is divided into 3 groups：1. blank group：Feeding basal feed.②
Empty oil group：Feeding is added with the basal feed of solvent (corn oil).3. administration group：Feed is administered in feeding, and (experimental drug is dissolved in
In corn oil).All experimental groups replace a fresh culture per 3d.
It manages for every group 10, often 20 drosophilas of pipe.Be placed in (25 ± 1) DEG C, relative humidity (50-60) % constant temperature and humidity incubator
After middle raising 30d, N is used2Anesthesia, is put into spare in -80 DEG C of refrigerators.Every group of 5 pipes take out drosophila, by 1:49 (mg/mL) plus physiology
Brine, 4 DEG C of holding, 2500r/min centrifugations 20min are homogenized, and supernatant is taken to measure enzymatic activity.
For configuring 750ml basal feeds, each group component, which is added, is：DEXTROSE ANHYDROUS 72g, corn flour 72g, dry ferment
Powder 10g, agar powder 6g, adds water to 750ml, dries in the air 2 minutes after cooked, and adding preservative agent (contains the 75% of 1% ethyl-para-hydroxybenzoate
Alcohol) 40ml.
Basal feed added with solvent：On the basis of basal feed, 0.05ml/ml corn oils are added.
Feed is administered：On the basis of basal feed, the laboratory sample for being dissolved in corn oil (0.05ml/ml) is added
(0.2mg/ml)。
2. on the active influences of SOD and Cu-Zn-SOD in drosophila body
SOD and Cu-Zn-SOD activity in drosophila body is measured respectively using corresponding reagent box.From table 1, Fig. 6-1 and Fig. 6-2
As it can be seen that SOD and Cu-Zn-SOD activity is less than empty oily group in drosophila body after being administered 30 days.
SOD and Cu-Zn-SOD activity in 1 drosophila body of table
| Group | SOD(U/mgprot) | Cu-Zn-SOD(U/mgprot) |
| Blank group | 477.86±27.86 | 197.72±95.71 |
| Empty oil group | 524.86±8.41 | 267.05±35.52 |
| Administration group | 466.87±42.22 | 227.90±33.93 |
3. on the active influences of CAT in drosophila body
The activity of CAT in drosophila body is measured using corresponding reagent box.As seen in table 2 and Fig. 6-3, drosophila body after administration 30 days
Interior CAT activity is less than empty oily control group.
The activity of CAT in 2 drosophila body of table
| Group | CAT(U/mgprot) |
| Blank group | 54.53±5.55 |
| Empty oil control group | 65.25±8.17 |
| Administration group | 59.58±12.14 |
4. on the active influences of MDA in drosophila body
The activity of MDA in drosophila body is measured using corresponding reagent box.As seen in table 3, Fig. 6-4, drosophila body after administration 30 days
Interior MDA activity is significantly lower than empty oily control group.
The activity of MDA in 3 drosophila body of table
| Group | MDA(U/mgprot) |
| Blank group | 7.34±0.78 |
| Empty oil control group | 8.69±0.45 |
| Administration group | 7.37±0.39 |
5. the influence pair drosophila gene expression
The drosophila of -80 DEG C of preservations is taken, every group takes five pipes, Trizol methods to extract mRNA, and reverse transcription obtains cDNA, and -80 DEG C spare.
It is horizontal that Real Time-PCR methods detect anti-oxidant mRNA expression of gene associated.Compare RT49 analysis drosophilas CAT, MTH, Cu-Zn-
The expression quantity of SOD, Mn-SOD gene mRNA.
As shown in Fig. 7 and 7-1 to 7-4, the results show that CAT and MTH gene expressions are obviously low in the drosophila body of administration group
In empty oily group；The expression quantity of Cu-Zn-SOD and Mn-SOD genes is apparently higher than empty oily group in the drosophila body of administration group.
To sum up, it can be seen that compound 5- Jia base benzoxazole -2- phenyl-benzamides can be applied to be believed as silence
In terms of ceasing regulatory factor inhibitor, it may further be studied as anticancer drug.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (10)
1. a kind of benzoxazole derivative, it is characterised in that：The benzoxazole derivative is 5- Jia base benzoxazole -2- benzene
Base-benzamide, structural formula are as follows：
2. benzoxazole derivative as described in claim 1 is in the application for preparing silent message regulatory factor Sir2 inhibitor.
3. benzoxazole derivative as described in claim 1 is preparing SOD, Cu-Zn-SOD, MDA, CAT and phase in drosophila body
The expression regulation agent application of correlation gene.
4. benzoxazole derivative as described in claim 1 is preparing mitigation, is improving, answering in prevention and treating cancer drug
With.
5. benzoxazole derivative according to claim 4 is preparing mitigation, is improving, in prevention and treating cancer drug
Using, it is characterised in that：The cancer be lung cancer, gastric cancer, liver cancer, the cancer of the esophagus, breast cancer, the cancer of the esophagus, gastric cancer, lung cancer, liver cancer,
Cervical carcinoma.
6. a kind of preparation method of benzoxazole derivative described in claim 1, it is characterised in that：Include the following steps：
(1) 5- Jia base benzoxazole -2- phenyl -3 '-amine is prepared；
(2) 5- Jia base benzoxazole -2- phenyl-benzamides are prepared.
7. the preparation method of benzoxazole derivative according to claim 6, it is characterised in that：Step (1) the 5- first
The preparation method of base benzoxazole -2- phenyl -3 '-amine includes the following steps：
A, 4- methylanthranilics phenol, gavaculine are added into reaction vessel, then stirs evenly, is then placed in strength
Rotor is eventually adding polyphosphoric acids, is placed in oil bath pan and is heated to reflux, and when beginning to warm up, setting temperature is 110 DEG C, waits for rotor
When starting slowly to rotate very much, then temperature is slowly increased to 180 DEG C, continue back flow reaction 5h, TLC thin layer control to reaction and terminate；
B, NaHCO is added into the aqueous solution of 10%NaOH3, uniform stirring makes it completely dissolved obtained mixed solution；
C, reaction solution is slowly poured into mixed solution while hot, ice cube, which is added, in the while of falling reaction solution reduces the temperature of system, finally
The PH of system is transferred to 8~9, precipitation is generated, is filtered with Buchner funnel, then smash obtained solid small cake to pieces, is put into true
Empty drying box is dried.It is to be dried to finish, then dried solid powder is dissolved in ethyl acetate, insoluble matter is filtered out, is steamed
Dry ethyl acetate is crossed silica gel column separating purification, is washed with the mixed system of ethyl acetate and petroleum ether using dry column-packing
It is de-, it is concentrated under reduced pressure and removes solvent, obtain parent nucleus 5- Jia base benzoxazole -2- phenyl -3 '-amine.
8. the preparation method of benzoxazole derivative according to claim 7, it is characterised in that：It is used in the step a
4- methylanthranilics phenol, gavaculine, polyphosphoric acids molar ratio be 91.7：100.9：32.5；In the step b
NaHCO3Additive amount be NaHCO that aqueous solution per 400ml 10%NaOH adds 10.7mmol3。
9. the preparation method of benzoxazole derivative according to claim 6, it is characterised in that：Step (2) the 5- first
The preparation method of base benzoxazole -2- phenyl-benzamides includes the following steps：
Anhydrous acetonitrile, benzoic acid are added into reaction vessel, after stirring and dissolving, paratoluensulfonyl chloride, three are added thereto successively
After stirring 10min, 5- Jia base benzoxazole -2- phenyl -3 '-amine is added in ethamine, 4-dimethylaminopyridine, after stirring evenly,
Back flow reaction 4h under the conditions of 40 DEG C, TLC thin layer controls are reacted to terminating, and after reaction, white precipitate, mistake are generated in bottle
Filter, TLC thin layer control filtrates, filtrate component is mostly raw material, and white precipitate, which is ploughed under vacuum drying chamber, to be dried, and white is obtained
Solid, as 5- Jia bases benzoxazole -2- phenyl-benzamides.
10. the preparation method of benzoxazole derivative according to claim 9, it is characterised in that：The absolute ethyl alcohol
Additive amount is 20ml, the benzoic acid, paratoluensulfonyl chloride, triethylamine, 4-dimethylaminopyridine additive amount be followed successively by
1.8mmol、1.8mmol、2.7mmol、0.25mmol。
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145738A (en) * | 2005-08-04 | 2013-06-12 | 西特里斯药业公司 | Imidazo [2,1-b] thiayole derivatives as SIRTUIN modulating compounds |
| CN104016935A (en) * | 2014-05-07 | 2014-09-03 | 天津科技大学 | Benzoxazole derivative as well as preparation method and application thereof |
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2018
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145738A (en) * | 2005-08-04 | 2013-06-12 | 西特里斯药业公司 | Imidazo [2,1-b] thiayole derivatives as SIRTUIN modulating compounds |
| CN104016935A (en) * | 2014-05-07 | 2014-09-03 | 天津科技大学 | Benzoxazole derivative as well as preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 无: "CAS：328116-54-7", 《STN REGISTRY》 * |
| 曹祥荣主编: "《细胞生物学精要》", 31 December 2010 * |
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