CN108947858A - A kind of preparation method and application of chalcone, dihydrochalcone and chromocor compound - Google Patents
A kind of preparation method and application of chalcone, dihydrochalcone and chromocor compound Download PDFInfo
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Abstract
The invention discloses the preparation method and applications of a kind of chalcone, dihydrochalcone and chromocor compound, the 3 of synthetic method synthesis through the invention, 4 ', 6 '-trihydroxy -4- methoxyl group chalcones are stronger to the inhibitory effect of a- glucuroide, can be used for reducing postprandial hyperglycemia；4- dimethylamino chalcone, 4-HC, 3- hydroxyl -4- methoxyl group chalcone and 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones are obvious to the inhibitory effect of non-glycosylation, can be used for the treatment to diabetes, atherosclerosis.
Description
Technical field
The present invention relates to chalcone compounds technology of preparing, specifically a kind of chalcone, dihydrochalcone and flavones
Close the preparation method and application of object.
Background technique
Diabetes be due to the hormone of internal insulin deficit or antagonism insulin increase or insulin in target cell not
Can bring into normal play a kind of syndrome of glucose, protein caused by physiological action and disorders of lipid metabolism.Traditional mouth
Antidiabetic drug offer limited effectiveness is taken, the basic research of new natural diabetes medicament has been emergency task too impatient to wait.With
The further investigation to Diabetes Foundation theory, the antidiabetic medicine of a variety of mechanism of action have been used for clinical evaluation and treatment,
Wherein Insulin secretagogues cause extensive concern.
Chalcone and its derivative are the products that cross aldol condensation occurs for aromatic aldehyde ketone, are a variety of native compounds of synthesis
Important organic synthesis intermediate.The chemical structure of chalcone is 1,3- diphenylprop ketenes, using it as the natural compounds of parent
Object is present in the plants such as Radix Glycyrrhizae, safflower, these natural normal phenolic hydroxy groups of chalcone.Due to chalcone molecular structure flexibility compared with
Greatly, can be in conjunction with different receptors, therefore there is extensive bioactivity, such as antitumor, inhibition and scavenging activated oxygen resist
Bacterium, antiallergy, antiviral, antiulcer and spasmolysis etc..The classical synthetic method of chalcone is using highly basic or strong acid catalyst benzene second
The aldol condensation of ketone and its derivative and aromatic aldehyde, yield 10% ~ 70%.In recent years, various catalyst constantly discover and to anti-
A large amount of explorations of condition are answered, the synthetic method of chalcone has been intended to diversification.
Summary of the invention
The purpose of the present invention is to provide the preparation method of a kind of chalcone, dihydrochalcone and chromocor compound and answer
With to solve the problems mentioned in the above background technology.
To achieve the above object, the invention provides the following technical scheme:
1. chalcone: the synthesis of 4- dimethylamino chalcone, comprising the following steps:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 4- dimethylamino chalcone: 2,4-dihydroxyacetophenone (0.02mol) is dissolved in 10ml dehydrated alcohol, stirring
Lower addition 10%NaOH 20ml keeps reaction temperature < 10 DEG C, the 20ml of (0.02mol) paradime thylaminobenzaldehyde is added dropwise
Ethanol solution then heats to 25 DEG C of reactions；After complete reaction, reactant is poured into ice water, it is heavy orange colour occurs
It forms sediment, filters, washed respectively with water and dehydrated alcohol.
2. the synthesis of 4-HC, comprising the following steps:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 4-HC: 2,4-dihydroxyacetophenone 2.4g(0.02mol) it is dissolved in 20ml dehydrated alcohol, by it
It is slowly added dropwise in 10% ice-cold NaOH solution, the 10ml dehydrated alcohol that 4- hydroxy benzaldehyde is then added dropwise at the same rate is molten
Liquid is warming up to 25 DEG C and is stirred to react, stands after complete reaction, filters, is washed at least twice with ice-cold dehydrated alcohol.
3. dihydrochalcone: the synthesis of 3- hydroxyl -4- methoxyl group chalcone, comprising the following steps:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 3- hydroxyl -4- methoxyl group chalcone: 2,4-dihydroxyacetophenone (0.014mol) is dissolved in 10ml dehydrated alcohol
In, it is added with stirring 10% NaOH 5ml, reaction temperature < 10 DEG C is kept to be slowly added dropwise after about 20min is sufficiently stirred
The 10ml ethanol solution of (0.014mol) vanillic aldehyde then heats to 25 DEG C of reactions, after complete reaction, filters, filter residue
For lightpink, washed at least twice with ice-cold dehydrated alcohol.
4. flavone compound: the synthesis of 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones, comprising the following steps:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones: 2,4-dihydroxyacetophenone (0.014mol) is dissolved in
In 25ml dehydrated alcohol, 50% KOH of 5ml is instilled dropwise, vanillic aldehyde (0.014mol) then is added on a small quantity in batches, at 30 DEG C
It is stirred to react, is detected with TLC to fully reacting；Reactant is poured into trash ice, with 1M HCl tune pH value to 2, stands, uses
CH2Cl2 extraction, organic layer are washed after merging, and rotary evaporation boils off solvent.
As a further solution of the present invention: the synthetic method of 2,4-dihydroxyacetophenone are as follows: by anhydrous zinc chloride and second
4 molecular sieves are added in acid after mixing, are slowly added to (0.1mol) finely ground resorcinol on a small quantity in batches, next time at 100 DEG C
Stream reaction 5h, is poured into 120ml trash ice after reactant is cooled to room temperature, and product crystallization is precipitated, and filters, washs two with ice water
It is secondary.
Above-mentioned 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcone is used to prepare the application for reducing postprandial hyperglycemia drug.
Above-mentioned 4- dimethylamino chalcone, 4-HC, 3- hydroxyl -4- methoxyl group chalcone and 3,4 ', 6 '-three hydroxyls
Base -4- methoxyl group chalcone is used to prepare the application for the treatment of diabetes, atherosclerosis drug.
Compared with prior art, the beneficial effects of the present invention are: 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones are to the Portugal a-
The inhibitory effect of polyglycoside enzyme is stronger, can be used for reducing postprandial hyperglycemia；4- dimethylamino chalcone, 4-HC, 3-
Hydroxyl -4- methoxyl group chalcone and 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones compare the inhibitory effect of non-glycosylation
It is more apparent, it can be used for the treatment to diabetes, atherosclerosis.
Detailed description of the invention
Fig. 1 is the chromatogram of the inhibitory effect of 1 ~ 4 pair of alpha-glucosidase of chalcone.
Fig. 2 is the chromatogram of the inhibitory effect of 1 ~ 4 pair of protein non-enzyme glycosylation of chalcone.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
Embodiment one,
A, the synthesis of 2,4-dihydroxyacetophenone: being added 4 molecular sieves for anhydrous zinc chloride and acetic acid after mixing, in batches few
Amount is slowly added to (0.1mol) finely ground resorcinol, and the back flow reaction 5h at 100 DEG C is poured into after reactant is cooled to room temperature
In 120ml trash ice, product crystallization is precipitated, and is filtered, is washed twice with ice water, obtain crude product.
B, the synthesis of 4- dimethylamino chalcone 1: 2,4-dihydroxyacetophenone (0.02mol) is dissolved in 10ml dehydrated alcohol
In, it is added with stirring 10%NaOH 20ml, keeps reaction temperature < 10 DEG C.(0.02mol) paradime thylaminobenzaldehyde is added dropwise
20ml ethanol solution, then heat to 25 DEG C of reactions；After complete reaction, reactant is poured into ice water, tangerine occurs
Yellow mercury oxide is filtered, is washed respectively with water and dehydrated alcohol.Yield 76.3%, 108-110 DEG C of fusing point.Spectral data: MS:m/z=
252 (M+1, 100%).IR:3433cm-1,1614cm-1.1HNMR: δ=3.04(s, 6H, NMe2), 6.72(d, 2H, H3,
), H5 7.34(d, 1H, H α), 7.47(d, 2H, H2, H6), 7.54(m, 3H, H3 ' and, H4 ', H5 '), 7.79(d, 1H, H β), 8.00
(d, 2H, H2 ', H6 ').
Embodiment two,
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 4-HC 2: 2,4-dihydroxyacetophenone 2.4g(0.02mol) it is dissolved in 20ml dehydrated alcohol, it will
It is slowly added dropwise in 10% ice-cold NaOH solution, and the 10ml that 2.4g 4- hydroxy benzaldehyde is then added dropwise at the same rate is anhydrous
Ethanol solution is warming up to 25 DEG C and is stirred to react.It stands after complete reaction, filters, wash two ~ tri- with ice-cold dehydrated alcohol
It is secondary, yield 10%, 328 DEG C of fusing point.Spectral data: MS:m/z=121 (100%).IR:3433cm-1,1614cm-1.1H
NMR: δ=6.92(d, 2H, H3, H5), 7.26(m, 3H, H3 ', H4 ', H5 '), 7.50(d, 1H, H α), 7.59(d, 1H, H
β), 7.98(m, 2H, H2, H6), 8.20(d, 2H, H2 ', H6 ') and, 9.85(s, 1H, OH).
Embodiment three,
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 3- hydroxyl -4- methoxyl group chalcone 3: 2,4-dihydroxyacetophenone 1.68g(0.014mol) be dissolved in 10ml without
In water-ethanol, it is added with stirring 10% NaOH 5ml, keeps reaction temperature < 10 DEG C.After about 20min is sufficiently stirred, it is slowly added dropwise
2.13g(0.014mol) the 10ml ethanol solution of vanillic aldehyde then heats to 25 DEG C of reactions.After complete reaction, it filters,
Filter residue is lightpink, two are washed with ice-cold dehydrated alcohol ~ three times.Yield 5.1%.Spectral data: MS:m/z=151 (
100%).IR:3433cm-1,1659cm-1.1H NMR: δ=3.74(s, 3H, OCH3), 6.50 ~ 6.51(m, 3H,
), ArH 7.22(d, 1H, CH), 7.30 ~ 7.40(m, 4H, ArH), 9.27(s, 1H, OH).
Example IV,
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones 4: 2,4-dihydroxyacetophenone (0.014mol) is dissolved
In 25ml dehydrated alcohol, 50% KOH of 5ml is instilled dropwise, vanillic aldehyde (0.014mol) then is added on a small quantity in batches, at 30 DEG C
Under be stirred to react, detected with TLC to fully reacting；Reactant is poured into trash ice, with 1M HCl tune pH value to 2, stands, uses
CH2Cl2 extraction, organic layer are washed after merging, and rotary evaporation boils off solvent, obtains yellow-brown solid powder 2.08g, yield
51.8%, 79-80 DEG C of fusing point.Spectral data: MS:m/z=151 (100%).IR:3433cm-1,1614cm-1.1H NMR: δ=
3.87(s, 3H, OCH3), 6.44 ~ 6.95(m, 3H, ArH), 7.43(d, 1H, CH) and, 7.85(m, 3H, ArH), 7.91(d,
1H, CH), 12.70(s, 1H, OH), 13.50(s, 1H, OH).
Respectively draw above-described embodiment in chalcone compounds solution (2mg/ml) and 50ul-glucuroide
In the phosphate buffer solution for the 0.05M that solution (3mg/5ml) is dissolved in pH=7.28, on JASCD J-810 circular dichroism spectrometer
Test, scanning range (180-300nm).Scanning result such as Fig. 1,2, the results show that 3,4 ', 6 '-trihydroxy -4- methoxyl group Cha Er
Ketone is stronger to the inhibitory effect of a- glucuroide, can be used for reducing postprandial hyperglycemia；4- dimethylamino chalcone, 4- hydroxyl are looked into
That ketone, 3- hydroxyl -4- methoxyl group chalcone and 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones imitate the inhibition of non-glycosylation
Fruit is obvious, can be used for the treatment to diabetes, atherosclerosis.
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie
In the case where without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive, and the scope of the present invention is by appended power
Benefit requires rather than above description limits, it is intended that all by what is fallen within the meaning and scope of the equivalent elements of the claims
Variation is included within the present invention.Any reference signs in the claims should not be construed as limiting the involved claims.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped
Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should
It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
The other embodiments being understood that.
Claims (10)
1. chalcone: the synthetic method of 4- dimethylamino chalcone, it is characterised in that: the following steps are included:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 4- dimethylamino chalcone: 2,4-dihydroxyacetophenone (0.02mol) is dissolved in 10ml dehydrated alcohol, stirring
Lower addition 10%NaOH 20ml keeps reaction temperature < 10 DEG C, the 20ml of (0.02mol) paradime thylaminobenzaldehyde is added dropwise
Ethanol solution then heats to 25 DEG C of reactions；After complete reaction, reactant is poured into ice water, it is heavy orange colour occurs
It forms sediment, filters, washed respectively with water and dehydrated alcohol.
2. chalcone: the synthetic method of 4-HC, it is characterised in that: the following steps are included:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 4-HC: 2,4-dihydroxyacetophenone 2.4g(0.02mol) it is dissolved in 20ml dehydrated alcohol, by it
It is slowly added dropwise in 10% ice-cold NaOH solution, the 10ml dehydrated alcohol that 4- hydroxy benzaldehyde is then added dropwise at the same rate is molten
Liquid is warming up to 25 DEG C and is stirred to react, stands after complete reaction, filters, is washed at least twice with ice-cold dehydrated alcohol.
3. dihydrochalcone: the synthetic method of 3- hydroxyl -4- methoxyl group chalcone, it is characterised in that: the following steps are included:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 3- hydroxyl -4- methoxyl group chalcone: 2,4-dihydroxyacetophenone (0.014mol) is dissolved in 10ml dehydrated alcohol
In, it is added with stirring 10% NaOH 5ml, reaction temperature < 10 DEG C is kept to be slowly added dropwise after about 20min is sufficiently stirred
The 10ml ethanol solution of (0.014mol) vanillic aldehyde then heats to 25 DEG C of reactions, after complete reaction, filters, filter residue
For lightpink, washed at least twice with ice-cold dehydrated alcohol.
4. flavone compound: the synthetic method of 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones, it is characterised in that: including with
Lower step:
A, the synthesis of 2,4-dihydroxyacetophenone；
B, the synthesis of 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones: 2,4-dihydroxyacetophenone (0.014mol) is dissolved in
In 25ml dehydrated alcohol, 50% KOH of 5ml is instilled dropwise, vanillic aldehyde (0.014mol) then is added on a small quantity in batches, at 30 DEG C
It is stirred to react, is detected with TLC to fully reacting；Reactant is poured into trash ice, with 1M HCl tune pH value to 2, stands, uses
CH2Cl2 extraction, organic layer are washed after merging, and rotary evaporation boils off solvent.
5. synthetic method according to claim 1 to 4, it is characterised in that: the synthetic method of 2,4-dihydroxyacetophenone
Are as follows: 4 molecular sieves are added in anhydrous zinc chloride and acetic acid after mixing, be slowly added on a small quantity in batches (0.1mol) it is finely ground between
Benzenediol, the back flow reaction 5h at 100 DEG C, is poured into 120ml trash ice after reactant is cooled to room temperature, and product crystallization is precipitated,
It filters, is washed twice with ice water.
6. 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones of synthetic method synthesis as claimed in claim 4 are used to prepare drop
The application of low postprandial hyperglycemia drug.
7. the 4- dimethylamino chalcone of synthetic method synthesis as described in claim 1 is used to prepare treatment diabetes, artery
The application of anti-atherosclerotic agent.
8. it is athero- that the 4-HC of synthetic method synthesis as claimed in claim 2 is used to prepare treatment diabetes, artery
Harden the application of drug.
9. the 3- hydroxyl -4- methoxyl group chalcone of synthetic method as claimed in claim 3 synthesis be used to prepare treatment diabetes,
The application of atherosclerosis drug.
10. synthetic method synthesis as claimed in claim 4 is used to prepare with 3,4 ', 6 '-trihydroxy -4- methoxyl group chalcones
The application for treating diabetes, atherosclerosis drug.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101208351A (en) * | 2005-06-24 | 2008-06-25 | 帝斯曼知识产权资产管理有限公司 | Compounds for the treatment of non-autoimmune type 2 diabetes mellitus and/or syndrome x |
| US20090252694A1 (en) * | 2006-04-03 | 2009-10-08 | Industry-Academic Cooperation Foundation Gyeongsang National Universtiy | Novel Chalcone Derivatives, Pharmaceutically Acceptable Salt, Method for Preparation and Uses Thereof |
| TW201306829A (en) * | 2011-08-10 | 2013-02-16 | Univ Kaohsiung Medical | Composition for treating atherosclerosis and a preparation method thereof |
| US20150374643A1 (en) * | 2014-06-25 | 2015-12-31 | Research & Business Foundation Sungkyunkwan University | Composition for inducing differentiation into beige and brown adipocytes and method of inducing the same |
| CN107501073A (en) * | 2017-08-12 | 2017-12-22 | 西北大学 | Primin derivative and its synthetic method and application |
-
2018
- 2018-08-22 CN CN201810957656.0A patent/CN108947858A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101208351A (en) * | 2005-06-24 | 2008-06-25 | 帝斯曼知识产权资产管理有限公司 | Compounds for the treatment of non-autoimmune type 2 diabetes mellitus and/or syndrome x |
| US20090252694A1 (en) * | 2006-04-03 | 2009-10-08 | Industry-Academic Cooperation Foundation Gyeongsang National Universtiy | Novel Chalcone Derivatives, Pharmaceutically Acceptable Salt, Method for Preparation and Uses Thereof |
| TW201306829A (en) * | 2011-08-10 | 2013-02-16 | Univ Kaohsiung Medical | Composition for treating atherosclerosis and a preparation method thereof |
| US20150374643A1 (en) * | 2014-06-25 | 2015-12-31 | Research & Business Foundation Sungkyunkwan University | Composition for inducing differentiation into beige and brown adipocytes and method of inducing the same |
| CN107501073A (en) * | 2017-08-12 | 2017-12-22 | 西北大学 | Primin derivative and its synthetic method and application |
Non-Patent Citations (3)
| Title |
|---|
| MAKARAND ATTARDE等: "Synthesis and evaluation of chalcone derivatives for its alpha amylase inhibitory activity", 《ORGANIC CHEMISTRY》 * |
| YUNSHENG XUE等: "A DFT study on the structure and radical scavenging activity of newly synthesized hydroxychalcones", 《J.PHYS.ORG.CHEM.》 * |
| 陈万木，郭宏雄: "环上取代基对苯乙酮和苯甲醛缩合反应的影响", 《合成化学》 * |
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