CN104003853A - Chalcone derivative and application thereof - Google Patents
Chalcone derivative and application thereof Download PDFInfo
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- CN104003853A CN104003853A CN201410149716.8A CN201410149716A CN104003853A CN 104003853 A CN104003853 A CN 104003853A CN 201410149716 A CN201410149716 A CN 201410149716A CN 104003853 A CN104003853 A CN 104003853A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Abstract
The invention discloses a chalcone derivative with good anti-free radical oxidative damage activity. The structural formula of the chalcone derivative is shown as the following. The preparation method of the chalcone derivative includes: letting syringaldehyde and para-substituted acetophenone react in piperidine and under a high temperature so as to generate corresponding substituted chalcone; reacting purified chalcone with sodium borohydride under a cerous chloride heptahydrate condition to generate a chalcone derivative crude product, and then conducting purification. , Compared with ascorbic acid, the product provided by the invention has low anti-DPPH free radical and anti-ABTS<+> free radical IC50 value, and strong free radical scavenging ability, thus having broad application prospects in preparing drugs for treating neurodegenerative diseases. (formula I).
Description
Technical field
The invention belongs to chemical field of medicaments, more specifically, relate to a kind of chalcone derivative with Green Tea Extract activity and preparation method thereof.
Background technology
Up-to-date census shows, present 60 years old above the elderly's quantity of China has 1.3 hundred million, and China has stepped into aging society in advance.Nerve degenerative diseases, as the elderly's healthy and quality of life in the disease serious harms such as senile dementia, parkinsonism and apoplexy.
The pathogenesis of these diseases still imperfectly understands at present, also without effective methods for the treatment of.But some researchs in recent years show, the active oxygen that oxidative stress produces and NO free radical are at the apoptosis of inducing cell and cause having brought into play vital role aspect nerve degenerative diseases.Cerebral tissue is the tissue that oxygen-consumption is the highest, metabolism is the most vigorous, and it relies on oxygen height, causes active oxygen to increase after radical damage, and tissue, in superoxidant state, easily gives rise to diseases, and comprises nerve degenerative diseases.Up to the present, only have a few medicine to can be used for some nerve degenerative diseases, and side effect is many.So it is an important directions of present field of medicaments that R and D have the medicine of removing free radical always.
That chalcone compounds has is antitumor, suppress and remove the multiple pharmacologically actives such as oxyradical, antibacterial, antiviral, parasiticide, anti-gastric-ulcer and antianaphylaxis.And the similar thing tool of the hydroxylated chalcone with phenol structure good anti-oxidant, remove the pharmacological actions such as free radical.Because nerve degenerative diseases may be because body active oxygen too much causes, so being used for the treatment of nerve degenerative diseases, chalcone derivative may have good effect.
Under such background, the present invention researches and develops out a kind of new chalcone derivative with good Green Tea Extract activity just.
Summary of the invention
The present invention overcomes the not high defect of existing nervus retrogression medicine Green Tea Extract activity, and a kind of chalcone derivative with good Green Tea Extract activity is provided.
Another object of the present invention is to provide a kind of method of preparing above-mentioned chalcone derivative.
A further object of the present invention is the above-mentioned chalcone derivative to be applied to prepare the application of the medicine of Green Tea Extract damage.
Chalcone derivative of the present invention, called after (E)-4-[3-hydroxyl-3-(4-substituting group phenyl)] propenyl-2,6-syringol, has the molecular structure of formula I:
Formula I
Wherein R base is alkyl or alkoxy or halogen atom.
Preferably, R base is methyl, methoxyl group or bromine.Most preferably, R base is methyl.As follows to the structural formula of these three kinds of preferred chalcone derivatives and title:
The preparation method of chalcone derivative of the present invention is also provided herein, has comprised the following steps:
S1. the preparation of cinnamophenone:
Reaction formula is as follows:
；
S2. the preparation of chalcone derivative:
Reaction formula is as follows:
。
The application of a kind of above-mentioned chalcone derivative in preparation treatment nerve degenerative diseases medicine is provided according to demand again.
Described nervus retrogression is alzheimer's disease, epilepsy or Parkinson's disease.
Beneficial effect of the present invention is, the ability that described chalcone derivative is removed free radical is stronger, aspect preparation treatment nerve degenerative diseases medicine, having broad application prospects.
Embodiment
Below in conjunction with specific embodiment, further explain the present invention, but embodiment does not limit in any form to the present invention.Unless stated otherwise, the present invention adopts test method, reagent and equipment are the art ordinary method, reagent and equipment.
Embodiment 1 (E)-4-[3-hydroxyl-3-(4-bromophenyl)] propenyl-2, the preparation of 6-syringol (10b)
10b
In 50 mL pear shape bottles, add 1.82g syringic aldehyde, 1.99g 4-bromoacetophenone and 1mL piperidines, be placed in rapidly 160 ℃ of oil baths, stirs lower backflow 1h, obtains scarlet thick liquid.Reaction process is followed the tracks of with TLC.Be cooled to after room temperature, under ice bath and violent stirring, add extremely dense NaOH solution, more than regulating pH to 12.To be acidified to pH be 1～2 to enriching HCl again.Add a large amount of distilled water, violent stirring, obtains yellow turbid solution and orange red oily matter again.Continue to stir, the orange red yellow that gradually becomes, standing, there are a large amount of yellow solids to generate.Low temperature is long placed in again, all becomes yellow until orange red, filters, and adds appropriate cold dehydrated alcohol to wash away variegated, then rinses with large water gaging, obtains 3,5-dimethoxy-4 '-hydroxyl-4 '-bromine cinnamophenone crude product.With acetone, add water recrystallization, obtain yellow crystals 3,5-dimethoxy-4 '-hydroxyl-4 '-bromine cinnamophenone sterling.
Take 0.91g 3,5-dimethoxy-4 '-hydroxyl-4 '-bromine cinnamophenone dissolves in 20mL tetrahydrofuran (THF), add 3mL methyl alcohol and 1g seven water cerous compoundss, stir, under ice bath, gradation adds 0.12g sodium borohydride, control adds the speed of sodium borohydride, reaction 30min, and reaction process is followed the tracks of with TLC.After having reacted, add a large amount of distilled water termination reactions, mixed solution is extracted with ethyl acetate, collect ethyl acetate layer, evaporate to dryness ethyl acetate, obtaining white solid, is chalcone derivative crude product, by ethyl acetate, adds sherwood oil recrystallization purifying, obtain end product (E)-4-[3-hydroxyl-3-(4-bromophenyl)] propenyl-2,6-syringol (10b).The new compound 10b of synthesized by IR,
1hNMR confirms structure.
White?powder,?mp?136.5-136.8?℃.IR?(KBr,?cm
-1):3456,?3188,?1602,?1513,?1212.?
1HNMR?(400?MHz,?DMSO)?δ8.36?(s,?1H),?7.53?(d,?J=?8.2?Hz,?2H),?7.34?(d,?J=?8.2?Hz,?2H),?6.68?(s,?2H),?6.48?(d,?J=?15.7?Hz,?1H),?6.21?(dd,?J=?15.7,?6.5?Hz,?1H),?5.63?(d,?J=?4.0?Hz,?1H),?5.24-5.14?(m,?1H),?3.75?(s,?6H).
Embodiment 2 (E)-4-[3-hydroxyl-3-(4-aminomethyl phenyl)] propenyl-2, the preparation of 6-syringol (11b)
11b
In 50 mL pear shape bottles, add 1.82g syringic aldehyde, 1.34g 4-methyl acetophenone and 1mL piperidines, be placed in rapidly 160 ℃ of oil baths, stirs lower backflow 1h, obtains scarlet thick liquid.Add respectively 2-3mL dehydrated alcohol and distilled water, continue reaction 20min.Reaction process is followed the tracks of with TLC.Reacted and be cooled to after room temperature, pour beaker into, separately add 10-15mL distilled water, stir, in ice bath downhill reaction liquid, add appropriate concentrated hydrochloric acid, limit edged stirs, regulate pH to 1-2, separately add a large amount of distilled water, obtain yellow turbid solution and orange red oily matter, continue to stir, the orange red yellow that gradually becomes, continues in ice bath to stir, and has a large amount of faint yellow solids to generate, be stirred to orange red all become faint yellow, filter, a small amount of cold dehydrated alcohol washes away variegated, separately with large water gaging, rinses, obtain 3,5-dimethoxy-4 '-hydroxyl-4 '-methyl cinnamophenone crude product.With acetone, add water recrystallization, obtain light yellow crystal 3,5-dimethoxy-4 '-hydroxyl-4 '-methyl cinnamophenone sterling.
Take 0.75g 3,5-dimethoxy-4 '-hydroxyl-4 '-methyl cinnamophenone dissolves in 20mL tetrahydrofuran (THF).Add 3mL methyl alcohol and 1g seven water cerous compoundss, stir, under ice bath, gradation adds 0.12g sodium borohydride, controls the speed and the reacting liquid temperature that add sodium borohydride, stirring reaction 30min under ice bath, and reaction process is followed the tracks of with TLC.After having reacted, add a large amount of distilled water termination reactions, mixed solution is extracted with ethyl acetate, collect ethyl acetate layer, evaporate to dryness ethyl acetate, obtaining white solid, is chalcone derivative crude product, by ethyl acetate, adds sherwood oil recrystallization purifying, obtain (E)-4-[3-hydroxyl-3-(4-aminomethyl phenyl)] propenyl-2,6-syringol (11b).The new compound 11b of synthesized by by IR,
1hNMR confirms structure.White?needle?crystal,?mp?128.5-129.6?℃.IR?(KBr,?cm
-1):3456,?3188,?1602,?1513,?1212.?
1HNMR?(400?MHz,?DMSO)?δ?8.36?(s,?1H),?7.26?(d,?J=?8.0?Hz,?2H),?7.14?(d,?J=?7.9?Hz,?2H),?6.66?(s,?2H),?6.45?(d,?J=?15.6?Hz,?1H),?6.21?(dd,?J=?15.8,?6.5?Hz,?1H),?5.45?(d,?J=?4.1?Hz,?1H),?5.19?-?5.12?(m,?1H),?3.75?(s,?6H),?2.28?(s,?3H).
Embodiment 3 (E)-4-[3-hydroxyl-3-(4-p-methoxy-phenyl)] propenyl-2, the preparation of 6-syringol (13b)
13b
In 50 mL pear shape bottles, add 1.82g syringic aldehyde, 1.50g 4-methoxyacetophenone and 1mL piperidines, be placed in rapidly 160 ℃ of oil baths, stirs lower backflow 1h, obtains scarlet thick liquid.Add 2-3mL dehydrated alcohol, continue reaction 20min.Reaction process is followed the tracks of with TLC.Reacted and be cooled to room temperature, under ice bath and intensively stirred condition, reaction solution has been poured in a large amount of cold dilute hydrochloric acid solution, then added a large amount of distilled water, obtained yellow turbid solution and orange red oily matter.Continue to stir the orange red yellow that gradually becomes.In ice bath, continue to stir, have a large amount of khaki color solids to generate.Be stirred to the orange red khaki color that all becomes, filter.Add a small amount of cold dehydrated alcohol to wash away variegated, then rinse with large water gaging, obtain 3,5-dimethoxy-4 '-hydroxyl-4 '-methoxyl group cinnamophenone crude product.With acetone, add water recrystallization, obtain yellow crystals 3,5-dimethoxy-4 '-hydroxyl-4 '-methoxyl group cinnamophenone sterling.
Take 0.81g 3,5-dimethoxy-4 '-hydroxyl-4 '-methyl cinnamophenone dissolves in 20mL tetrahydrofuran (THF).Add 3mL methyl alcohol and 1g seven water cerous compoundss, stir, under ice bath, gradation adds 0.12g sodium borohydride, strict speed and the reacting liquid temperature that adds sodium borohydride, the stirring reaction 30min under ice bath of controlling.Reaction process is followed the tracks of with TLC.After having reacted, add a large amount of distilled water termination reactions, mixed solution is extracted with ethyl acetate, and collects ethyl acetate layer.Evaporate to dryness ethyl acetate, obtains white solid, is chalcone derivative crude product.By ethyl acetate, add sherwood oil recrystallization purifying, obtain (E)-4-[3-hydroxyl-3-(4-p-methoxy-phenyl)] propenyl-2,6-syringol (13b).The new compound 13b of synthesized by by IR,
1hNMR confirms structure.White?needle?crystal,?mp?118.5-119.3?℃.IR?(KBr,?cm
-1):3461,?3229,?1602,?1516,?1251,?1200.?
1HNMR?(300?MHz,?DMSO)?δ8.37?(s,?1H),?7.29?(d,?J=?8.4?Hz,?2H),?6.89?(d,?J=?8.7?Hz,?2H),?6.67?(s,?2H),?6.44?(d,?J=?15.7?Hz,?1H),?6.22?(dd,?J=?15.8,?6.3?Hz,?1H),?5.43?(d,?J=?4.1?Hz,?1H),?5.23?-?5.06?(m,?1H),?3.75?(s,?6H),?3.73?(s,?3H).
Embodiment 4 11b, 13b and 10b remove DPPH, ABTS
+the ability of free radical is measured
Will
11bbe formulated as the solution of 8mmol/L, carry out gradient dilution and become concentration to be respectively the solution of 4mmol/L, 2mmol/L, 1mmol/L, 0.5mmol/L, 0.25mmol/L, 0.125mmol/L, 0.0625mmol/L, 0.03125mmol/L.
The solution of above-mentioned each concentration is added to respectively in DPPH solution, and the feature purple of DPPH solution shoals, and at 517nm place, has maximum absorption.According to the variation of absorbancy, can record
11bremove the IC of DPPH free radical
50value is 15.59 μ mol/L.
The solution of above-mentioned each concentration is added to respectively to ABTS
+in solution, ABTS
+the feature green of solution shoals or disappears, and measures absorbancy at 734nm place.According to the variation of absorbancy, record
11bremove ABTS
+the IC of free radical
50value is 9.37 μ mol/L.ABTS
+solution is by ABTS and K
2s
2o
8solution mixes 12-16h and prepares under the condition of room temperature lucifuge.
As stated above, measure 10b and 13b and remove DPPH, ABTS
+the ability of free radical.
10b, 11b and 13b remove DPPH free radical or ABTS
+the ability comparing result of the ability of free radical and xitix is as following table:
Result shows, the present invention thinks that three new compound 10b, 11b of protection are suitable with ability and xitix that 13b removes DPPH free radical, removing ABTS
+the ability of free radical is obviously better than xitix.
Claims (4)
1. a new chalcone derivative, is characterized in that, its molecular structure is suc as formula I:
Formula I
Wherein, substituent R is alkyl, alkoxy or halogen.
2. chalcone derivative according to claim 1, is characterized in that, substituent R is methyl, methoxyl group or bromine.
3. a chalcone derivative according to claim 1 is treated the application in nerve degenerative diseases medicine in preparation.
4. application according to claim 3, is characterized in that, described nervus retrogression is alzheimer's disease, epilepsy or Parkinson's disease.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104225583A (en) * | 2014-09-03 | 2014-12-24 | 苏州瑞派尔生物科技有限公司 | Composition for skin damage repair |
| CN105481715A (en) * | 2015-12-24 | 2016-04-13 | 陕西师范大学 | Camphor Schiff base, and preparation method and application thereof |
| CN106496052A (en) * | 2016-10-19 | 2017-03-15 | 汕头大学医学院 | Your ketone compounds a kind of and its preparation method and application |
| CN106619586A (en) * | 2016-12-26 | 2017-05-10 | 温州医科大学 | Application of L6H3 in preparation of drugs for treating Parkinson's disease and the like |
| CN108484511A (en) * | 2018-05-03 | 2018-09-04 | 山东大学 | A kind of ligustrazine chalcone compounds and its preparation method and application |
| CN110655464A (en) * | 2019-10-22 | 2020-01-07 | 肇庆学院 | Chalcone compound with oxyacetic acid structure and application thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104225583A (en) * | 2014-09-03 | 2014-12-24 | 苏州瑞派尔生物科技有限公司 | Composition for skin damage repair |
| CN104225583B (en) * | 2014-09-03 | 2016-09-28 | 苏州瑞派尔生物科技有限公司 | A kind of compositions repaired for skin injury |
| CN105481715A (en) * | 2015-12-24 | 2016-04-13 | 陕西师范大学 | Camphor Schiff base, and preparation method and application thereof |
| CN106496052A (en) * | 2016-10-19 | 2017-03-15 | 汕头大学医学院 | Your ketone compounds a kind of and its preparation method and application |
| CN106619586A (en) * | 2016-12-26 | 2017-05-10 | 温州医科大学 | Application of L6H3 in preparation of drugs for treating Parkinson's disease and the like |
| CN106619586B (en) * | 2016-12-26 | 2017-10-31 | 温州医科大学 | L6H3 prepares the application of anti-parkinson drug etc. |
| CN108484511A (en) * | 2018-05-03 | 2018-09-04 | 山东大学 | A kind of ligustrazine chalcone compounds and its preparation method and application |
| CN110655464A (en) * | 2019-10-22 | 2020-01-07 | 肇庆学院 | Chalcone compound with oxyacetic acid structure and application thereof |
| CN110655464B (en) * | 2019-10-22 | 2022-10-21 | 肇庆学院 | Chalcone compound with oxyacetic acid structure and application thereof |
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