CN107629040A - A kind of flavanone alcohols compound of the heteroaromatic containing N and its preparation method and application - Google Patents
A kind of flavanone alcohols compound of the heteroaromatic containing N and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of flavanone alcohols compound of heteroaromatic containing N to have following structure：Wherein Ar substituents are in Formulas I
Description
Technical field
The present invention relates to flavanone alcohols compound of a kind of heteroaromatic containing N and preparation method thereof anti-inflammatory is being prepared with it
Application in medicine.
Background technology
Inflammatory reaction is that body tackles internal external stimulus and a kind of caused defense reaction, clinic be usually expressed as it is red and swollen,
The signs such as hot pain and dysfunction.In most cases, inflammation is beneficial that this is the automatic defense reaction of human body.In inflammation
During disease, one side inflammatory factor can be damaged directly or indirectly to tissue and cell；On the other hand due to inflammation
It is congested and ooze out reaction, cause damage factor to be diluted, kill and surround；Make impaired group by essence and interstitial cell simultaneously
Knit and be regenerated and heal.It can be said that inflammation is the RUP of damage and antibody Monoclonal.The anti-inflammatory clinically used at present
Medicine includes NSAIDs, steroidal anti-inflammatory medicine, immunosuppressive drug etc., and these medicines are sent out in the treatment of related inflammation disease
Wave the effect of good, meanwhile, the adverse reaction that it occurs is equally extremely serious, serious gastrointestinal side effect such as be present.Cause
This, seeking new, efficient, less toxic anti-inflammatory drug becomes particularly important.
Flavanonol, English name：Flavanonol, such compound is flavonoids C-2, after the double bond hydrogenation of 3
Derivative, such plant component is most to carry hydroxyl or methoxyl group；When carrying hydroxyl on C-3 positions, flavanonol is commonly referred to as
Class.Flavanone kind composition is used as a kind of micro flavone compound, relatively limited in distributed in nature, to its correlative study
Report less, but the result of study of molecular biology shows that some compounds have significant anti-inflammatory activity in the recent period.
Biomedical research has an expectation all the time for medicine：Reduce lead optimization
Quantity and duration for the design cycle needed for high quality, safe and effective drug candidate；This is also domestic and international pharmaceutical chemistry
The target of family's diligent pursuit always.Effective molecule element design is an important method for realizing this target.This it
In, it is a kind of highly important thinking that the CH groups on aromatic rings are replaced by into N atoms.This modification can change many important
The physicochemical property of effector molecule, and improve the interaction between molecule-target spot, drug effect can be improved.From this view point,
" necessary nitrogen-atoms " (" necessary nitrogen atom "；Penningto, L.D.et al.2017) it has been proved to
It is a general design element.This mentality of designing can optimize the multinomial the physical-chemical parameters of drug candidate, while at double
Improve its crucial pharmacological parameters, so as to be embodied as medicine further application provide safeguard.With the active component in Chinese medicine
As lead compound, the stronger medicine of design synthesizing activity is always an important channel of new drug development.Therefore, screening contains
The new flavanone alcohols compound of N heteroaromatics is particularly significant for exploitation flavanonol kind new medicine.
Texifolin is exactly a kind of typical flavanone alcohols compound, is present in various plants composition.Pesudotsuga taxifolia
Element has multiple biological activities, wherein anti-inflammatory activity especially pronounced (Kim, Y.J.；Choi,S.E.；Lee,M.W.；Lee,
C.S.J.Pharm.Pharmacol.,2010,11,1465).The texifolin synthesized using this method, its anti-inflammatory activity
With the texifolin and indifference naturally extracted, using texifolin as lead compound, by the change to its B ring, it is particularly
The introducing of nitrogenous heteroaromatic, anti-inflammatory activity are greatly improved.
The content of the invention
Based on above the deficiencies in the prior art, technical problem solved by the invention is to design and synthesize a series of new
The flavanone alcohols compound of the heteroaromatic containing N, on the basis of activity research, it was found that these activity are splendid new to contain N
The flavanone alcohols compound of heteroaromatic, and the preparation method of this kind of compound is provided.
The present invention utilizes computer modeling technique, and based on acceptor combination principle, having designed and synthesized has structure shown in I
New flavanone alcohols compound.Cell experiment shows that these compounds discharge for the cells of RAW 264.7 that LPS is induced
Inflammatory factor has significant inhibitory action.
In order to solve the above-mentioned technical problem, the present invention provides a kind of flavanone alcohols compound of the heteroaromatic containing N, and it is special
Sign is there is following structure：
Wherein Ar substituents are in Formulas I OrIn one kind, and its refer to the position of substitution of compound should include N heteroaromatics on all energy
Substituted position.
The preparation method of the flavanone alcohols compound of a kind of heteroaromatic containing N, it is characterised in that comprise the following steps：
As the preferred of above-mentioned technical proposal, the flavanone alcohols compound of the heteroaromatic provided by the invention containing N and its
Preparation method further comprises the part or all of of following technical characteristic：
It is described Step 1: under stirring condition as the improvement of above-mentioned technical proposal, by Anhydrous potassium carbonate, 2,4,6- tri- hydroxyls
Benzoylformaldoxime is dissolved in acetone, return stirring 0.5~1h, slightly cold, is added dropwise chloromethyl ether under condition of ice bath, 5~8h of stirring reaction,
Potassium carbonate is filtered to remove, filtrate is spin-dried for, and obtains 2,4- dimethoxy methoxyl group -6- hydroxy acetophenones；The wherein described hydroxyls of 2,4,6- tri-
The ratio between amount of material of benzoylformaldoxime (II), Anhydrous potassium carbonate and chloromethyl ether is 1:2~5:1~3.
It is described Step 2: by 2,4- dimethoxy methoxyl group -6- hydroxy acetophenones, phase as the improvement of above-mentioned technical proposal
The nitrogenous fragrant formaldehyde and NaOH answered are dissolved in methanol, 10~15h of stirring reaction, are filtered, are obtained 2/,4/- dimethoxy methoxyl group-
6/- hydroxyl N heteroaromatic chalcone；Wherein described 2,4- dimethoxies methoxyl group -6- hydroxy acetophenones (III), contain N fragrance accordingly
The ratio between formaldehyde (IV) and NaOH amount of material is 1:1~2:8~10.
It is described Step 3: by 2 as the improvement of above-mentioned technical proposal/,4/- dimethoxy methoxyl group -6/- hydroxyl N heteroaromatics
Chalcone is dissolved in anhydrous tetrahydro furan, and the aqueous hydrogen peroxide solution and diethyl of mass percent 30% are added dropwise under condition of ice bath
Amine, 5~8h of stirring reaction, frozen water is added, filter, obtain 2,4- dimethoxy methoxyl group N heteroaromatic flavanonols；It is wherein described
2/,4/- dimethoxy methoxyl group -6/The aqueous hydrogen peroxide solution and second of-hydroxyl N heteroaromatics chalcone (V), mass percent 30%
The ratio between amount of material of diamines is 1:2~5:2~5.
It is described Step 4: under agitation as the improvement of above-mentioned technical proposal, by 5,7- dimethoxy methoxyl groups N virtues
Heterocycle flavanonol is dissolved in methanol, and concentrated hydrochloric acid is added dropwise, 1~3h of back flow reaction, adds frozen water, filters, obtains 5,7- dihydroxies
Base N heteroaromatic flavanonols；Wherein described 5,7- dimethoxies methoxyl group N heteroaromatics flavanonol (VI):The thing of concentrated hydrochloric acid
The ratio between amount of matter is 1:3~5.
As the improvement of above-mentioned technical proposal, described N aromatic heterocyclics are OrIn one kind, and it refers to the position of substitution of compound
All positions that can substitute in N heteroaromatics should be included.
A kind of application of the flavanone alcohols compound of the heteroaromatic containing N, it is characterised in that：The two of the heteroaromatic containing N
Hydrogen flavonoid drugs are used to prepare anti-inflammatory drug.
Compared with prior art, technical scheme has the advantages that：
The flavanone alcohols compound of the new heteroaromatic containing N of the present invention has stronger anti-inflammatory activity, wherein
There are some quite or more preferable than the activity of positive control Indomethacin and texifolin.Therefore it can be used for the medicine for preparing anti-inflammatory
Thing.
Described above is only the general introduction of technical solution of the present invention, in order to better understand the technological means of the present invention,
And can be practiced according to the content of specification, and in order to allow the above and other objects, features and advantages of the present invention can
Become apparent, below in conjunction with preferred embodiment, describe in detail as follows.
Embodiment
The following detailed description of the present invention embodiment, its as part of this specification, by embodiment come
Illustrate the principle of the present invention, other aspects of the present invention, feature and its advantage will become apparent by the detailed description.
Embodiment 1：2-(3/- pyridine radicals) -3,5,7- trihydroxy chroman-4-ons it is fully synthetic
(1) preparation of 2,4- dimethoxies methoxyl group -6- hydroxy acetophenones
The trihydroxy-acetophenones of 1g 2,4,6- are dissolved in 30ml acetone, add 2.88g Anhydrous potassium carbonates, return stirring
30min, it is slightly cold, 1.13ml chloromethyl ethers are added dropwise, continue to flow back, TLC plates are detected to reaction and completed, and add water quenching to go out reaction, acetic acid second
Ester is extracted, and anhydrous magnesium sulfate is dried, and is filtered, and revolving, obtains 2,4- dimethoxy methoxyl group -6- hydroxy acetophenone 1.32g, yield
86.62%.
(2) 3- pyridine radicals -2/,4/- dimethoxy methoxyl group -6/The preparation of-hydroxy chalcone
0.72g 3- pyridine carboxaldehydes are dissolved in 25mL absolute methanols, the sodium hydroxides of 5.20mL 50% are added under condition of ice bath
Solution, stirring, then add 1g 2,4- dimethoxy methoxyl group -6- hydroxy acetophenones.12h is reacted, reaction finishes is adjusted with concentrated hydrochloric acid
PH ≈ 6 are saved, there is yellow solid generation, is filtered, is recrystallized with absolute methanol, obtain 3- pyridine radicals -2/,4/- dimethoxy methoxyl group-
6/- hydroxy chalcone 1.33g, yield 88.01%.Yellow solid, fusing point：114~115 DEG C,1H NMR(DMSO-d6,400MHz)
δ 5.90 (s, 2H), 6.45-7.36 (m, 4H), 7.57 (d, 1H, J=15.6Hz), 8.00 (d, 1H, J=15.6Hz), 10.48
(s,1H),12.47(s,2H).
(3)2-(3/- pyridine radicals) -3- hydroxyl -5,7- dimethoxy methoxyl group chroman-4-ons preparation
By 1g 3- pyridine radicals -2/,4/- dimethoxy methoxyl group -6/- hydroxy chalcone is dissolved in 20ml anhydrous tetrahydro furans,
The aqueous hydrogen peroxide solution of 0.8ml mass percents 30% and 0.8g diethylamine are added dropwise under condition of ice bath, keeps under condition of ice bath
Reaction, TLC plates are detected to reaction and completed, and add 20ml cold water, are filtered, and washing, are recrystallized with absolute methanol, are obtained 2- (3/- pyrrole
Piperidinyl) -3- hydroxyl -5,7- dimethoxy methoxyl group chroman-4-ons 0.79g.
(4)2-(3/- pyridine radicals) -3,5,7- trihydroxy chroman-4-ons preparation
By 0.5g 2- (3/- pyridine radicals) -3- hydroxyl -5,7- dimethoxy methoxyl group chroman-4-ons are dissolved in 15ml methanol,
0.20ml concentrated hydrochloric acids are added dropwise, heating reflux reaction 1.5h, adds 10ml cold water, is extracted with ethyl acetate, merge organic layer, it is anhydrous
Magnesium sulfate is dried, and is boiled off solvent, the purifying of silica gel (100-200 mesh) column chromatography, is obtained 2- (3/- pyridine radicals) -3,5,7- trihydroxies
Chroman-4-on 0.25g, white solid.Fusing point：127.9~130.2 DEG C；1H NMR(400MHz,DMSO-d6)δ11.92(s,
1H), 10.82 (s, 1H), 8.80 (s, 1H), 8.55 (d, J=5.2Hz, 1H), 7.95 (d, J=8.0Hz, 1H), 7.43 (dd, J
=5.2,8.0Hz, 1H), 5.97 (s, 1H), 5.91 (s, 1H), 5.74 (s, 1H), 5.02 (d, J=12.4Hz, 1H), 4.52 (d,
J=12.4,1H)13C NMR(100MHz,DMSO-d6)δ197.48,167.28,164.27,163.25,148.72,146.79,
132.84,131.42,122.93,101.24,96.72,96.07,81.21,72.69.
Embodiment 2：2-(3/- pyridine radicals) -3,5,7- trihydroxy chroman-4-ons (a) anti-inflammatory activity research
(1) foundation of inflammatory model
Take the logarithm the culture cell in growth period, after Trypsin Induced, take the H-DMEM culture medium systems of 1% hyclone
Into 8 × 104Individual/ml single cell suspensions, uniformly it is inoculated in 96 orifice plates with every μ l of hole 100, puts 37 DEG C, 5%CO2Incubator culture,
Old culture medium is discarded after 12h.The complete medium containing LPS (1 μ g/mL) is added, continues to cultivate 24h, cellular inflammation model modeling
Complete.
(2) inflammatory factor IL-1 β, IL-6, TNF- ɑ in the RAW264.7 cell culture mediums of ELISA method detection LPS inductions
It is horizontal
Take the logarithm the culture cell in growth period, after Trypsin Induced, take the H-DMEM culture medium systems of 1% hyclone
Into 8 × 104Individual/ml single cell suspensions, uniformly it is inoculated in 96 orifice plates with every μ l of hole 100, puts 37 DEG C, 5%CO2Incubator culture,
Old culture medium is discarded after 12h.Modeling is carried out by the method under (1) inflammatory model item, after the completion of modeling, drug concentration is divided
Group, drug concentration are administered for the concentration needed.96 orifice plates are placed in 37 DEG C, 5%CO after administration2Cultivate in incubator, collected after 24h
Cell conditioned medium, by kit specification detection inflammatory factor IL-1 β, IL-6, TNF- ɑ amount after centrifugation.
As a result it is as shown in table 1：
Inflammatory factor IL-1 β of table 1, IL-6, TNF- ɑ testing result
Vs LPS group:*P<0.05,**P<0.01,***P<0.001(N=3) result shows：2-(3/- pyridine
Base) cells of the RAW 264.7 release inflammatory factor that induces for LPS of -3,5,7- trihydroxy chroman-4-ons (a) have it is significant
Inhibitory action, and its result and positive drug Indomethacin and texifolin activity are more preferable, can be used as anti-inflammatory drug.
Embodiment 3：2-(2/- furyl) -3,5,7- trihydroxy chroman-4-ons it is fully synthetic
(1) preparation of 2,4- dimethoxies methoxyl group -6- hydroxy acetophenones
The trihydroxy-acetophenones of 1g 2,4,6- are dissolved in 30ml acetone, add 2.88g Anhydrous potassium carbonates, return stirring
30min, it is slightly cold, 1.13ml chloromethyl ethers are added dropwise, continue to flow back, TLC plates are detected to reaction and completed, and add water quenching to go out reaction, acetic acid second
Ester is extracted, and anhydrous magnesium sulfate is dried, and is filtered, and revolving, obtains 2,4- dimethoxy methoxyl group -6- hydroxy acetophenone 1.32g, yield
86.62%.
(2) 2- furyls -2/,4/- dimethoxy methoxyl group -6/The preparation of-hydroxy chalcone
0.70g 2 furan carboxyaldehydes are dissolved in 25mL absolute methanols, the hydroxides of 5.20mL 50% are added under condition of ice bath
Sodium solution, stirring, then add 1g 2,4- dimethoxy methoxyl group -6- hydroxy acetophenones.12h is reacted, reaction, which finishes, uses concentrated hydrochloric acid
PH ≈ 6 are adjusted, there is yellow solid generation, is filtered, is recrystallized with absolute methanol, obtain 2- furyls -2/,4/- dimethoxy methoxy
Base -6/- hydroxy chalcone 1.38g, yield 87.01%.Yellow solid, fusing point：72~75 DEG C,1H NMR(DMSO-d6,
400MHz) δ 5.91 (s, 2H), 6.87-7.89 (m, 3H), 7.97 (d, 1H, J=15.2Hz), 8.25 (d, 1H, J=15.2Hz),
10.49(s,1H),12.50(s,2H).
(3)2-(2/- furyl) -3- hydroxyl -5,7- dimethoxy methoxyl group chroman-4-ons preparation
By 0.88g 2- furyls -2/,4/- dimethoxy methoxyl group -6/- hydroxy chalcone is dissolved in 20ml anhydrous tetrahydro furans
In, the aqueous hydrogen peroxide solution of 0.8ml mass percents 30% and 0.8g diethylamine are added dropwise under condition of ice bath, keeps condition of ice bath
Lower reaction, TLC plates are detected to reaction and completed, and add 20ml cold water, are filtered, and washing, are recrystallized with absolute methanol, are obtained 2- (2/-
Furyl) -3- hydroxyl -5,7- dimethoxy methoxyl group chroman-4-ons 0.88g.
(4)2-(2/- furyl) -3,5,7- trihydroxy chroman-4-ons preparation
By 0.45g 2- (2/- furyl) -3- hydroxyl -5,7- dimethoxy methoxyl group chroman-4-ons are dissolved in 15ml methanol,
0.20ml concentrated hydrochloric acids are added dropwise, heating reflux reaction 1.5h, adds 10ml cold water, is extracted with ethyl acetate, merge organic layer, it is anhydrous
Magnesium sulfate is dried, and is boiled off solvent, the purifying of silica gel (100-200 mesh) column chromatography, is obtained 2- (2/- furyl) -3,5,7- trihydroxies
Chroman-4-on 0.22g, white solid.Fusing point：137℃-138℃；1H NMR(400MHz,DMSO-d6)δ11.94(s,1H),
10.85 (s, 1H), 7.46 (s, 1H), 6.12~6.42 (m, 2H), 6.00 (s, 1H), 5.90 (s, 1H), 5.72 (d, J=
4.0Hz, 1H), 4.92 (d, J=12.0Hz, 1H), 4.52 (dd, J=12.0,4.0Hz, 1H)13C NMR(100MHz,DMSO-
d6)δ199.51,167.28,164.27,162.31,149.83,142.12,113.13,110.04,101.22,96.72,
95.68,81.17,72.41.
Embodiment 4：2-(2/- furyl) -3,5,7- trihydroxy chroman-4-ons (b) anti-inflammatory activity research
(1) foundation of inflammatory model
Take the logarithm the culture cell in growth period, after Trypsin Induced, take the H-DMEM culture medium systems of 1% hyclone
Into 8 × 104Individual/ml single cell suspensions, uniformly it is inoculated in 96 orifice plates with every μ l of hole 100, puts 37 DEG C, 5%CO2Incubator culture,
Old culture medium is discarded after 12h.The complete medium containing LPS (1 μ g/mL) is added, continues to cultivate 24h, cellular inflammation model modeling
Complete.
(2) inflammatory factor IL-1 β, IL-6, TNF- ɑ in the RAW264.7 cell culture mediums of ELISA method detection LPS inductions
It is horizontal
Take the logarithm the culture cell in growth period, after Trypsin Induced, take the H-DMEM culture medium systems of 1% hyclone
Into 8 × 104Individual/ml single cell suspensions, uniformly it is inoculated in 96 orifice plates with every μ l of hole 100, puts 37 DEG C, 5%CO2Incubator culture,
Old culture medium is discarded after 12h.Modeling is carried out by the method under (1) inflammatory model item, after the completion of modeling, drug concentration is divided
Group, drug concentration are administered for the concentration needed.96 orifice plates are placed in 37 DEG C, 5%CO after administration2Cultivate in incubator, collected after 24h
Cell conditioned medium, by kit specification detection inflammatory factor IL-1 β, IL-6, TNF- ɑ amount after centrifugation.
As a result it is as shown in table 1：
Inflammatory factor IL-1 β of table 2, IL-6, TNF- ɑ testing result
Vs LPS group:*P<0.05,**P<0.01,***P<0.001(N=3)
As a result show：Compound 2- (2/- furyl) RAW that is induced for LPS of -3,5,7- trihydroxy chroman-4-ons (b)
264.7 cells release inflammatory factor inhibitory action it is weaker, illustrate B rings align by its anti-inflammatory activity after furans heterocyclic substituted drastically under
Drop, without application value, it is impossible to used as anti-inflammatory drug.
The above embodiment of the present invention shows that the flavanone alcohols compound of the new heteroaromatic containing N of all synthesis is equal
With stronger anti-inflammatory activity, and found in toxicity research before, for such compound at 20 μM, it does not have cell toxicant
Property, therefore be further safe using them as medicinal application.And the flavanone alcohols compound of other heterocyclic substituteds resists
Scorching activity decrease or disappearance, it is impossible to used as anti-inflammatory drug.
Each raw material cited by the present invention, and bound, the section value of each raw material of the present invention, and technological parameter
Bound, the section value of (such as temperature, time) can realize the present invention, embodiment numerous to list herein.
Described above is the preferred embodiment of the present invention, can not limit the right model of the present invention with this certainly
Enclose, it is noted that for those skilled in the art, under the premise without departing from the principles of the invention, may be used also
To make some improvement and variation, these are improved and variation is also considered as protection scope of the present invention.
Claims (8)
1. the flavanone alcohols compound of a kind of heteroaromatic containing N, it is characterised in that there is following structure：
Wherein Ar substituents are in Formulas I In one kind, and its refer to the position of substitution of compound should include N heteroaromatics on all energy
Substituted position.
2. the preparation method of the flavanone alcohols compound of the heteroaromatic containing N as claimed in claim 1, it is characterised in that bag
Containing following steps：
Step 1: chloromethyl ether protects two phenolic hydroxyl groups
Step 2: the condensation reaction of carbonyl
Step 3: hydrogen peroxide annulation
Step 4: hydrochloric acid is deprotected
3. the preparation method of the flavanone alcohols compound of the heteroaromatic containing N as claimed in claim 2, it is characterised in that：Institute
State Step 1: under stirring condition, by Anhydrous potassium carbonate, 2, it is molten that 4,6- trihydroxy-acetophenones are dissolved in proper amount of acetone, return stirring 0.5
~1h, it is slightly cold, chloromethyl ether is added dropwise under condition of ice bath, 5~8h of stirring reaction, is filtered to remove potassium carbonate, filtrate is spin-dried for, and obtains 2,
4- dimethoxy methoxyl group -6- hydroxy acetophenones；Wherein described 2,4,6- trihydroxy-acetophenones (II), Anhydrous potassium carbonate and chloromethyl ether
The ratio between the amount of material be 1:2~5:1~3.
4. the preparation method of the flavanone alcohols compound of the heteroaromatic containing N as claimed in claim 2, it is characterised in that：Institute
State Step 2: 2,4- dimethoxy methoxyl group -6- hydroxy acetophenones, corresponding nitrogenous fragrant formaldehyde and NaOH are dissolved in methanol,
10~15h of stirring reaction, filter, obtain 2/,4/- dimethoxy methoxyl group -6/- hydroxyl the chalcone of heteroaromatic containing N；Wherein described 2,
The ratio between amount of material of 4- dimethoxy methoxyl group -6- hydroxy acetophenones (III), the corresponding formaldehyde of fragrance containing N (IV) and NaOH is 1:
1~2:8~10.
5. the preparation method of the flavanone alcohols compound of the heteroaromatic containing N as claimed in claim 2, it is characterised in that：Institute
State Step 3: by 2/,4/- dimethoxy methoxyl group -6/- hydroxyl the chalcone of heteroaromatic containing N is dissolved in anhydrous tetrahydro furan, in ice bath
Under the conditions of be added dropwise mass percent 30% aqueous hydrogen peroxide solution and diethylamine, 5~8h of stirring reaction, filter, obtain 2,4-
Dimethoxy methoxyl group N heteroaromatic flavanonols；Wherein described 2/,4/- dimethoxy methoxyl group -6/- hydroxyl N heteroaromatic chalcone
(V), the ratio between amount of material of the aqueous hydrogen peroxide solution of mass percent 30% and diethylamine is 1:2~5:2~5.
6. the preparation method of the flavanone alcohols compound of the heteroaromatic containing N as claimed in claim 2, it is characterised in that：Institute
State Step 4: under agitation, 5,7- dimethoxy methoxyl group N heteroaromatic flavanonols being dissolved in methanol, dense salt is added dropwise
Acid, 1~3h of back flow reaction, filter, obtain 5,7- dihydroxy N heteroaromatic flavanonols；Wherein described 5,7- dimethoxies methoxy
Base N heteroaromatics flavanonol (VI):The ratio between amount of material of concentrated hydrochloric acid is 1:3~5.
7. the preparation method of the flavanone alcohols compound of the heteroaromatic containing N as claimed in claim 2, it is characterised in that：Institute
The N aromatic heterocyclics stated are
In one kind, and its refer to the position of substitution of compound should include N heteroaromatics on it is all can substitution positions.
A kind of 8. application of the flavanone alcohols compound of heteroaromatic containing N, it is characterised in that：The dihydro of the heteroaromatic containing N
Flavonoid drugs are used to prepare anti-inflammatory drug.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1990482A (en) * | 2005-12-26 | 2007-07-04 | 浙江海正天华新药研发有限公司 | Flavanonol compounds and their production method and use |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1990482A (en) * | 2005-12-26 | 2007-07-04 | 浙江海正天华新药研发有限公司 | Flavanonol compounds and their production method and use |
Non-Patent Citations (3)
| Title |
|---|
| R.B. 西尔弗曼 编: "《有机药物化学》", 31 January 2008 * |
| 方雅静 等: "类黄酮构效关系研究进展", 《华中农业大学学报》 * |
| 赵雪巍 等: "黄酮类化合物的构效关系研究进展", 《中草药》 * |
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