CN103193749A - Preparation method of polyhydroxy flavonoids compound - Google Patents

Preparation method of polyhydroxy flavonoids compound Download PDF

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CN103193749A
CN103193749A CN2013101386160A CN201310138616A CN103193749A CN 103193749 A CN103193749 A CN 103193749A CN 2013101386160 A CN2013101386160 A CN 2013101386160A CN 201310138616 A CN201310138616 A CN 201310138616A CN 103193749 A CN103193749 A CN 103193749A
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methoxy
cinnamophenone
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ethyl acetate
sherwood oil
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阿吉艾克拜尔·艾萨
牛超
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Xinjiang Technical Institute of Physics and Chemistry of CAS
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Xinjiang Technical Institute of Physics and Chemistry of CAS
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Abstract

The invention relates to a preparation method of a polyhydroxy flavonoids compound. The preparation method comprises the steps of generating polysubstituted methoxyl-methoxy chalcone under the catalytic action of alkaline by using polysubstituted methoxyl-methoxy acetophenone and benzaldehyde as the raw materials and then removing a protecting group or carrying out ring closing reaction under the catalytic action of acid to prepare the polyhydroxy flavonoids compound. The reaction condition is temperate and the experimental procedures are simple.

Description

A kind of preparation method of poly-hydroxy flavonoid compound
Technical field
The present invention relates to a kind of preparation method of poly-hydroxy flavonoid compound.
Background technology
Flavonoid compound is extensive in distributed in nature, has multiple pharmacological effect, as anti-inflammatory, analgesia, antibiotic, antiviral, and Green Tea Extract oxidation, antitumor, hepatoprotective effect etc.
Feverfew stem of Anthelmintic Ironweed (Ver-nohia anthelminticaL.) is the exclusive Chinese medicinal materials in Xinjiang, only is grown in Keshen, the Aksu Prefecture in Xinjiang, and Uighur claims " card power cumin ", and the effect of dispersing cold for relieving pain, blood stasis dispersing and deswelling, desinsection removing beverage is arranged.The expelling parasite ringdove is clinical to be mainly used in treating vitiligo, and existing several be that the compound medicine of main component goes on the market with the stem of Anthelmintic Ironweed.As tie up medicine compound kaliziranding, insect-expelling saligna injection liquid, drive white etc.
This seminar of process discovers that to stem of Anthelmintic Ironweed effective constituent its flavone component promotes melanocyte propagation for activating tyrosine oxidase, and the treatment vitiligo has certain curative effect.
Studies show that, when having the hydroxyl of different quantities, position on the flavonoid compound molecule, can show the activation different to tyrosine oxidase.
The present invention is the condensation reaction by methyl phenyl ketone and phenyl aldehyde, introduces the hydroxyl of a plurality of different positionss and different numbers in the cinnamophenone molecule, thereby synthesizes a series of poly-hydroxy cinnamophenones and flavanone kind composition.
Summary of the invention
The object of the invention is; a kind of preparation method of poly-hydroxy flavonoid compound is provided; this compounds is raw material with polysubstituted methoxy methoxy benzoylformaldoxime and phenyl aldehyde; under the katalysis of alkali, generate polysubstituted methoxy methoxy base cinnamophenone earlier; again under the katalysis of acid, slough protecting group or ring closure reaction further takes place and prepare.This method reaction conditions gentleness, experimental procedure is simple and direct.
The preparation method of a kind of poly-hydroxy flavonoid compound of the present invention follows these steps to carry out:
A, the 10%NaOH aqueous solution is joined in the dehydrated alcohol, stir 10min under the ice bath;
B, polysubstituted methoxy methoxy benzoylformaldoxime is dissolved in the dehydrated alcohol, slowly drops in the step a system, stir 30min under the ice bath;
C, polysubstituted methoxy methoxy benzaldehyde is added in the step b reaction system again, after continuing ice bath stirring 30min, naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing, it is sherwood oil and ethyl acetate column chromatography gradient elution that residue is adopted eluent, obtains the polysubstituted methoxy methoxy base of intermediate cinnamophenone;
D, step c intermediate methoxy methoxy base cinnamophenone is dissolved in the dehydrated alcohol, slowly drip 3MHCl solution, in 78 ℃ of following back flow reaction of temperature, after the TLC detection reaction is complete, the vacuum desolventizing, it is sherwood oil and ethyl acetate column chromatography gradient elution that residue is adopted eluent, namely obtains poly-hydroxy cinnamophenone and flavanone.
The eluent volume ratio is sherwood oil: ethyl acetate=15:1-5 among the step c: 1.
The eluent volume ratio is sherwood oil: ethyl acetate=5:1-2 in the steps d: 1.
The preparation method of a kind of poly-hydroxy flavonoid compound of the present invention, by a kind of poly-hydroxy flavonoid compound that this method obtains, its structure is as leading to formula I, (II):
Figure BDA00003072035900021
R in the formula I wherein 1, R 2, R 3And R 4Be hydroxyl, R is H(R 1=R 2=R 3=R 4=OH, R=H); R 1And R 2Be hydroxyl, R 3, R 4With R be H(R 1=R 2=OH, R 3=R 4=R=H); R 1, R 2, R 4Be hydroxyl, R 3With R be H(R 1=R 2=R 4=OH, R 3=R=H); R 1, R 2, R 3, R 4With R all be hydroxyl (R 1=R 2=R 3=R 4=R=OH);
R in the formula II 2, R 3, R 4Be hydroxyl, R is H(R2=R3=R4=OH, R'=H); R 2Be hydroxyl, R 3, R 4With R be H(R 2=OH, R 3=R 4=R=H); R 2And R 4Be hydroxyl, R 3With R be H(R 2=R 3=OH, R 3=R=H); R 2, R 3, R 4With R all be OH(R 2=R 3=R 4=R=OH).
The preparation method of a kind of poly-hydroxy flavonoid compound of the present invention, it is the Claisen – Schmidt reaction by methyl phenyl ketone and phenyl aldehyde, introduce the hydroxyl of a plurality of different positionss and different numbers in the cinnamophenone molecule, thereby synthetic a series of poly-hydroxy cinnamophenones and flavanone kind composition, chemical equation is:
Figure BDA00003072035900031
R wherein 1', R 2', R 3' and R 4' be the methoxy methoxy base, R ' is H(R 1'=R 2'=R 3'=R 4'=OCH 2OCH 3, R '=H); R 1' and R 2' be the methoxy methoxy base, R 3', R 4' and R ' be H(R 1'=R 2'=OCH 2OCH 3, R 3'=R 4'=R=H); R 1', R 2', R 4' be the methoxy methoxy base, R 3' and R ' be H(R 1'=R 2'=R 4'=OCH 2OCH 3, R 3'=R '=H); R 1', R 2', R 3', R 4' all be the methoxy methoxy base, R ' is hydroxyl (R 1'=R 2'=R 3'=R 4'=OCH 2OCH 3, R '=OH).
R in the formula I 1, R 2, R 3And R 4Be hydroxyl, R is H(R 1=R 2=R 3=R 4=OH, R=H); R 1And R 2Be hydroxyl, R 3, R 4With R be H(R 1=R 2=OH, R 3=R 4=R=H); R 1, R 2, R 4Be hydroxyl, R 3With R be H(R 1=R 2=R 4=OH, R 3=R=H); R 1, R 2, R 3, R 4With R all be hydroxyl (R 1=R 2=R 3=R 4=R=OH).
R in the formula II 2, R 3, R 4Be hydroxyl, R is H(R2=R3=R4=OH, R=H); R 2Be hydroxyl, R 3, R 4With R be H(R 2=OH, R 3=R 4=R=H); R 2And R 4Be hydroxyl, R 3With R be H(R 2=R 3=OH, R 3=R=H); R 2, R 3, R 4With R all be OH(R 2=R 3=R 4=R=OH).
Embodiment
The present invention is further described according to embodiment, but the present invention is not limited only to these embodiment;
Reagent: all reagent are commercially available analytical pure;
Embodiment 1:3,4,2 ', 4 '-tetrahydroxy cinnamophenone (purple fourth of the twelve Earthly Branches cinnamophenone) and 7,3 ', 4 '-preparation of trihydroxy-flavanone (purple fourth of the twelve Earthly Branches element):
A, 10%NaOH aqueous solution 0.34g is joined in the dehydrated alcohol, stir 10min under the ice bath;
B, with 0.24g (1.0mmol) 2,4-dimethoxy methoxyacetophenone is dissolved in the dehydrated alcohol, slowly drops in the step a system, stirs 30min under the ice bath;
C, again with 0.226g(1.0mmol) 3,4-dimethoxy methoxybenzaldehyde adds in the step b reaction system, after continuing ice bath stirring 30min, rise to room temperature naturally and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=15: 1 column chromatography gradient elutions namely gets intermediate 3,4,2 ', 4 '-tetramethyl oxygen methoxyl group cinnamophenone;
D, with step c gained intermediate 3,4,2 ', 4 '-tetramethyl oxygen methoxyl group cinnamophenone 0.448g(1.0mmol) be dissolved in the dehydrated alcohol, slowly drip 3MHCl solution, in 78 ℃ of following back flow reaction of temperature, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=3: 1 column chromatography gradient elutions, namely get 3,4,2 ', 4 '-the purple fourth of the twelve Earthly Branches of tetrahydroxy cinnamophenone 0.14g(cinnamophenone) and 7,3 ', 4 '-the purple fourth of the twelve Earthly Branches of trihydroxy-flavanone 0.08g(element);
3,4,2 ', 4 '-tetrahydroxy cinnamophenone nuclear magnetic data:
1HNMR(400MHz,CD 3OD)δ7.95(d,J=8.9Hz,1H),7.73(d,J=15.3Hz,1H),7.59–7.49(d,J=15.2,1H),7.18(s,1H),7.12(d,J=8.2Hz,1H),6.82(d,J=8.2Hz,1H),6.42(dd,J=8.9,2.1Hz,1H),6.29(d,J=2.1Hz,1H)；
7,3 ', 4 '-trihydroxy-flavanone nuclear magnetic data:
1HNMR(400MHz,CD 3OD)δ7.73(d,J=8.7Hz,1H),6.93(d,J=1.3Hz,1H),6.80(d,J=3.0Hz,1H),6.50(dd,J=8.7,2.2Hz,1H),6.36(d,J=2.2Hz,1H),5.32(dd,J=12.8,2.9Hz,1H),3.01(dd,J=16.9,12.9Hz,1H),2.70(dd,J=16.9,3.0Hz,1H)。
Embodiment 2:2 ', 4 '-preparation of dihydroxyl cinnamophenone and 7-hydroxyl dihydro anthoxanthin:
A, 10%NaOH aqueous solution 0.34g is joined in the dehydrated alcohol, stir 10min under the ice bath;
B, with 0.24g (1.0mmol) 2,4-dimethoxy methoxyacetophenone is dissolved in the dehydrated alcohol, slowly drops in the step a system, stirs 30min under the ice bath;
C, again with 0.106g(1.0mmol) phenyl aldehyde adds in the step b reaction system, after continuing ice bath stirring 30min, naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=10: 1 column chromatography gradient elutions, namely get intermediate 2 ', 4 '-dimethoxy methoxyl group cinnamophenone;
D, with step c gained intermediate 2 ', 4 '-dimethoxy methoxyl group cinnamophenone 0.382g(1.0mmol) be dissolved in the dehydrated alcohol, slowly drip 3MHCl solution, in 78 ℃ of following back flow reaction of temperature, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=5: 1 column chromatography gradient elutions, namely get 2 ', 4 '-dihydroxyl cinnamophenone 0.14g and 7-hydroxyl dihydro anthoxanthin 0.07g;
2 ', 4 '-dihydroxyl cinnamophenone nuclear-magnetism:
1HNMR(400MHz,CD 3OD)δ8.02(d,J=8.9Hz,1H),7.90–7.71(m,4H),7.53–7.35(m,3H),6.45(dd,J=8.9,2.4Hz,1H),6.33(d,J=2.4Hz,1H)；
7-hydroxyl dihydro anthoxanthin nuclear-magnetism:
1HNMR(400MHz,CD 3OD)δ7.64(d,J=8.7Hz,1H),7.41(d,J=7.5Hz,2H),7.29(m，3H),6.42(dd,J=8.7,1.4Hz,1H),6.30(d,J=1.8Hz,1H),5.40(dd,J=12.8,2.6Hz,1H),2.94(dd,J=16.9,12.9Hz,1H),2.67(dd,J=16.9,2.8Hz,1H)。
Embodiment 3:4,2 ', 4 '-trihydroxy-cinnamophenone (isoliquiritigenin) and 7,4 '-preparation of dihydroxyl flavanone (Liquiritigenin):
A, 10%NaOH aqueous solution 0.34g is joined in the dehydrated alcohol, stir 10min under the ice bath;
B, with 0.24g (1.0mmol) 2,4-dimethoxy methoxyacetophenone is dissolved in the dehydrated alcohol, slowly drops in the step a system, stirs 30min under the ice bath;
C, again with 0.166g(1.0mmol) 4-methoxy methoxy benzaldehyde adds in the step b reaction system, after continuing ice bath stirring 30min, naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=10: 1 column chromatography gradient elutions namely gets intermediate 4,2 ', 4 '-dimethoxy methoxyl group cinnamophenone;
D, with step c gained intermediate 4,2 ', 4 '-dimethoxy methoxyl group cinnamophenone 0.388g(1.0mmol) be dissolved in the dehydrated alcohol, slowly drip 3MHCl solution, in 78 ℃ of following back flow reaction of temperature, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=3: 1 column chromatography gradient elutions, namely get 4,2 ', 4 '-trihydroxy-cinnamophenone (isoliquiritigenin) 0.13g and 7,4 '-dihydroxyl flavanone 0.09g(Liquiritigenin);
4,2 ', 4 '-trihydroxy-cinnamophenone nuclear-magnetism:
1HNMR(400MHz,CD3OD)δ7.97(d,J=8.9Hz,1H),7.79(d,J=15.4Hz,1H),7.69–7.54(m,3H),6.85(d,J=8.7Hz,2H),6.41(dd,J=8.9,2.3Hz,1H),6.29(d,J=2.3Hz,1H)；
7,4 '-dihydroxyl flavanone nuclear-magnetism:
1HNMR(400MHz,CD3OD)δ7.73(d,J=8.7Hz,1H),7.33(d,J=8.6Hz,2H),6.82(d,J=8.6Hz,2H),6.50(dd,J=8.7,2.2Hz,1H),6.36(d,J=2.2Hz,1H),5.39(dd,J=13.1,2.8Hz,1H),3.06(dd,J=16.9,13.1Hz,1H),2.70(dd,J=16.9,2.9Hz,1H)。
Embodiment 4:3,4,2 ', 4 ', 6 '-penta hydroxy group cinnamophenone and 5,7,3 ', 4 '-preparation of tetrahydroxy flavanone:
A, 10%NaOH aqueous solution 0.34g is joined in the dehydrated alcohol, stir 10min under the ice bath;
B, with 0.256g (1.0mmol) 2-hydroxyl-4,6-dimethoxy methoxyacetophenone is dissolved in the dehydrated alcohol, slowly drops in the step a system, stirs 30min under the ice bath;
C, again with 0.226g(1.0mmol) 3,4-dimethoxy methoxybenzaldehyde adds in the step b reaction system, after continuing ice bath stirring 30min, rise to room temperature naturally and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=15: 1 column chromatography gradient elutions namely gets intermediate 2-hydroxyl-3,4,4 ', 6 '-tetramethyl oxygen methoxyl group cinnamophenone;
D, with step c gained intermediate 2-hydroxyl-3,4,4 ', 6 '-tetramethyl oxygen methoxyl group cinnamophenone 0.464g(1.0mmol) be dissolved in the dehydrated alcohol, slowly drip 3MHCl solution, in 78 ℃ of following back flow reaction of temperature, after the TLC detection reaction is complete, the vacuum desolventizing, it is the volume ratio sherwood oil that residue is adopted eluent: ethyl acetate=2: 1 column chromatography gradient elutions, namely get 3,4,2 ', 4 ', 6 '-penta hydroxy group cinnamophenone 0.16g and 5,7,3 ', 4 '-tetrahydroxy flavanone 0.10g;
3,4,2 ', 4 ', 6 '-penta hydroxy group cinnamophenone nuclear-magnetism:
1HNMR(400MHz,CD3OD)δ8.03(d,J=15.5Hz,1H),7.64(d,J=15.5Hz,1H),7.11(d,J=1.9Hz,1H),6.98(dd,J=8.2,1.9Hz,1H),6.79(d,J=8.1Hz,1H),5.85(s,2H)；
5,7,3 ', 4 '-tetrahydroxy flavanone nuclear-magnetism:
1HNMR(400MHz,CD3OD)δ6.92(s,1H),6.83–6.74(m,2H),5.89(dd,J=8.2,2.1Hz,2H),5.29(dd,J=12.7,3.0Hz,1H),3.07(dd,J=17.1,12.7Hz,1H),2.70(dd,J=17.1,3.0Hz,1H)。

Claims (3)

1. the preparation method of a poly-hydroxy flavonoid compound is characterized in that following these steps to carrying out:
A, the 10% NaOH aqueous solution is joined in the dehydrated alcohol, stir 10min under the ice bath;
B, polysubstituted methoxy methoxy benzoylformaldoxime is dissolved in the dehydrated alcohol, slowly drops in the step a system, stir 30min under the ice bath;
C, polysubstituted methoxy methoxy benzaldehyde is added in the step b reaction system again, after the continuation ice bath stirs 30 min, naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing, it is sherwood oil and ethyl acetate column chromatography gradient elution that residue is adopted eluent, obtains the polysubstituted methoxy methoxy base of intermediate cinnamophenone;
D, step c intermediate methoxy methoxy base cinnamophenone is dissolved in the dehydrated alcohol, slowly drip 3M HCl solution, in 78 ℃ of following back flow reaction of temperature, after the TLC detection reaction is complete, the vacuum desolventizing, it is sherwood oil and ethyl acetate column chromatography gradient elution that residue is adopted eluent, namely obtains poly-hydroxy cinnamophenone and flavanone.
2. according to the described method of claim 1, it is characterized in that the eluent volume ratio is sherwood oil: ethyl acetate=15:1-5 1 among the step c.
3. according to the described method of claim 1, it is characterized in that the eluent volume ratio is sherwood oil: ethyl acetate=5:1-2 1 in the steps d.
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Cited By (5)

* Cited by examiner, † Cited by third party
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CN103524475A (en) * 2013-10-21 2014-01-22 宁夏宝塔石化科技实业发展有限公司 Method for synthesizing polyhydroxy flavanone thiosemicarbazone Schiff base
CN104388489A (en) * 2014-11-10 2015-03-04 中山大学 Microbial hydroxylation conversion method and application of flavone compounds
CN105348245A (en) * 2015-12-01 2016-02-24 陕西嘉禾生物科技股份有限公司 Eriodictyol synthesis method
CN105481706A (en) * 2014-09-19 2016-04-13 四川大学 2-hydroxyl chalcone compound as well as preparation method and purpose thereof
CN109400567A (en) * 2018-12-05 2019-03-01 华中药业股份有限公司 A method of synthesis glycyrrhizin

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103524475A (en) * 2013-10-21 2014-01-22 宁夏宝塔石化科技实业发展有限公司 Method for synthesizing polyhydroxy flavanone thiosemicarbazone Schiff base
CN105481706A (en) * 2014-09-19 2016-04-13 四川大学 2-hydroxyl chalcone compound as well as preparation method and purpose thereof
CN105481706B (en) * 2014-09-19 2017-08-25 四川大学 The Hydroxylated Chalcones and Related compound of one class 2, preparation method and use
CN104388489A (en) * 2014-11-10 2015-03-04 中山大学 Microbial hydroxylation conversion method and application of flavone compounds
CN104388489B (en) * 2014-11-10 2017-10-27 中山大学 A kind of microbial hydroxylation method for transformation of chromocor compound and application
CN105348245A (en) * 2015-12-01 2016-02-24 陕西嘉禾生物科技股份有限公司 Eriodictyol synthesis method
CN109400567A (en) * 2018-12-05 2019-03-01 华中药业股份有限公司 A method of synthesis glycyrrhizin

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Application publication date: 20130710