CN104803962A - Preparation method of flavonoid-glycine schiff base - Google Patents
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Abstract
The invention relates to a preparation method of a flavonoid-glycine schiff base. The method is as below: respectively dissolving quercetin, luteolin, apigenin, myricetin amd dihydroquercetin in absolute ethyl alcohol, respectively adding to a certain amount of N2OH alcohol solution, carrying out radiation in a microwave device while magnetic stirring, and then respectively adding to a certain amount of glycine an alcohol solution for reaction to produce precipitate insoluble in ethanol, tracking the detection reaction by TLC, and conducting alcohol wash to obtain the product. The compound synthesized by the preparation method preserves the mother nucleus structure of flavonoid compound and anti-tumor activity; the flavonoid-glycine schiff base synthesized with glycine has water solubility, targeting and anti-tumor activity better than the flavonoid compound; and the preparation method is simple, high in yield and low in cost.
Description
Technical field: the preparation method that the present invention relates to a kind of flavones-glycine Schiff base, the flavonoid medicine related to is specially the Schiff bases compound that Quercetin, luteolin, apigenin, ampelopsin and dihydroquercetin and glycine condensation are formed.
Background technology: flavonoid compound is extensively present in natural one large class natural organic-compound, has C
6-C
3-C
6basic configuration, for the metabolite of plant materials Polyphenols, flavonoid compound has anticancer, antitumor, resisting cardiovascular disease, relieving inflammation and relaxing pain, immunomodulatory, hypoglycemic, treatment osteoporosis, antibacterial, antiviral, anti-oxidant, anti-ageing, the effects such as radioprotective, therefore, flavonoid compound is the class natural product that current people compare concern, become the focus that domestic and international natural drug develops research, flavonoid compound effect is extensive, but because flavonoid compound is water-soluble poor, this compounds absorbs and does not absorb very less or completely in enteron aisle, limit their clinical application.For this problem, domestic and international investigator actively innovates and carries out structural modification to it, mainly concentrate on 2,3, C ring, 5,6,7,8, A ring, B ring 2 ', 3 ', 4 ' position, substituting group mainly contains halogen, alkane (oxygen) base, aryl, pyridyl, amino, carboxyl, sulfonic group, phosphate etc., by enrich its kind and change its chemical property improve flavonoid compound water-soluble, strengthen its anti-tumor activity, improve its bioavailability.Although the structural modification of flavonoid compound achieves achievement, but because the modification group kind introduced is different, configurations, analogy is poor, be difficult to the screening modification group introduced being carried out to " having object ", be therefore just difficult to the flavonoid anti-cancer agent of rational design synthesizing efficient on the basis of analytic induction " structure activity relationship ".
Summary of the invention: the object of the invention is to overcome above-mentioned shortcoming, a kind of preparation method of flavones-glycine Schiff base is provided, select minimum amino acids glycine, modified is strong and play a key effect in cancer cell multiplication, derivatize is carried out to flavonoid compound, and good water solubility, stability is high, the flavones that targeting is strong-glycine Schiff base compound.The object of the present invention is achieved like this, and in the ethanol that flavones is housed, add glycine in the basic conditions, microwave-assisted makes the amino of glycine and the carbonyl condensation of flavones form Schiff's base.
By 0.302g Quercetin, 0.2286g luteolin, 0.4035g apigenin, 0.318 ampelopsin, 0.304 dihydroquercetin is dissolved in 50 mL dehydrated alcohols respectively, add 0.08 g respectively, 0.04g, 0.08g, 0.08g, NaOH alcoholic solution 1 mL of 0.08g, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, add glycine 0.046g respectively again, 0.075g, 0.075g, 0.075g, the alcoholic solution 10mL of 0.075g, react 0.5 h, generate the precipitation being insoluble to ethanol, react with TLC tracing detection, when after the completely dissolve of raw material point, proved response is complete, alcohol wash 2 times, obtain product.The glycine added also can be L-Ala, Methionin, aspartic acid.Mother nucleus structure and the anti-tumor activity of chromocor compound is remained with the compound that this preparation method synthesizes, synthesized flavones-glycine Schiff base with glycine, it is water-soluble, targeting and anti-tumor activity be all better than former flavonoid compound, preparation method is simple, productive rate is high, and cost is low.
Specific embodiment:
Embodiment 1: the synthesis of Quercetin-glycine Schiff base
Get Quercetin 1mmol(0.302 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 0.5 mmol(0.046g) alcoholic solution 10mL, react 0.5 h, generate the precipitation being insoluble to ethanol, react with TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown Compound I
13c-NMR(D
2o)
δ: 127.33(C-2), 112.01(C-3), 164.91(C-4), 159.88(C-5), 97.78(C-6), 162.66 (C-7), 97.78(C-8), 162.66(C-9), 97.78(C-10), 128.33(C-1 '), 120.39(C-2 '), 145.99(C-3 '), 143.77(C-4 '), 116.80(C-5 '), 114.42(C-6 '), 173.48 57.52(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound I
embodiment 2the synthesis of luteolin-glycine Schiff base
Get 1mmol(0.2286 g) luteolin is dissolved in 50 mL dehydrated alcohols, add 1 mmol(0.04 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generates the precipitation being insoluble to ethanol, reacts with TLC tracing detection, after the raw material point completely dissolve of luteolin, proved response is complete, alcohol wash 2 times, filters and obtains brown compound ii
13c-NMR(D
2o)
δ: 161.93(C-2), 85.97(C-3), 164.09(C-4), 159.62(C-5), 98.55(C-6), 161.93 (C-7), 98.55(C-8), 161.93(C-9), 102.65(C-10), 128.83(C-1 '), 119.99(C-2 '), 144.99(C-3 '), 142.43(C-4 '), 116.52(C-5 '), 112.74(C-6 '), 171.00 56.25(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound ii
embodiment 3the synthesis of apigenin-glycine Schiff base
Get apigenin 1.5mmol(0.4035 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generates the precipitation being insoluble to ethanol, reacts with TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown compound III
13c-NMR(D
2o)
δ: 162.82(C-2), 87.50(C-3), 164.40(C-4), 159.62(C-5), 99.90(C-6), 162.80 (C-7), 98.03(C-8), 159.62(C-9), 108.04(C-10), 128.66(C-1 '), 128.66(C-2 '), 116.77(C-3 '), 154.23(C-4 '), 119.18(C-5 '), 128.66(C-6 '), 177.55 56.71(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound III
embodiment 4the synthesis of ampelopsin-glycine Schiff base
Get ampelopsin 1mmol(0.318 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, in microwave instrument, carry out radiation, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generates the precipitation being insoluble to ethanol, reacts with TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown compounds Ⅳ
13c-NMR(D
2o)
δ: 135.24(C-2), 112.15(C-3), 164.76(C-4), 160.14(C-5), 98.03(C-6), 161.68 (C-7), 95.21(C-8), 160.14(C-9), 107.01(C-10), 128.83(C-1 '), 108.30(C-2 '), 147.30(C-3 '), 130.88(C-4 '), 144.22(C-5 '), 109.58(C-6 '), 172.97 55.94(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compounds Ⅳ
embodiment 5the synthesis of dihydroquercetin-glycine Schiff base
Get dihydroquercetin 1mmol(0.304 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generate the precipitation being insoluble to ethanol, with the reaction of TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown compound V.
13c-NMR(D
2o)
δ: 82.38(C-2), 71.21(C-3), 164.24(C-4), 159.88(C-5), 94.70(C-6), 161.16 (C-7), 99.06(C-8), 162.96(C-9), 103.68(C-10), 134.47(C-1 '), 126.77(C-2 '), 145.76(C-3 '), 144.48(C-4 '), 119.72(C-5 '), 115.67(C-6 '), 171.04 56.46(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound V
The glycine more than added also can be L-Ala, Methionin, aspartic acid.
flavonoid compound compares with flavones-glycine Schiff base solubleness
| Compound title | Solubleness (g/100mL) |
| Quercetin | — |
| Luteolin | — |
| Apigenin | — |
| Ampelopsin | — |
| Dihydroquercetin | — |
| Compound title | Solubleness (g/100mL) |
| Quercetin-glycine Schiff base | 5.4 |
| Luteolin-glycine Schiff base | 1.83 |
| Apigenin-glycine Schiff base | 3.26 |
| Ampelopsin-glycine Schiff base | 2.33 |
| Dihydroquercetin-glycine Schiff base | 3.17 |
flavones-glycine Schiff base is to growth of tumour cell Inhibition test
Get the MCF-7 cell routine digestion being in logarithmic phase, make 5 × 10 with 1640 perfect mediums containing 10% foetal calf serum
4individual mL
-1cell suspension.100 μ L cell suspensions are inoculated in every hole, 37 DEG C, saturated humidity, 5%CO
2overnight incubation under condition.After cell attachment, respectively by 5 kinds of flavones ammonia-glycine Schiff base solution according to following concentration 10,20,40,80,160,320 mgmL
-1, every hole 100 μ L adds 96 orifice plates successively, and each concentration establishes 5 multiple holes, repeats 3 times, continues to hatch 24h.After arriving predetermined incubation time, in 96 orifice plates, every hole adds the MTT(5 mgmL of 20 μ L
-1) solution, after lucifuge continues cultivation 4 h, carefully inhale the supernatant liquor abandoned in culture hole, every hole adds DMSO 150 μ L, vibrates gently, purple crystal is dissolved completely, and the inherent 492nm wavelength place microplate reader of 10 min surveys its absorption value (OD).And be calculated as follows inhibiting rate: inhibitory rate of cell growth=(1-experimental group OD value/control group OD value) × 100%.Result is as follows:
table one Quercetin-glycine Schiff base is to the restraining effect result of breast cancer cell MCF-7
| Group | Drug level (mgmL -1) | Inhibiting rate (%) |
| Blank | 0 | 0% |
| Quercetin-glycine | 10 | 35% |
| Quercetin-glycine | 20 | 47% |
| Quercetin-glycine | 40 | 50% |
| Quercetin-glycine | 80 | 58% |
| Quercetin-glycine | 160 | 62% |
| Quercetin-glycine | 320 | 73% |
table two luteolin-glycine Schiff base is to the restraining effect result of breast cancer cell MCF-7
| Group | Drug level (mgmL -1) | Inhibiting rate (%) |
| Blank | 0 | 0% |
| Luteolin-glycine | 10 | 10% |
| Luteolin-glycine | 20 | 19% |
| Luteolin-glycine | 40 | 32% |
| Luteolin-glycine | 80 | 34% |
| Luteolin-glycine | 160 | 37% |
| Luteolin-glycine | 320 | 57% |
table three apigenin-glycine Schiff base is to the restraining effect result of breast cancer cell MCF-7
| Group | Drug level (mgmL -1) | Inhibiting rate (%) |
| Blank | 0 | 0% |
| Apigenin-glycine | 10 | 28% |
| Apigenin-glycine | 20 | 43% |
| Apigenin-glycine | 40 | 47% |
| Apigenin-glycine | 80 | 54% |
| Apigenin-glycine | 160 | 63% |
| Apigenin-glycine | 320 | 71% |
table four ampelopsin-glycine Schiff base is to the restraining effect result of breast cancer cell MCF-7
| Group | Drug level (mgmL -1) | Inhibiting rate (%) |
| Blank | 0 | 0% |
| Ampelopsin-glycine | 10 | 21% |
| Ampelopsin-glycine | 20 | 24% |
| Ampelopsin-glycine | 40 | 25% |
| Ampelopsin-glycine | 80 | 26% |
| Ampelopsin-glycine | 160 | 29.5% |
| Ampelopsin-glycine | 320 | 32% |
table five dihydroquercetin-glycine Schiff base is to the restraining effect result of breast cancer cell MCF-7
| Group | Drug level (mgmL -1) | Inhibiting rate (%) |
| Blank | 0 | 0% |
| Dihydroquercetin-glycine | 10 | 20% |
| Dihydroquercetin-glycine | 20 | 24% |
| Dihydroquercetin-glycine | 40 | 29% |
| Dihydroquercetin-glycine | 80 | 34% |
| Dihydroquercetin-glycine | 160 | 49% |
| Dihydroquercetin-glycine | 320 | 62% |
Claims (3)
1.
a preparation method for flavones-glycine Schiff base, is characterized in that: in the ethanol that flavones is housed, add glycine in the basic conditions, microwave-assisted makes the amino of glycine and the carbonyl condensation of flavones form Schiff's base,
A, get Quercetin 1mmol(0.302 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 0.5 mmol(0.046g) alcoholic solution 10mL, react 0.5 h, generate the precipitation being insoluble to ethanol, react with TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown Compound I
13c-NMR(D
2o)
δ: 127.33(C-2), 112.01(C-3), 164.91(C-4), 159.88(C-5), 97.78(C-6), 162.66 (C-7), 97.78(C-8), 162.66(C-9), 97.78(C-10), 128.33(C-1 '), 120.39(C-2 '), 145.99(C-3 '), 143.77(C-4 '), 116.80(C-5 '), 114.42(C-6 '), 173.48 57.52(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound I
B, get 1mmol(0.2286 g) luteolin is dissolved in 50 mL dehydrated alcohols, add 1 mmol(0.04 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generates the precipitation being insoluble to ethanol, reacts with TLC tracing detection, after the raw material point completely dissolve of luteolin, proved response is complete, alcohol wash 2 times, filters and obtains brown compound ii
13c-NMR(D
2o)
δ: 161.93(C-2), 85.97(C-3), 164.09(C-4), 159.62(C-5), 98.55(C-6), 161.93 (C-7), 98.55(C-8), 161.93(C-9), 102.65(C-10), 128.83(C-1 '), 119.99(C-2 '), 144.99(C-3 '), 142.43(C-4 '), 116.52(C-5 '), 112.74(C-6 '), 171.00 56.25(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound ii
C, get apigenin 1.5mmol(0.4035 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generates the precipitation being insoluble to ethanol, reacts with TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown compound III
13c-NMR(D
2o)
δ: 162.82(C-2), 87.50(C-3), 164.40(C-4), 159.62(C-5), 99.90(C-6), 162.80 (C-7), 98.03(C-8), 159.62(C-9), 108.04(C-10), 128.66(C-1 '), 128.66(C-2 '), 116.77(C-3 '), 154.23(C-4 '), 119.18(C-5 '), 128.66(C-6 '), 177.55 56.71(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound III
D, get ampelopsin 1mmol(0.318 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generates the precipitation being insoluble to ethanol, reacts with TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown compounds Ⅳ
13c-NMR(D
2o)
δ: 135.24(C-2), 112.15(C-3), 164.76(C-4), 160.14(C-5), 98.03(C-6), 161.68 (C-7), 95.21(C-8), 160.14(C-9), 107.01(C-10), 128.83(C-1 '), 108.30(C-2 '), 147.30(C-3 '), 130.88(C-4 '), 144.22(C-5 '), 109.58(C-6 '), 172.97 55.94(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compounds Ⅳ
E, get dihydroquercetin 1mmol(0.304 g) be dissolved in 50 mL dehydrated alcohols, add 2 mmol(0.08 g) NaOH alcoholic solution 1 mL, radiation is carried out in microwave instrument, magnetic agitation simultaneously, temperature is set to 56 DEG C, power 400W, then add glycine 1 mmol(0.075g) alcoholic solution 10mL, reaction 0.5h, generate the precipitation being insoluble to ethanol, with the reaction of TLC tracing detection, after the raw material point completely dissolve of Quercetin, proved response is complete, alcohol wash 2 times, filters and obtains brown compound V.
2.
2. 13c-NMR(D
2o)
δ: 82.38(C-2), 71.21(C-3), 164.24(C-4), 159.88(C-5), 94.70(C-6), 161.16 (C-7), 99.06(C-8), 162.96(C-9), 103.68(C-10), 134.47(C-1 '), 126.77(C-2 '), 145.76(C-3 '), 144.48(C-4 '), 119.72(C-5 '), 115.67(C-6 '), 171.04 56.46(is respectively C=O, CH in glycine
2), composite structure is as follows:
Compound V
The preparation method of flavones-glycine Schiff base according to claim 1, is characterized in that: the glycine added also can be L-Ala, Methionin, aspartic acid.
3. the preparation method of flavones-glycine Schiff base according to claim 1, is characterized in that: flavonoid compound comprises Quercetin, luteolin, apigenin, ampelopsin, dihydroquercetin.
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| CN111995607A (en) * | 2020-08-31 | 2020-11-27 | 厦门一三九生物科技有限公司 | Preparation method of antiviral phenyl selenide |
| CN113304113A (en) * | 2021-05-31 | 2021-08-27 | 桂林医学院 | Co-amorphous solid dispersion for improving dissolution of quercetin and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417657A (en) * | 2017-07-31 | 2017-12-01 | 广东药科大学 | A kind of myricetin Schiff bases changes structure thing and its preparation method and application |
| CN107417657B (en) * | 2017-07-31 | 2020-07-17 | 广东药科大学 | Myricetin Schiff base modified substance and preparation method and application thereof |
| CN111995607A (en) * | 2020-08-31 | 2020-11-27 | 厦门一三九生物科技有限公司 | Preparation method of antiviral phenyl selenide |
| CN111995607B (en) * | 2020-08-31 | 2023-04-21 | 厦门一三九生物科技有限公司 | Preparation method of antiviral phenyl selenide |
| CN113304113A (en) * | 2021-05-31 | 2021-08-27 | 桂林医学院 | Co-amorphous solid dispersion for improving dissolution of quercetin and preparation method thereof |
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