CN110283182A - A kind of preparation method of isoflavone compound - Google Patents

A kind of preparation method of isoflavone compound Download PDF

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CN110283182A
CN110283182A CN201910556847.0A CN201910556847A CN110283182A CN 110283182 A CN110283182 A CN 110283182A CN 201910556847 A CN201910556847 A CN 201910556847A CN 110283182 A CN110283182 A CN 110283182A
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volume ratio
concentrated
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白卫滨
蓝平
蒋鑫炜
孙建霞
田灵敏
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Jinan University
University of Jinan
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Abstract

The invention belongs to pharmaceutical technology fields, specifically disclose a kind of preparation method of isoflavone compound.The structure of the compound is as shown in formula I and formula II.Preparation method of the present invention is equal for raw material with siskin isoflavonoid 2, and isoflavone compound is prepared by the chemical reaction of five steps, the preparation method simple process, reaction condition more temperature, and final product yield is high, with high purity.

Description

A kind of preparation method of isoflavone compound
Technical field
The present invention relates to biomedicine technical fields, and in particular, to a kind of preparation method of isoflavone compound.
Background technique
Primary bronchogenic carcinoma of lung (abbreviation lung cancer) is the highest malignant tumour of disease incidence in recent years, and on its disease incidence Lifting speed is in first of various tumours.Lung cancer includes non-small cell lung cancer (NSCLC) and Small Cell Lung Cancer, is American male and female Property diagnosis in the second largest common cancer, the 14% of Zhan Suoyou new cancer.In China, lung cancer is most common in male's diagnosis The most cancer of number, accounts for the 23.03% and 16.2% of all new cases respectively in cancer and women diagnosis.Although lung The treatment means of cancer are maked rapid progress, but 5 years survival rates only 14.1%, and 60% patient is dead in diagnosis 1 year.Therefore compel to be essential Want new effective anti-lung-cancer medicament.
Isoflavones is cyclized after being extended by cinnamoyl coacetylase side chain in plant phenylalanine metabolic process, is formed with benzene color Phenolic compound based on ketone ring, 3- phenyl derivatives are isoflavones.Isoflavone compound is because of its unique chemistry Structure and to mammalian cell have many important physiology, biochemical action.On the one hand, isoflavone compound has higher Chemical reactivity, experiment it has been confirmed that: they can remove free radical excessive in organism, have antioxidation；It is another Aspect, isoflavone compound have many important pharmacological actions again, have therapeutic effect to many diseases of the mankind.Research Isoflavone compound is of great significance to the antitumor and cardiovascular disease of the mankind.Therefore, isoflavone compound causes The extensive attention of domestic and international pharmacy men has very tempting application prospect.
But most of isoflavone compound is all plant origin, chemical production processes are less, and there is The problems such as difficulty is big, reaction process is complicated, the yield of severe reaction conditions, product and purity are told somebody what one's real intentions are can not simply carry out big Prepared by batch, constrain the application of isoflavone compound.
Summary of the invention
The purpose of the invention is to overcome the above-mentioned deficiency of the prior art, a kind of preparation of isoflavone compound is provided Method.The preparation method simple process, reaction condition more temperature, final product yield are high, with high purity.
To achieve the goals above, the present invention is achieved by following scheme:
A kind of preparation method of isoflavone compound, the structure of the compound is as shown in formula I and formula II:
Its preparation process includes the following steps:
S1. it is that 4:300 is dissolved in methanol by mass volume ratio by siskin isoflavonoid 2, adds 3- methyl-2-butene Aldehyde, calcium hydroxide are concentrated after being stirred to react 45~50h in 18~20 DEG C；Gained head product is dissolved in ethyl acetate, with 1M's Hydrochloric acid water dissolution washing；Organic phase is separated, with filtering after anhydrous sodium sulfate drying, filtrate is concentrated to get crude product；Petroleum is used again Ether and ethyl acetate carry out silica gel column chromatography purifying to crude product, obtain intermediate 3；
S2. it is that 1.1:10 is dissolved in dry methylene chloride by mass volume ratio by intermediate 3, adds pyridine, acetic acid Acid anhydride is concentrated after 18~20 DEG C of 5~7h of reaction；Gained head product is dissolved in ethyl acetate, crosses chromatographic column and chromatographic solution is concentrated, Obtain product 4；
S3. product 4 is dissolved in dry tetrahydrofuran, triphenylphosphine and diethyl azodiformate is added at 0 DEG C, Geraniol or 3- methyl-2 butenol, reaction solution are gradually heated to 18~20 DEG C, are concentrated after reacting 5~7h；Gained head product is molten Solution crosses chromatographic column and chromatographic solution is concentrated, obtain product 5 in petrol ether/ethyl acetate mixed solution；
S4. product 5 is dissolved in dry chloroform, (6,6,7,7,8,8,8- seven fluoro- 2, the 2- dimethyl-of 0.7g tri- is added 3,5- acetyl caproyl europiums, reaction solution are concentrated after being heated to reflux 6h；Gained crude product petroleum ether and ethyl acetate carry out silica gel column layer Analysis purifying, obtains intermediate 6；
S5. intermediate 6 is dissolved in tetrahydrofuran/methanol mixed solution, potassium carbonate is added at 0 DEG C, after reacting 3h Concentration；Gained head product petroleum ether and ethyl acetate carry out silica gel column chromatography and purify, and obtain osajin shown in formula I or formula II Compound；
Wherein, the mass volume ratio of siskin isoflavonoid 2 described in step S1 and 3- methyl-2-butene aldehyde be 4:(14~ 15), the mass ratio of siskin isoflavonoid 2 and calcium hydroxide is 1:(1~1.5)；
The mass volume ratio of intermediate 3 described in step S2 and pyridine is 33:8, the quality volume of intermediate 3 and acetic anhydride Than for 110:31；
The mass volume ratio of triphenylphosphine described in step S3 and geraniol or 3- methyl-2 butenol is 7.7:5, triphen The mass volume ratio of base phosphine and diethyl azodiformate is 7.7:4.62；Stone in the petrol ether/ethyl acetate mixed solution The volume ratio of oily ether and ethyl acetate is 10:1；
Intermediate 6 described in step S5 and tetrahydrofuran/methanol mixed solution mass volume ratio are 1:200, intermediate 6 Mass ratio with potassium carbonate is 15:4；The volume ratio of tetrahydrofuran and methanol is 1 in the tetrahydrofuran/methanol mixed solution: 2。
Preferably, the mass volume ratio of siskin isoflavonoid 2 described in step S1 and 3- methyl-2-butene aldehyde is 4:14.4, The mass ratio of siskin isoflavonoid 2 and calcium hydroxide is 1:1.1.
Preferably, the condition being stirred to react described in step S1 is to react 48h at 18 DEG C.
Preferably, the condition of reaction described in step S2 is to react 6h at 18 DEG C.
Preferably, the condition of reaction described in step S3 is to react 6h at 18 DEG C.
Compared with prior art, the invention has the following advantages:
Preparation method of the invention is equal for raw material with siskin isoflavonoid 2, and isoflavones is prepared by the chemical reaction of five steps Class compound Final-2, the preparation method simple process, reaction condition more temperature, final product yield are high, with high purity.
Detailed description of the invention
Fig. 1 is the hydrogen spectrogram of intermediate 3 in Examples 1 and 2.
Fig. 2 is the carbon spectrogram of intermediate 3 in Examples 1 and 2.
Fig. 3 is the mass spectrogram of osajin drug Final-2.
Fig. 4 is the carbon spectrogram of osajin drug Final-2.
Fig. 5 is the hydrogen spectrogram of osajin drug Final-2.
Fig. 6 is the hydrogen spectrogram of intermediate 6 in embodiment 2.
Fig. 7 is the carbon spectrogram of intermediate 6 in embodiment 2.
Fig. 8 is the hydrogen spectrogram of climbing trifoliate jewelvine isoflavones prepared by embodiment 2.
Fig. 9 is the carbon spectrogram of climbing trifoliate jewelvine isoflavones prepared by embodiment 2.
Specific embodiment
With reference to the accompanying drawings of the specification and specific embodiment is made the present invention and is further elaborated, the embodiment It is served only for explaining the present invention, be not intended to limit the scope of the present invention.Test method as used in the following examples is such as without spy Different explanation, is conventional method；Used material, reagent etc., unless otherwise specified, for the reagent commercially obtained And material.
The preparation of 1 isoflavone compound Final-2 of embodiment
The route processed of isoflavone compound Final-2 is as follows:
Final-2 is prepared by the chemical reaction of five steps, specifically comprises the following steps:
1, the preparation of intermediate 3
Siskin isoflavonoid 2 (4.0g, 29.6mmol) is dissolved in 300mL methanol, 3- methyl-2-butene aldehyde is added (14.4mL, 148.0mmol) and calcium hydroxide (4.4g, 59.2mmol).Reaction solution is dense after (18 DEG C) stirring 48h at room temperature Contracting, gained sample are dissolved in 300mL ethyl acetate and are dissolved with the hydrochloric acid water of 1M and washed.Organic phase is separated, anhydrous slufuric acid is used It is filtered after sodium is dry, filtrate is concentrated to get crude product.Silica gel column chromatography is carried out to crude product with petroleum ether and ethyl acetate to purify, Obtain 3.8g intermediate 3, yellow solid, yield 38%.
2, the preparation of intermediate 6
(1) intermediate 3 (6.6g, 19.6mmol) is dissolved in 60mL dry methylene chloride, addition pyridine (1.6mL, 19.6mmol) and acetic anhydride (1.86mL, 19.6mmol).Reaction solution is concentrated after (18 DEG C) stirring 6h at room temperature, gained primiparity Object is dissolved in 200mL ethyl acetate quickly through silicagel column, is obtained the higher product 4 of purity after chromatographic solution concentration and is directly thrown Enter the next step.
(2) yellow oil obtained by previous step is dissolved in 60mL dry tetrahydrofuran, triphenylphosphine is added at 0 DEG C (7.7g, 29.4mmol), geraniol (5.0mL, 29.4mmol) and diethyl azodiformate (4.62mL, 29.4mmol). Reaction solution is gradually heated to room temperature (18 DEG C), and reaction solution is concentrated after 6h, gained yellow oil be dissolved in 400mL petroleum ether/ In ethyl acetate mixture (volume ratio 10:1), quickly through silicagel column, the higher product 5 of purity is obtained after chromatographic solution concentration And direct plunge into the next step.
(3) yellow oil obtained by previous step is dissolved in the dry chloroform of 60mL, is added three (6,6,7,7,8,8,8- seven Fluoro- 2,2- dimethyl -3,5- acetyl caproyl europium (0.7g).Reaction solution is concentrated after being heated to reflux 6h, with petroleum ether and ethyl acetate pair Crude product carries out silica gel column chromatography purifying, obtains 4.5g intermediate 6, yellow solid, and three steps merge yield 45%.
3, the preparation of Final-2
Compound 6 (4.5g, 8.74mmol) is dissolved in 90mL tetrahydrofuran/methanol mixed solution (volume ratio 1:2), Potassium carbonate (1.2g, 8.74mmol) is added at 0 DEG C, is concentrated after reacting 3h.Gained head product petroleum ether and ethyl acetate pair Crude product carries out silica gel column chromatography purifying, obtains 2.0g Final-2, yellow solid, yield 48%.
Gained yellow solid Final-2 obtains its chemical structure, such as formula (I) institute through Mass Spectrometric Identification, carbon spectrum, hydrogen spectrum analysis Show, be (Z) -10- (3,7-dimethylocta-2,6-dien-l-yl) -5-hydroxy-7- (4-hydroxyphenyl) -2, 2-dimethyl-2H, 6H-pyrano [3,2-g] chromen-6-one, i.e. 8- geranyl timothy grass isoflavones.
The preparation of the climbing trifoliate jewelvine isoflavones of embodiment 2
The preparation route for climbing trifoliate jewelvine isoflavones is as follows:
It is prepared by the chemical reaction of five steps and climbs trifoliate jewelvine isoflavones, specifically comprised the following steps:
1, (5- hydroxyl -7- (4- hydroxy phenyl) -2,2- dimethyl -2H, 6H- pyrans simultaneously [3,2-g] chromene -6- of intermediate 3 Ketone) preparation
Siskin isoflavonoid 2 (4.0g, 29.6mmol), 3- methyl-2-butene aldehyde are sequentially added in 300mL methanol (14.4mL, 148.0mmol) and calcium hydroxide (4.4g, 59.2mmol) reacts 48 hours at room temperature.It is concentrated under reduced pressure, then 300mL ethyl acetate is added thereto, and with the salt acid elution of 1M.Organic phase is separated, filters, is concentrated after anhydrous sodium sulfate is dry Filtrate obtains crude product, and silica gel column chromatography is further purified, and obtains yellow solid compound 3 (3.8g, 11.3mmol), yield 38%.
1H NMR(500MHz,CDCl3) δ 13.12 (s, 1H), 7.82 (s, 1H), 7.38 (d, J=8.5Hz, 2H), 6.88 (d, J=8.5Hz, 2H), 6.73 (d, J=10.0Hz, 1H), 6.33 (s, 1H), 5.62 (d, J=10.0Hz, 1H), 1.47 (s, 6H).13C NMR(125MHz,CDCl3)δ180.94,159.55,157.31,156.86,155.90,152.56,130.33, 128.19,123.52,123.04,115.59,115.46,106.10,105.60,94.88,78.07,28.30.IR(KBr): νmax 3382,2976,2931,1652,1617,1572,1514,1462,1362,1246,1212,1175,1133,1062, 836cm-1.MS (ESI ,+ve): m/z 695 (30%), 475 (10), 359 ([M+Na]+,100),187(15).HRMS[M+Na]+ Calcd for C20H16O5 23Na:359.0895.Found:359.0891.
2, (4- (7- (2,2- dimethyl -5- ((3- methyl -2- alkene butyl) oxygroup) -6- oxo -2H, 6H- pyrrole of intermediate 5 Mutter simultaneously [3,2-g] chromene base)) phenylacetate) preparation
(1) compound 3 (3.3g, 9.8mmol), pyridine (0.8mL, 9.8mmol) are sequentially added in 40mL methylene chloride And acetic anhydride (0.93mL, 9.8mmol).It stirs 6 hours at room temperature.It being concentrated under reduced pressure, filtering, silica gel column chromatography is further purified, Obtain compound 4.
(2) 50mL dry tetrahydrofuran, triphen is added in yellow oil obtained by a step upwards in turn under zero degrees celsius Base phosphine (3.9g, 14.9mmol), 3- methyl-2 butenol (1.5mL, 14.9mmol) and diethyl azodiformate (2.3mL, 14.9mmol) reacts 6 hours under room temperature.Vacuum distillation removes solvent, and silica gel column chromatography is further purified, and obtains Huang Color solid chemical compound 5 (2.8g, 6.28mmol), it is 64% that two steps, which merge yield,.
3, (4- (7- (5- hydroxyl -2,2- dimethyl -10- (3- methyl-2-butene base) -6- oxo -2H, 6H- of intermediate 6 Pyrans simultaneously [3,2-g] chromene base)) phenylacetate) preparation
In the dry chloroform of 30mL, sequentially add that compound 5 (2.5g, 5.6mmol), three (6,6,7,7,8,8,8- seven is fluoro- 2,2- dimethyl -3,5- acetyl caproyl europiums (0.7g), reaction solution are heated to reflux 6 hours.It being concentrated under reduced pressure, column chromatography is further purified, Obtain yellow solid 6 (2.0g, 4.48mmol), yield 80%.
1H NMR(400MHz,CDCl3) δ 13.01 (s, 1H), 7.93 (s, 1H), 7.56 (d, J=8.5Hz, 2H), 7.18 (d, J=8.5Hz, 2H), 6.74 (d, J=10.0Hz, 1H), 5.63 (d, J=10.0Hz, 1H), 5.18 (m, 1H), 3.40 (d, J =7.3Hz, 2H), 2.32 (s, 3H), 1.82 (s, 3H), 1.69 (s, 3H), 1.47 (s, 6H)13C NMR(100MHz,CDCl3)δ 180.84,169.39,157.01,154.90,154.62,153.01,150.69,131.73,130.00,128.62,128.08, 122.70,121.88,121.75,115.79,107.54,105.85,105.54,77.85,28.20,25.75,21.27, 21.14,17.88.IR(KBr):νmax 2980,2885,1765,1654,1581,1507,1464,1366,1243,1200, 1167,1119,1076,910cm-1.MS(ESI,+ve):m/z 469([M+Na]+, 100%), 427 (40), 405 (10) .HRMS [M+Na]+Calcd for C27H26O6 23Na:469.1627.Found:469.1624.
4, the preparation of trifoliate jewelvine isoflavones is climbed
Under zero degrees celsius successively to 30mL tetrahydrofuran/methanol mixed solution (volume ratio 1:2), 6 (1.5g, 3.4mmol), potassium carbonate (0.47g, 3.4mmol) reacts 1 hour.Vacuum distillation removes solvent, and silica gel column chromatography is further pure Change, obtains yellow solid and climb trifoliate jewelvine isoflavones 1 (1.0g, 2.48mmol), yield 75%.
1H NMR(400MHz,CDCl3) δ 13.02 (s, 1H), 7.89 (s, 1H), 7.33 (d, J=8.6Hz, 2H), 6.81 (d, J=8.6Hz, 2H), 6.74 (d, J=10.0Hz, 1H), 5.78 (br s, 1H), 5.63 (d, J=10.0Hz, 1H), 5.18 (m, 1H), 3.40 (d, J=7.3Hz, 2H), 1.81 (s, 3H), 1.68 (s, 3H), 1.47 (s, 6H)13C NMR(100MHz, CDCl3)δ181.30,156.93,155.82,154.87,154.73,152.60,131.69,130.33,128.03,123.21, 121.95,115.84,115.59,107.47,105.90,105.46,77.82,28.21,25.77,21.29,17.89.IR (KBr):νmax 3658,3386,2977,2888,1652,1615,1573,1514,1462,1436,1382,1294,1205, 1176,1120,954,834cm-1.MS (ESI ,+ve): m/z 701 (50%), 427 ([M+Na]+,100),405([M+H]+, 20),217(20),187(25).HRMS[M+Na]+Calcd for C25H24O5 23Na:427.1521.Found:427.1503.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than protects to the present invention The limitation of shield range can also be made on the basis of above description and thinking for those of ordinary skill in the art Other various forms of variations or variation, there is no necessity and possibility to exhaust all the enbodiments.It is all of the invention Made any modifications, equivalent replacements, and improvements etc., should be included in the protection of the claims in the present invention within spirit and principle Within the scope of.

Claims (5)

1. a kind of preparation method of isoflavone compound, which is characterized in that II institute of the structure of the compound such as formula I and formula Show:
Its preparation process includes the following steps:
S1. it is that 4:300 is dissolved in methanol by mass volume ratio by siskin isoflavonoid 2, adds 3- methyl-2-butene aldehyde, hydrogen Calcium oxide is concentrated after being stirred to react 45~50h in 18~20 DEG C；Gained head product is dissolved in ethyl acetate, with the hydrochloric acid of 1 M Water dissolution washing；Organic phase is separated, with filtering after anhydrous sodium sulfate drying, filtrate is concentrated to get crude product；Again with petroleum ether and Ethyl acetate carries out silica gel column chromatography purifying to crude product, obtains intermediate 3；
S2. it is that 1.1:10 is dissolved in dry methylene chloride by mass volume ratio by intermediate 3, adds pyridine, acetic anhydride, in It is concentrated after 18~20 DEG C of 5~7h of reaction；Gained head product is dissolved in ethyl acetate, crosses chromatographic column and chromatographic solution is concentrated, must produce Object 4；
S3. product 4 is dissolved in dry tetrahydrofuran, triphenylphosphine and diethyl azodiformate is added at 0 DEG C, it is fragrant Leaf-alcohol or 3- methyl-2 butenol, reaction solution are gradually heated to 18~20 DEG C, are concentrated after reacting 5~7h；The dissolution of gained head product In petrol ether/ethyl acetate mixed solution, crosses chromatographic column and chromatographic solution is concentrated, obtain product 5；
S4. product 5 is dissolved in dry chloroform, three (6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl -3,5- pungent two is added Ketone europium, reaction solution are concentrated after being heated to reflux 6h；Gained crude product petroleum ether and ethyl acetate carry out silica gel column chromatography and purify, and obtain Intermediate 6；
S5. intermediate 6 is dissolved in tetrahydrofuran/methanol mixed solution, potassium carbonate is added at 0 DEG C, be concentrated after reacting 3h； Gained head product petroleum ether and ethyl acetate carry out silica gel column chromatography and purify to get osajin shown in formula I or formula II Close object；
Wherein, the mass volume ratio of siskin isoflavonoid 2 described in step S1 and 3- methyl-2-butene aldehyde is 4:(14~15), gold The mass ratio of sparrow isoflavones 2 and calcium hydroxide is 1:(1~1.5)；
The mass volume ratio of intermediate 3 described in step S2 and pyridine is 33:8, and intermediate 3 and the mass volume ratio of acetic anhydride are 110:31；
The mass volume ratio of triphenylphosphine described in step S3 and geraniol or 3- methyl-2 butenol is 7.7:5, triphenylphosphine Mass volume ratio with diethyl azodiformate is 7.7:4.62；Petroleum ether in the petrol ether/ethyl acetate mixed solution Volume ratio with ethyl acetate is 10:1；
Intermediate 6 described in step S5 and tetrahydrofuran/methanol mixed solution mass volume ratio are 1:200, intermediate 6 and carbon The mass ratio of sour potassium is 15:4；The volume ratio of tetrahydrofuran and methanol is 1:2 in the tetrahydrofuran/methanol mixed solution.
2. preparation method according to claim 1, which is characterized in that siskin isoflavonoid 2 described in step S1 and 3- methyl -2- The mass volume ratio of crotonaldehyde is 4:14.4, and the mass ratio of siskin isoflavonoid 2 and calcium hydroxide is 1:1.1.
3. preparation method according to claim 1, which is characterized in that the condition being stirred to react described in step S1 is at 18 DEG C React 48h.
4. preparation method according to claim 1, which is characterized in that the condition of reaction described in step S2 is to react at 18 DEG C 6h。
5. preparation method according to claim 1, which is characterized in that the condition of reaction described in step S3 is to react at 18 DEG C 6h。
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