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Total synthesis preparation method of natural product flavonoid compounds

A technology of flavonoids and natural products, applied in the direction of drug combination, organic chemistry, anti-toxin, etc., to achieve the effect of easy reaction, stable intermediates and easy access to raw materials

Active Publication Date: 2016-10-05
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After consulting the literature, the relevant patent 201310309953.1 discloses a synthetic method of Morin (1), and there is no report on the total synthetic method of Sanggenol F (2) so far; Route design and synthetic method for the above-mentioned compounds in the prior art and with simple synthetic methods

Method used

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  • Total synthesis preparation method of natural product flavonoid compounds
  • Total synthesis preparation method of natural product flavonoid compounds
  • Total synthesis preparation method of natural product flavonoid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1 Synthetic 2-hydroxyl-4,6-dimethoxyacetophenone (4)

[0050] Weigh the substrate 2,4,6-trihydroxyacetophenone (10g, 59.50mmol) and K 2 CO 3 (16.5g, 119mmol) was placed in a 500mL eggplant-shaped bottle, added 150mL acetone and heated to reflux, and measured (CH 3 ) 2 SO 4 (3×3.76mL, 119mmol) was added into the reaction flask three times every two hours, and reacted for 6h. TLC monitoring (PE / EA 6:1) shows that raw material disappears substantially, in R f = 0.3 There is product formation. After filtration, the solvent was spun off to obtain 11.3 g of 4 as a light yellow solid, with a yield of 97%. mp 74-75℃.IR(neat):ν2970,2833,1617,1440,1157,895,597cm -1 . 1 H NMR (400MHz, CDCl 3 ):δ14.04(s,1H,OH),6.05(d,J=2.4Hz,1H,Ar-H),5.91(d,J=2.4Hz,1H,Ar-H),3.84(s,3H ,OCH 3 ),3.81(s,3H,OCH 3 ),2.60(s,3H,COCH 3 )...

Embodiment 2

[0051] Example 2 Synthesis of (E)-3-(2,4-dimethoxyphenyl)-1-(2-hydroxyl-4,6-dimethoxyphenyl)prop-2-en-1-one (5)

[0052] Weigh the above-mentioned 2-hydroxy-4,6-dimethoxyacetophenone (30mg, 0.15mmol) and 2,4-dimethoxybenzaldehyde (26mg, 0.15mmol) into a 10mL eggplant-shaped bottle, add 0.5 mL of ethanol was added dropwise to 50% aqueous KOH solution in an ice bath at 0°C, the ice bath was removed, and the reaction was carried out at room temperature for 2 days. TLC monitoring (PE / EA10:1) shows that raw material disappears substantially, in R f= 0.3 There is product formation. Adjust dilute hydrochloric acid to acidity, extract three times with ethyl acetate, wash three times with saturated sodium bicarbonate solution, three times with saturated brine, and dry over anhydrous sodium sulfate. Filtrate, spin off the solvent, and separate by column chromatography (PE / EA 10:1) to obtain 40 mg of 5 yellow solids with a yield of 76%. mp 132-133℃.IR(neat):ν2923,2366,1619,1219,1060,...

Embodiment 3

[0053] Example 3 Synthesis of 2-(2,4-dimethoxyphenyl)-3-hydroxyl-5,7-dimethoxy-4H-benzopyran-4-one (6)

[0054] Weigh substrate 5 (17mg, 0.05mmol) and dissolve in 0.25mL CH 3 OH (5mL / mmol), 0.16mL 5.4% NaOH aqueous solution (3.2mL / mmol) was added dropwise at 0°C in an ice bath, and then 0.02mL 30% H 2 o 2 (0.37 mL / mmol). The reaction solution was reacted at 0°C for 3h, and gradually raised to 40°C for 16h. TLC monitoring (PE / EA 1:1) shows that raw material disappears substantially, in R f = 0.23 there is product formation. Cool to room temperature, acidify with dilute hydrochloric acid, extract three times with ethyl acetate, wash three times with saturated aqueous sodium bicarbonate solution, three times with saturated brine, and dry over anhydrous sodium sulfate. Filtration, spin off the solvent, and column chromatography (PE / EA 1:1), the product 6 was obtained as light yellow solid 4mg, yield 23%. mp:156-157℃.IR(neat):ν3191,2920,1620,1412,1023,816,726cm -1 . 1 H NMR...

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Abstract

The invention belongs to the fields of organic synthesis and pharmaceutical chemistry, and relates to a total synthesis preparation method and an application of natural product flavonoid compounds. The method comprises the following steps: respectively carrying out a 4-step reaction and a 8-step reaction on 2,4,6-trihydroxyacetophenone used as a raw material to complete total synthesis of a natural product Morin (1); and respectively carrying out a 7-step reaction and a 9-step reaction on the Morin (1) used as a raw material to complete total synthesis of a natural product Sanggenol F (2). The method has the advantages of easily available raw materials, stable intermediate, mild conditions, easily controlled reaction, and important reference and utility values in massive production of the Morin and the Sanggenol F. The prepared Morin (1) can be used to prepare anti-oxidation drugs, anti-diabetes drugs, immunoloregulation drugs or antitumor drugs; and the prepared Sanggenol F can be used to prepare metabolic disease resisting drugs, and the metabolic disease resisting drugs are insulin sensitizers, blood sugar lowering drugs or blood fat lowering drugs.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicinal chemistry, and relates to a method for the total synthesis of natural product flavonoids and its application. The natural product flavonoids of the present invention include the natural flavonoid Morin (Morin) with a wide range of biological activities and the natural prenyl flavonoid Sanggenol F (Sanggenol F) with significant anti-metabolic disease activity . Background technique [0002] The prior art discloses relevant active natural flavonoids, especially Morin (Morin, 1) and Sanggenol F (Sanggenol F, 2) are important active natural flavonoids. Among them, Morin(1) has a wide range of biological activities, such as antioxidant effect (Subash, S.; Subramanian, P. Mol. Cell Biochem. 2009, 327, 153-161), anti-diabetic effect (Alkhamees, O.A.Br.J. Pharmacol.Toxicol.2013,4(1),10-17), immune regulation (Jakhar,R.; Paul,S.; Chauhan,A.K.; Kang,S.C.Int.Immunopharmacol.2014,22,356-365), ...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D493/04A61P3/10A61P39/06A61P37/02A61P35/00A61P3/00A61P3/06
Inventor 侯爱君王洋盛潇唐飞贾心语
Owner FUDAN UNIV
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