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Method for compounding baicalein derivative

A technology of baicalein and derivatives, applied in the field of drug synthesis

Inactive Publication Date: 2011-05-18
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few literature reports on the modification of the B-ring skeleton of baicalein to obtain stronger pharmacological effects

Method used

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  • Method for compounding baicalein derivative
  • Method for compounding baicalein derivative
  • Method for compounding baicalein derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: 4'-methyl-5,6,7-trimethoxybaicalein (compound of formula I, R is 4'-methyl)

[0017] Add 17mL (150mmol) p-tolualdehyde, 19mL (200mmol) acetic anhydride, 10g potassium carbonate to the flask, and heat to reflux for 1.5h. It was extracted with ethyl acetate (3×250 mL), the organic layer was dried over anhydrous sodium sulfate, concentrated, and recrystallized from ethanol to obtain p-methylcinnamic acid (20 g, 82%).

[0018] Add 16.3g (100mmol) p-methylcinnamic acid, 80mL CH 2 Cl 2 , at N 2 Under protection, use an ice-water bath to maintain the temperature at 0-5°C, and drop 9.5mL (130mmol) SOCl 2 And a small amount of anhydrous DMF, react at 0-5°C for 2h. The solvent was distilled off under reduced pressure to obtain p-methylcinnamoyl chloride (13.5 g, 82%).

[0019] In the flask, add 13g (80mmol) p-methylcinnamoyl chloride, 12.9g (70mmol) 3,4,5-trimethoxyphenol, 80mL BF 3 -Et 2 O, heated to reflux for 30min, cooled to room temperature to precipitate p...

Embodiment 2

[0021] Example 2: Preparation of 4', 5,6,7-tetramethoxybaicalein (compound of formula I, R is 4'-methoxy)

[0022] Add 18.2mL (150mmol) p-methoxybenzaldehyde, 19mL (200mmol) acetic anhydride, 8g anhydrous potassium acetate to the flask, and heat to reflux for 2h. Add 15g of sodium carbonate to make the solution slightly alkaline, carry out steam distillation until the distillate has no oil droplets, add an appropriate amount of activated carbon and boil for 5-10min, suction filter while it is hot, add 30mL of concentrated hydrochloric acid to the filtrate to make the solution obviously acidic , a large amount of solids were precipitated, and p-methoxycinnamic acid (23 g, 85%) was obtained by suction filtration.

[0023] Add 17.8g (100mmol) p-methoxycinnamic acid, 80mL CH 2 Cl 2 , at N 2 Under protection, use an ice-water bath to maintain the temperature at 0-5°C, and drop 9.5mL (130mmol) SOCl 2 And a small amount of anhydrous DMF, react at 0-5°C for 2.5h. The solvent was ...

Embodiment 3

[0026] Example 3: Preparation of 3', 5,6,7-tetramethoxybaicalein (compound of formula I, R is 3'-methoxy)

[0027] Add 18.2mL (150mmol) m-methoxybenzaldehyde, 19mL (200mmol) acetic anhydride, 8g anhydrous potassium acetate to the flask, and heat to reflux for 3h. It was extracted with ethyl acetate (3×250 mL), the organic layer was dried over anhydrous sodium sulfate, concentrated, and recrystallized from ethanol to obtain m-methoxycinnamic acid (21.4 g, 80%).

[0028] Add 17.8g (100mmol) m-methoxycinnamic acid, 80mL CH 2 Cl 2 , at N 2 Under protection, use an ice-water bath to maintain the temperature at 0-5°C, and drop 9.5mL (130mmol) SOCl 2 and a small amount of anhydrous DMF, and reacted at 0-5°C for 3h. The solvent was distilled off under reduced pressure to obtain m-methoxycinnamoyl chloride (17 g, 80%).

[0029] In the flask, add 16.1g (80mmol) m-methoxycinnamoyl chloride, 12.9g (70mmol) 3,4,5-trimethoxyphenol, 80mL BF 3 -Et 2 O, heated to reflux for 1h, cooled t...

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Abstract

The invention discloses a method for compounding a novel baicalein derivative as shown in a formula I, wherein R can be H, hydroxyl, alkyl, alkoxy, nitro and the like. By modifying a baicalein B-ring skeleton, the baicalein derivative which has greatly-improved dissolubility and anticancer activity and the like compared with baicalein is compounded. In the method, the B-ring substituted baicalein derivative is prepared by using benzaldehyde or substituted benzaldehyde and 3,4,5-trimethoxy-phenol as basic raw materials through four steps. The method comprises the detailed steps: the benzaldehyde or the substituted benzaldehyde is subjected to a condensation reaction with anhydride under the action of a basic catalyst to obtain substituted cinnamylate; the substituted cinnamylate is subjected to a halogenating reaction under the action of a catalyst to obtain substituted cinnamoyl chloride; the substituted cinnamoyl chloride is subjected to an acylation reaction with the 3,4,5-trimethoxy-phenol under the action of a catalyst to obtain a chalcone compound; and the chalcone compound is subjected to a ring-closure reaction under the action of a catalyst to obtain the baicalein derivative. The method has the advantages of simple process, rich raw materials, high yield, good product purity and low cost, and has broad application prospect. The formula I is shown in the specification.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of novel baicalein derivatives. Background technique [0002] Baicalein is the main active ingredient of traditional Chinese medicine Scutellaria baicalensis, which has antibacterial, antiviral, anti-inflammatory, antioxidative, scavenging oxygen free radicals, anticancer, antitumor, anticoagulant, antithrombosis and protection of liver, cardiovascular and cerebrovascular, neurons, etc. Various physiological activities and pharmacological effects, but the poor solubility of baicalein limits its application in the field of medicine. In order to improve these shortcomings and expand its application range, people have modified its structure and synthesized a series of baicalein derivatives. These derivatives have greater improvement than baicalein in terms of water solubility, fat solubility and anticancer. . [0003] According to literature reports (J.Med.Chem, ...

Claims

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Application Information

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IPC IPC(8): C07D311/74
Inventor 刘湘王晶王亿
Owner JIANGNAN UNIV
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