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Synthetic method for polysubstituted baicalein derivatives

A kind of derivative, baicalein technology, applied in the field of organic synthesis

Inactive Publication Date: 2015-04-22
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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  • Synthetic method for polysubstituted baicalein derivatives
  • Synthetic method for polysubstituted baicalein derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1: 4'-methyl-5,6,7-trimethoxybaicalein

[0014] 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%).

[0015] 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%).

[0016] 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 precipitates. Filter and wash the precipitate with eth...

Embodiment 2

[0018] Example 2: Preparation of 4', 5, 6, 7-tetramethoxybaicalein

[0019] 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.

[0020] 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 distilled off under reduced pressure to...

Embodiment 3

[0023] Example 3: Preparation of 3', 5, 6, 7-tetramethoxybaicalein

[0024] 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%).

[0025] 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%).

[0026] 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 to room temperature and precipitated. Filtration, the...

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Abstract

The invention discloses a synthetic method for a kind of polysubstituted baicalein derivatives shown as a formula I, and in the formula I, R1, R2 and R3 are H, hydroxyl, alkyl, alkoxy and the like. By modifying baicalein B-ring skeleton, the baicalein derivatives are synthesized, which are substantially improved in dissolvability, anticancer activity and other aspects compared with baicalein. The method employs substituted benzaldehyde and 3,4,5-trimethoxyphenol as basic raw materials, and the B-ring polysubstituted baicalein derivatives are prepared through 3 steps. The method concretely comprises performing condensation reaction on the substituted benzaldehyde and an acid anhydride under the effect of an alkali catalyst, so as to obtain substituted cinnamic acid, and further synthesizing substituted cinnamoyl chloride, performing acylation reaction on the substituted cinnamoyl chloride and 3,4,5-trimethoxyphenolunder the effect of a catalyst, so as to obtain a chalcone compound, and performing cyclization reaction on the chalcone compound under the effect of a catalyst, so as to obtain the corresponding polysubstituted baicalein derivative. The method is simple in technology, abundant in raw materials, high in yield, good in product purity and low in cost, and has wide application prospect.

Description

technical field [0001] The invention relates to a synthesis method of multi-substituted baicalein derivatives, belonging to the technical field of organic synthesis. 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] As reported in the literat...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 刘湘朱洁莲李炜
Owner JIANGNAN UNIV
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