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Synthesis method of 3 ', 4', 7-trihydroxy isoflavone

A technology of trihydroxyisoflavone and trimethoxyisoflavone, which is applied in the field of drug synthesis, can solve problems such as low conversion rate, harsh reaction conditions, and difficult separation and purification, and achieve mild reaction conditions, easy industrial production, and high yield. Effect

Active Publication Date: 2020-08-25
中国人民解放军联勤保障部队第九四〇医院
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  • Claims
  • Application Information

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Problems solved by technology

However, the reaction conditions of these methods are harsh, the conversion rate is low, and separation and purification are difficult.

Method used

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  • Synthesis method of 3 ', 4', 7-trihydroxy isoflavone
  • Synthesis method of 3 ', 4', 7-trihydroxy isoflavone
  • Synthesis method of 3 ', 4', 7-trihydroxy isoflavone

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Embodiment 1

[0031] Preparation of 3',4',7-trihydroxyisoflavone

[0032]

[0033] Synthesis of 4′,7-dimethoxyisoflavone

[0034] Daidzein (20mmol, 5.08g) and potassium carbonate (40mmol, 5.52g) were suspended in 200mL of acetone, and 7.6mL of dimethyl sulfate (40mmol) was added to react at 60°C for 12h. TLC monitoring, after the reaction is complete, quench the reaction with 400 μL of 25% ammonia water, add 100 mL of water, and adjust the pH to be acidic with HCl, then remove the acetone under reduced pressure, wash with purified water until neutral after filtration, and dry to obtain 5.53 g of white powder, which is 4',7-Dimethoxyisoflavone, the yield is 98%.

[0035] Suspend formononetin (20mmol, 5.36g) and potassium carbonate (20mmol, 2.76g) in 200mL acetone, add 3.8mL dimethyl sulfate (20mmol), and react at 60°C for 12h. TLC monitoring, after the reaction is complete, quench the reaction with 400 μL of 25% ammonia water, add 100 mL of water, and adjust the pH to be acidic with HCl...

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Abstract

The invention discloses a synthesis method of 3', 4', 7-trihydroxy isoflavone. The method comprises the steps that 4', 7-dimethoxyisoflavone and bromine are subjected to a mixed reaction in a dichloromethane medium to obtain 3'-bromo-4 ', 7-dimethoxyisoflavone, wherein the molar ratio of 4', 7-dimethoxyisoflavone to bromine is 1: 1.1-1.5, and the reaction temperature is 20-30 DEG C; the 3'-bromo-4', 7-dimethoxyisoflavone reacts with sodium methoxide under the action of cuprous salt to obtain 3', 4', 7-trimethoxyisoflavone; and the 3', 4', 7-trimethoxyisoflavone is demethylated to obtain the 3', 4', 7-trihydroxy isoflavone. Compared with the prior art, the method has the advantages of abundant sources of initial raw materials, mild reaction conditions, high selectivity and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and specifically a method for synthesizing 3', 4', 7-trihydroxy isoflavones. Background technique [0002] Isoflavones are secondary metabolites of plants, which have a wide range of physiological activities such as anti-inflammation, anti-virus, anti-tumor, anti-diabetes, anti-radiation, anti-ischemia-reperfusion injury and neuroprotection, and most of these beneficial pharmacological effects Due to its excellent antioxidant activity, it is able to avoid oxidative damage by inhibiting and scavenging free radicals and reactive oxygen species (Nat. Prod. Rep, 2019, 36(8): 1156-1195). Studies have pointed out that the hydroxyl substituent in the isoflavone structure is an active group for scavenging free radicals, and the number, substitution position and substitution form of hydroxyl groups have an important impact on the activity (Int J Mol Sci, 2015, 16(6): 12891-12906) . [0003] 3', 4', 7-trihy...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36
CPCC07D311/36
Inventor 赵勇景临林邵瑾马慧萍赵彤
Owner 中国人民解放军联勤保障部队第九四〇医院