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A kind of synthetic method of 3', 4', 7-trihydroxy isoflavone

A technology of trihydroxy isoflavone and trimethoxy isoflavone, applied in the field of pharmaceutical synthesis, can solve the problems of low conversion rate, harsh reaction conditions, difficult separation and purification, etc.

Active Publication Date: 2022-04-29
中国人民解放军联勤保障部队第九四〇医院
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  • Abstract
  • Description
  • 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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  • A kind of synthetic method of 3', 4', 7-trihydroxy isoflavone
  • A kind of synthetic method of 3', 4', 7-trihydroxy isoflavone
  • A kind of synthetic 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: 4′, 7-dimethoxyisoflavone and bromine are mixed and reacted in dichloromethane medium to obtain 3′-bromo-4′, 7-dimethoxyisoflavone, wherein, the 4 ', the molar ratio of 7-dimethoxyisoflavone and bromine is 1: 1.1~1.5, and the reaction temperature is 20~30°C; 3'-bromo-4', 7-dimethoxyisoflavone is Reaction with sodium methylate under the action of salt to obtain 3', 4', 7-trimethoxy isoflavone; 3', 4', 7-trimethoxy isoflavone demethylation to obtain the 3', 4', 7‑Trihydroxyisoflavone. Compared with the prior art, the present invention has abundant sources of starting materials, mild reaction conditions, good selectivity and high yield, and is suitable for industrialized 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 Patents(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