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A kind of 2,3-dihydrobenzofuran derivative and its preparation and application

A derivative, dihydrobenzene technology, applied in 2 fields, can solve problems such as many side effects, psychotic episodes, liver toxicity, etc., and achieve the effects of easy industrialization, simple synthesis process, and high yield

Active Publication Date: 2011-12-07
徐州博创建设发展集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in addition to inhibiting monoamine oxidase, these drugs also have inhibitory effects on liver drug-metabolizing enzymes. They have many side effects, can produce central excitement, induce psychosis, have liver toxicity, and cause orthostatic hypotension.

Method used

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  • A kind of 2,3-dihydrobenzofuran derivative and its preparation and application
  • A kind of 2,3-dihydrobenzofuran derivative and its preparation and application
  • A kind of 2,3-dihydrobenzofuran derivative and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Preparation of 2-phenylselenylmethyl-4-hydroxy-5,7-dibenzoyl-2,3-dihydrobenzofuran (II)

[0051] The reaction formula is as follows:

[0052]

[0053] Under a nitrogen atmosphere, 7.16g (20mmol) of compound (II-2) was dissolved in 100mL of chloroform, and 4.96g (21mmol) of phenylselenium bromide (II-1), 2.80mL (20mmol) of triethylamine were added, Refluxing reaction for 5 hours, TLC detection compound (II-2) spot disappears, the reaction is complete, add 100mL saturated saline to separate layers, wash the organic phase with water 80mL×3, add anhydrous magnesium sulfate to dry, concentrate, and use petroleum ether and dichloro Methane (100:1) was recrystallized to obtain 9.234 g of white solid 2-phenylselenylmethyl-4-hydroxyl-5,7-dibenzoyl-2,3-dihydrobenzofuran (II), the yield 90%.

[0054] 1 H-NMR (CDCl 3 ): δ12.70(s, 1H), 7.78(s, 1H), 7.66-7.64(m, 2H), 7.54-7.534(m, 2H), 7.44-7.414(m, 4H), 7.36-7.30(m , 4H), 7.15-7.14(m, 3H), 5.06-5.03(m, 1H), 3.34-3....

Embodiment 2

[0056] Example 2: Preparation of 2-phenylselenylmethyl-4-propargyloxy-5,7-dibenzoyl-2,3-dihydrobenzofuran (IV)

[0057] The reaction formula is as follows:

[0058]

[0059] Under a nitrogen atmosphere, 5.12 g (10 mmol) of 2-phenylselenylmethyl-4-hydroxyl-5,7-dibenzoyl-2,3-dihydrobenzofuran (II) prepared in Example 1 ) was dissolved in 60mL acetone, added 1.4mL (15mmol) propargyl bromide (III), 2.1g (15mmol) potassium carbonate, reflux reaction for 5.0 hours, TLC tracking reaction, 2-phenylselenylmethyl-4-hydroxyl- The point of 5,7-dibenzoyl-2,3-dihydrobenzofuran (II) basically disappeared, the reaction was complete, the acetone was distilled off, extracted with 100mL dichloromethane, the organic phase was washed 3 times with saturated saline, and then Dry over anhydrous magnesium sulfate, concentrate, recrystallize the concentrate with a mixture of petroleum ether and dichloromethane (volume ratio: 100:1), filter, and dry to obtain 5.4 g of a white solid, namely 2-phenyls...

Embodiment 3

[0062] Example 3: 2-phenylselenylmethyl-4-(3-p-tolyl-isoxazol-5-ylmethoxy)-5,7-dibenzoyl-2,3-dihydrobenzene Preparation of furan (I-1)

[0063] The reaction formula is as follows:

[0064]

[0065] First, dissolve 0.540g (4.0mmol) 4-methylbenzaldehyde oxime (V-1) and 0.534g (4.0mmol) NCS in 30mL dichloromethane, and react at 30°C for 5 hours; under a nitrogen atmosphere, add 1.655 g (3.0mmol) 2-phenylselenylmethyl-4-propargyloxy-5,7-dibenzoyl-2,3-dihydrobenzofuran (IV) prepared by the method in Example 2, 2.0 hours 0.70mL triethylamine (5mmol, dissolved with 5mL dichloromethane) was added dropwise thereto, and then incubated at 30°C for 8 hours, the compound point shown in TLC (IV) disappeared and the reaction was complete, extracted with 40mL dichloromethane, organic Add 60mL of saturated saline solution to wash twice, then dry with anhydrous magnesium sulfate, concentrate, and the concentrate is passed through a chromatographic column (eluent is V 石油醚 :V 乙酸乙酯 =1:5), 1...

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Abstract

The invention discloses 2,3-dihydrobenzofuran derivatives shown in a formula (I), intermediates for preparing the derivatives and a preparation method of the derivatives. In the formula (I), R1 is shown in formulae (II) and (III), wherein R5 and R6 are independently substituted phenyl; R2 and R4 are independently benzoyl or substituted benzoyl; and R3 is H, hydroxy, halogen, nitro or C1-C3 alkyl. In the invention, novel 2-phenylseleno-methyl-2,3-dihydrobenzofuran compounds containing organic selenium and five-membered nitrogen-containing heterocycles are provided; the synthesis process is simple, is high in yield and is easy to industrialize; and the compounds are depressant medicaments with significant inhibition on monoamine oxidase activity, thereby providing a research basis for screening new medicaments such as antidepressant medicaments, anti-Parkinson medicaments and the like.

Description

(1) Technical field [0001] The invention relates to a 2,3-dihydrobenzofuran derivative containing organic selenium and a five-membered nitrogen heterocycle, in particular to a 2-phenylselenylmethyl 2,3-dihydrobenzofuran derivative and Its preparation and application. (2) Background technology [0002] Monoamine oxidase (monoamine oxidase) is an enzyme that catalyzes the oxidative deamination reaction of monoamine. The abbreviation MAO is also called flavin-containing amine oxidase, which can promote the oxidation of amine substrates into corresponding imines, and the imines are then hydrolyzed into aldehyde products. These enzymes play an important role in the central nervous system, maintaining the homeostasis of nerve ending transmission, such as dopamine and serotonin in the blood, as well as amines produced by the metabolism of food and drugs in the periphery. Many neurological and mental diseases are related to changes in MAO levels. Studies have shown that increased ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D405/12C07D307/79A61K31/422A61K31/4192A61P25/24A61P25/16
Inventor 王宇光
Owner 徐州博创建设发展集团有限公司
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