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Compound containing structure of o-naphthaquinone and application

A technology of a compound, o-naphthoquinone, which is applied in the field of pharmaceutical compounds and its preparation, can solve problems such as unsatisfactory effects, and achieve the effect of using a small dosage

Inactive Publication Date: 2007-05-30
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cryptotanshinone and dihydrotanshinone I have been used in our laboratory for anti-hyperammonia and the treatment of hepatic encephalopathy and subclinical hepatic encephalopathy caused by hyperammonemia, and have applied for a patent (PCT / CN01 / 00861) , but its effect is not very satisfactory

Method used

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  • Compound containing structure of o-naphthaquinone and application
  • Compound containing structure of o-naphthaquinone and application
  • Compound containing structure of o-naphthaquinone and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of 3-methyl-3-hydroxy-9-chloro-2,3-dihydronaphtho[1,8-b,c]pyran-7,8-dione:

[0044] Compound 9-chloronaphtho[1,8-b,c]pyran-3(2H)-one 7g was dissolved in 200ml of anhydrous ether, and the anhydrous ether of Grignard reagent MeMgI (100-150mmol) prepared in advance Put 70ml of the solution in a dropping funnel, add it in a water bath for 1.5-2 hours, stir at room temperature for 30 minutes, pour the reaction solution into 250ml of ice water solution, extract with chloroform, wash with water, dry over anhydrous sodium sulfate, and concentrate to obtain a brown-red viscous liquid 6.4g. Dissolve 6.4g of the product in 80-100ml of acetic anhydride, quickly add 8.5g of copper nitrate trihydrate, stir at room temperature for 15 minutes, add ice water to terminate the reaction, extract with ether, wash with aqueous sodium carbonate solution, then wash with water, anhydrous sodium sulfate Drying, concentration, silica gel column separation and purification, and chloro...

Embodiment 2

[0070] Preparation of 3-methyl-3-hydroxy-9-bromo-2,3-dihydronaphtho[1,8-b,c]pyran-7,8-dione:

[0071] Adopt 9-bromonaphtho[1,8-b,c]pyran-3(2H)-one as raw material, adopt the same method as Example 1, just adopt Na 2 S 2 o 4 As a reducing agent, 3-methyl-9-bromonaphtho[1,8-b,c]pyran-7,8-dione can be obtained.

[0072] Adopting 9-bromonaphtho[1,8-b,c]pyran-3(2H)-ketone is that raw material reacts with different Grignard reagents, adopts the method identical with embodiment 1 and 2 to also can obtain:

[0073] 1. 3-Propyl-3-hydroxy-9-bromo-2,3 dihydronaphtho[1,8-b,c]pyran-7,8-dione

[0074] 2. 3-Hexyl-3-hydroxy-9-bromo-2,3 dihydronaphtho[1,8-b,c]pyran-7,8-dione

[0075] 3. 3-allyl-3-hydroxy-9-bromo-2,3 dihydronaphtho[1,8-b,c]pyran-7,8-dione

Embodiment 3

[0077] Preparation of 3-methyl-9-chloro-2,3-dihydronaphtho[1,8-b,c]pyran-7,8-dione:

[0078] Using the compound 9-chloronaphtho[1,8-b,c]pyran-3(2H)-one as raw material, adopt a method similar to that of Example 1, except that 9-chloro-3-methyl-2, The one-step nitration reaction time of 3-dihydronaphtho[1,8-b,c]pyran-3-ol with acetic anhydride and copper nitrate trihydrate was extended to 1 hour to obtain 9-chloro-7-nitro-3 -Methyl-2,3-dihydronaphtho[1,8-b,c]pyran-3-ol acetate, other operations are the same as in Example 1, and finally obtain orange-red solid 3-methyl-9 -Chloro-2,3-dihydronaphtho[1,8-b,c]pyran-7,8-dione.

[0079] In the same way, you can also get:

[0080] 3-Propyl-9-chloro-2,3-dihydronaphtho[1,8-b,c]pyran-7,8-dione

[0081] 3-Benzyl-9-chloro-2,3-dihydronaphtho[1,8-b,c]pyran-7,8-dione

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Abstract

A compound containing o-naphthalene quinone structure for preparing medicines to prevent and treat hyperammonemia and hepatic encephalopathy is prepared from natural Masonate F through structure reformation and optimization.

Description

technical field [0001] The invention relates to the field of pharmaceutical compounds, in particular to a pharmaceutical compound and its preparation method and application. Background technique [0002] Hepatic encephalopathy (Hepatic encephalopathy, referred to as HE) is mainly caused by severe liver function disorders or disorders, and is a central nervous system dysfunction syndrome characterized by metabolic disorders (Pathology, edited by Li Yulin, People's Health Publishing House, 2000, p340 -350). Mild HE, also known as subclinical hepatic encephalopathy, most patients have no disturbance of consciousness, work and life are no different from ordinary people, and feel basically good about themselves. Due to the lack of clinical symptoms, it is easy to be ignored by others, and even they cannot be aware of it. But all there are deficiencies in learning, operation, understanding, abilities such as strain and sleep, quality of life. If you engage in delicate work such ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/92A61K31/352A61P3/00A61P1/16A61P25/00
Inventor 古练权黄世亮黄志纾陈新滋李月明卜宪章
Owner SUN YAT SEN UNIV
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