Di(7-hydrxyl-2,3-dihydro-1-1H-indeno)ether and the like, synthetic method and application

An analogue, dihydro technology, applied in the field of drug synthesis, can solve the problems of unsatisfactory effect of interferon hepatitis C, high production cost, long course of treatment, etc.

Inactive Publication Date: 2007-10-24
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] It can be seen that the effect of interferon in the treatment of hepatitis C is far from satisfactory, and has the disadvantages of obvious side effects, long course of treatment, high production cost, etc.

Method used

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  • Di(7-hydrxyl-2,3-dihydro-1-1H-indeno)ether and the like, synthetic method and application
  • Di(7-hydrxyl-2,3-dihydro-1-1H-indeno)ether and the like, synthetic method and application
  • Di(7-hydrxyl-2,3-dihydro-1-1H-indeno)ether and the like, synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: Starting from phenol to synthesize self-etherification product 1 (Scheme 1).

[0028]

[0029] Scheme 1.Synthesis of 1: (i) acryloyl chloride, Et 3 N, CH 2 Cl 2 , rt, 2h; (ii) AlCl 3 , 150-160°C, 6h, 15% (total yield of step i and ii); (iii) NaBH 4 / CH 3 OH, 75%; (iv) CH 2 Cl 2 , rt, one week, 35%.

Embodiment 2

[0031] Embodiment 2: the synthesis of phenol acrylate (3)

[0032] Phenol (1 g, 10.6 mmol) was dissolved in 5 mL of anhydrous CH 2 Cl 2 , cooled to 0°C in an ice-water bath, triethylamine (1.72mL, 11.7mmol) was added by injection, and acryloyl chloride (0.95mL, 11.7mmol) was slowly added dropwise in 2mL of anhydrous CH 2 Cl 2 Solution, a large amount of white smoke will be generated when dripping, after dripping, use 3ml of anhydrous CH 2 Cl 2 Rinse the buret. React at room temperature for 2 h, TLC showed that the raw materials basically disappeared, add 10 mL of saturated saline, stir for half an hour, CH 2 Cl 2 Extracted four times, the organic phase with anhydrous MgSO 4 dry. The desiccant was filtered, and the solvent was evaporated under reduced pressure to obtain a yellow viscous oil (3), which was drained and set aside.

Embodiment 3

[0033] Example 3: Synthesis of 7-hydroxyl-2,3-dihydroindan-1-one (4)

[0034]Add compound 3 and 11 g of anhydrous AlCl in a balloon-protected closed system 3 , the oil bath was heated to 150-160°C, and the reactant smoked violently. After reacting for 6 hours, cool to room temperature, and slowly add 2M hydrochloric acid dropwise to quench the reaction under cooling in an ice-water bath. During this process, the exothermic heat is violent until the solid basically dissolves and turns into a black solution. Ethyl acetate was extracted four times until TLC of the extract showed no product point. Combined organic phases, anhydrous MgSO 4 dry. TLC showed raw material (R f =0.83, developer: petroleum ether / ethyl acetate=10:1) has all disappeared, and there are two new spots (R f = 0.41 and R f = 0.22) generated. The desiccant was filtered, the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography separation, eluent: ...

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Abstract

The invention discloses a di(7-hydroxy-2,3-dihydro-1H-inden-1-yl) ether and analogue, synthesizing method and application in the pharmacy, which is characterized by the following: the structure of the ether possesses formula I and formula II, which improves anti-HCV activity and better anti-HIV activity; the product can be used to study and develop new drug with obvious scientific meaning and using prospect.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to di(7-hydroxy-2,3-dihydro-1-1H-indenyl) ethers (English name: di(7-hydroxy-2,3-dihydro-1H-inden -1-yl)ether) and its analogs, synthesis methods and pharmaceutical applications. Background technique [0002] In the 1970s, Hepatitis C Virus (HCV) was clinically discovered, and in the 1980s it was confirmed by molecular cloning techniques. HCV is the pathogen of hepatitis C and the main pathogenic factor leading to post-transfusion hepatitis and acute and chronic non-A non-B hepatitis. According to relevant statistics, about 55% to 85% of HCV acute infection develops into chronic infection, and chronic infection is the main cause of chronic hepatitis, liver cirrhosis and liver cancer death. In the United States, HCV infection is the disease that most commonly leads to liver transplantation. HCV can be transmitted through contaminated blood products, shared injection equipment for int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/196C07C41/09C07C41/00A61K31/075A61P31/12A61P1/16A61P31/18
Inventor 夏鹏王洋
Owner FUDAN UNIV
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