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Preparation method for couplet benzene ring octadiene system lignans and application thereof

A technology of biphenyl cyclooctadiene and lignans, which is applied in the fields of heterocyclic compound active ingredients, antiviral agents, organic chemistry, etc., and can solve the synthesis method of biphenyl cyclooctadiene lignin compounds that have not been seen reports and other issues

Inactive Publication Date: 2008-12-10
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, there is no report on the synthesis method of biphenyl cyclooctadiene lignin compounds in the prior art

Method used

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  • Preparation method for couplet benzene ring octadiene system lignans and application thereof
  • Preparation method for couplet benzene ring octadiene system lignans and application thereof
  • Preparation method for couplet benzene ring octadiene system lignans and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090]

[0091] Dissolve 0.1 mol of gallic acid in 250 mL of freshly distilled methanol, slowly add 0.01 mol of concentrated sulfuric acid dropwise, and reflux for 17 hours. After the completion of the reaction detected by TLC, part of the solvent was evaporated under reduced pressure, and poured into 500 mL of saturated potassium carbonate aqueous solution, a white solid was precipitated. A white solid was separated and the aqueous phase was extracted with ethyl acetate (3 x 200 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated, and the obtained white solid was compound 1 after drying.

[0092] The yield of this reaction process was 97%. The relevant test data is as follows:

[0093] 1 H-NMR (300MHz, CDCl 3 ): δ=6.82(2H), 3.87(3H).

Embodiment 2

[0095]

[0096] Equipped with a Dean-Stark apparatus, take 150 mmol of the compound obtained in Example 1 and dissolve it in 200 mL of benzene, add 150 mmol of triethyl orthoformate and 5 mg / mmol of acidic resin Amberlyst 15E, reflux, filter after TLC detection and trace the disappearance of raw materials, and concentrate the filtrate Compound 2 was obtained by column chromatography.

[0097] The yield of this reaction process was 98%. The relevant test data is as follows:

[0098] 1 H-NMR (300MHz, CDCl 3 ): δ=7.39(1H), 7.28(1H), 7.06(1H), 3.87(3H), 3.56(2H), 1.2(3H).

Embodiment 3

[0100]

[0101] Dissolve 240mmol of the compound obtained in Example 2 in 200mL of acetone, add 60mmol of methyl iodide or benzyl bromide, and 60mmol of potassium carbonate, reflux reaction, TLC detection after the reaction is complete, filter, concentrate, and column chromatography to obtain compound 3 or compound 4.

[0102] The yield of this reaction process was 96%. The relevant test data is as follows:

[0103] Compound 3 1 H-NMR (300MHz, CDCl 3 ): δ=7.28(1H), 7.25(1H), 7.10(1H), 3.89(3H), 3.86(3H), 3.62(2H), 1.34(3H).

[0104] Compound 4 1 H-NMR (300MHz, CDCl 3 ): δ=7.21-7.41(8H), 5.06(2H), 3.87(3H), 3.81(2H), 1.23(3H).

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Abstract

The invention provides a method for preparing dibenzocyclooctadiene lignan as shown in formula (I) and an application of the dibenzocyclooctadiene lignan on anti-HIV-1. The method has readily available raw materials, and simple and easy operation, and the prepared compound has remarkable anti-HIV-1 activity. R1=OH, R2=OCH3 or R1=OCH3.

Description

technical field [0001] The present invention relates to the preparation method of the compound biphenyl cyclooctadiene lignans represented by the structural formula (I), and its application in the preparation of anti-AIDS (HIV-1) medicine. [0002] [0003] R 1 =OH,R 2 =OCH 3 or R 1 =OCH 3 , R 2 =OH Background technique [0004] Since the first case of AIDS was reported in 1981, its epidemic has spread rapidly to countries all over the world. According to the report of the Ministry of Health: As of October 31, 2006, there have been 183,733 AIDS cases reported nationwide, including 40,667 AIDS patients and 12,464 deaths. The epidemic situation is relatively serious, and the possibility of further spread still exists. In February 2006, the State Council promulgated the "National Medium- and Long-Term Science and Technology Development Program Outline", which has included "Prevention and Treatment of Major Infectious Diseases such as AIDS and Viral Hepatitis" as one o...

Claims

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Application Information

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IPC IPC(8): C07D317/70A61K31/36A61P31/18
Inventor 刘靖平孙汉董张洪彬肖伟烈李蓉涛普建新
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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