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Derivative of natural product selaginpulvilin as well as preparation method and application of derivative

A technology of natural products and derivatives, applied in the field of medicine and chemical industry, to achieve significant inhibitory effects and good application prospects

Active Publication Date: 2017-05-31
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, taking such drugs can cause adverse reactions such as diarrhea and nausea. Therefore, how to overcome the adverse reactions of these PDE4 inhibitors and study new specific inhibitors has become one of the research hotspots.

Method used

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  • Derivative of natural product selaginpulvilin as well as preparation method and application of derivative
  • Derivative of natural product selaginpulvilin as well as preparation method and application of derivative
  • Derivative of natural product selaginpulvilin as well as preparation method and application of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 2-Bromo-3-methylbenzoic acid (21.3mmol), palladium acetate (0.24g, 1.06mmol), iodobenzene diacetate (6.86g, 21.3mmol) and iodine (5.42g, 21.3mmol) in 250mL round bottom In the flask. Add DMF (50mL) to dissolve and react at 100°C for 24-36h. After cooling to room temperature, 500 mL ethyl acetate was added, and DMF was removed by washing with 0.5N hydrochloric acid three times. The organic layer was concentrated under reduced pressure and purified by column (petroleum ether / dichloromethane) to obtain compound 2.

Embodiment 2

[0050] Compound 2 (20.0 mmol) was dissolved in acetone (50.0 mL), and K was added successively at room temperature 2 CO 3 (5.52g, 40.0mmol) and MeI (1.9mL, 30.0mmol), reflux for 3h. After the reaction was completed, it was quenched by adding water, and extracted three times with ethyl acetate. The organic layers were combined and concentrated under reduced pressure to obtain the esterified product.

[0051] The above-mentioned esterification product (15.4mmol), 4-methoxyphenylboronic acid (2.34g, 15.4mmol), Pd(PPh 3 ) 4 (0.89g, 0.77mmo), and K 2 CO 3 (6.37g, 46.1mmol) in a double-necked flask, add DMF (50mL) and H under nitrogen protection 2 O (8mL). Stir overnight at 100°C, cool to room temperature, add saturated aqueous ammonium chloride solution, and extract three times with ethyl acetate. The organic layers were combined, concentrated under reduced pressure, and purified by column (petroleum ether / dichloromethane) to obtain compound 3.

Embodiment 3

[0053] Dissolve compound 3 (13.3mmol) in MeSO 3 H (10 mL). After stirring at 65°C overnight, the reaction was quenched by adding water (200 mL), and extracted three times with ethyl acetate. The organic layers were combined and concentrated under reduced pressure to obtain compound 4.

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PUM

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Abstract

The invention belongs to the technical field of drugs and chemicals and discloses a derivative of a natural product selaginpulvilin. The invention further provides a preparation method of the derivative and application of the derivative for preparing anti-inflammatory drugs. The structure of the derivative of the natural product selaginpulvilin disclosed by the invention is shown as a formula (I) or a formula (II), wherein R1 is alkyl, aldehyde, carboxyl, alcohol group, hydroxyl, acyl or hydrogen; R2 is hydrogen or hydroxyl; R3 is alkoxy, acyl or hydroxyl; R4 is halogen, aryl ethynyl, phenyl or substituted phenyl and aryl vinyl; R5 is hydrogen, hydroxyl, phenyl or substituted-phenyl;R6 is hydrogen, phenyl or substituted phenyl;the substituent group is selected from alkoxy, acyl or hydroxyl. The derivative of the natural product selaginpulvilin has an obvious effect of inhibiting phosphodiesterase IV, and has wide application space in preparation of the anti-inflammatory drugs. The structural formula is as shown in the specification.

Description

Technical field [0001] The present invention relates to the field of medicine and chemical industry, and more specifically, to a derivative of natural product selaginpulvilin and its preparation method and application. Background technique [0002] Cyclic nucleotide phosphodiesterases (PDEs) are an important family of super enzymes, which effectively control intracellular cAMP and cyclic adenosine monophosphate (Camp) and cGMP hydrolysis. The concentration of cyclic guanosine monophosphate (cGMP) can regulate the biochemical effects conducted by the second messenger in the body. PDEs are widely distributed in mammalian tissues, and their diversity results in a specific distribution of different PDE enzymes at the cellular and subcellular levels. They can selectively regulate a variety of cellular functions and are good targets for drug design and treatment. [0003] Phosphodiesterase IV (PDE4), as a PDE family enzyme that specifically catalyzes the hydrolysis of cAMP, is mainly di...

Claims

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Application Information

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IPC IPC(8): C07C39/23C07C47/57C07D311/94C07C65/19C07C43/315C07C43/215C07C69/21C07C43/23A61K31/05A61K31/11A61K31/366A61K31/192A61K31/075A61K31/09A61K31/222A61P29/00
CPCC07C39/23C07C43/215C07C43/23C07C43/315C07C47/57C07C65/19C07C69/21C07D311/94
Inventor 尹胜唐贵华张君生刘信
Owner SUN YAT SEN UNIV
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