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Salicylic acid-containing capsaicin ester derivative, preparation method and application

A hydrate and compound technology, applied in the field of capsaicin salicylate derivatives and their preparation, can solve the problems of low bioavailability, limited application, difficult to absorb irritation and the like

Active Publication Date: 2018-05-25
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Capsaicin has a good analgesic effect, but due to the poor water solubility of capsaicin, it is difficult to absorb and irritating when taken orally, which limits its application
In addition, further studies have found that the activity of capsaicin in the body is not high enough, the absorption is small, the metabolism is fast, and the bioavailability is low, which further limits its application.

Method used

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  • Salicylic acid-containing capsaicin ester derivative, preparation method and application
  • Salicylic acid-containing capsaicin ester derivative, preparation method and application
  • Salicylic acid-containing capsaicin ester derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of (E)-8-methyl-N-(4-salicyloyloxy-3-methoxybenzyl)-6-nonenamide (compound 1, code 01)

[0063]

[0064] React 0.01mol salicylic acid with 3ml of thionyl chloride at 70°C, add 2 drops of catalyst pyridine, and react for 2 hours to remove excess thionyl chloride by suction filtration under reduced pressure, dissolve in 10ml of dichloromethane, and place on ice Stir in the bath. Dissolve 0.01mol capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide) and pyridine in dichloromethane, add dropwise to the reaction flask through a constant pressure funnel (0.5h), and drop Stir at 25°C for 7 hours. The target product was obtained by column chromatography with ethyl acetate:petroleum ether=1:3. The relevant data are as follows:

[0065] Code 01EI-MS m / z:425.2; Anal.Calcd.For C 25 h 31 NO 5 : C,70.57; H,7.34; N,3.29; Found C,70.57; H,7.32; N,3.28

Embodiment 2

[0067] Preparation of 8-methyl-N-(4-salicyloyloxy-3-methoxybenzyl)nonanamide (compound 2, code 02)

[0068]

[0069] React 0.01mol salicylic acid with 3ml of dichloromethane containing phosphorus pentachloride at 50°C, add 2 drops of catalyst pyridine, react for 5 hours and remove excess thionyl chloride by suction filtration under reduced pressure, and use 10ml of dichloromethane Dissolve and stir in an ice bath. Dissolve 0.01mol dihydrocapsaicin (N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide) and pyridine in dichloromethane, and add it dropwise to the reaction flask through a constant pressure funnel (1h), and stirred at 35° C. for 10 hours after dropping. The target product was obtained by column chromatography with ethyl acetate:petroleum ether=1:3. The relevant data are as follows:

[0070] Code 02EI-MS m / z:427.2; Anal.Calcd.For C 25 h 33 NO 5 : C,70.23; H,7.78; N,3.28; Found C,70.25; H,7.75; N,3.26

Embodiment 3

[0072] Preparation of 7-methyl-N-(4-salicyloyloxy-3-methoxybenzyl) octanamide (compound 3, code 03)

[0073]

[0074] React 0.01mol salicylic acid with 3ml of thionyl chloride at 80°C, add 2 drops of catalyst triethylamine, and react for 1 hour to remove excess thionyl chloride by suction filtration under reduced pressure, dissolve in 10ml of acetone, and place on ice Stir in the bath. Dissolve 0.01mol nordihydrocapsaicin (7-Methyl-N-vanillyl-octamide) and triethylamine in acetone, add dropwise into the reaction flask through a constant pressure funnel (0.5h), and stir at 10°C for 5 Hour. The target product was obtained by column chromatography with ethyl acetate:petroleum ether=1:3. The relevant data are as follows:

[0075] Code 03EI-MS m / z:413.2; Anal.Calcd.For C 24 h 31 NO 5 : C,69.71; H,7.56; N,3.39; Found C,69.69; H,7.54; N,3.37

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PUM

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Abstract

The invention provides a salicylic acid-containing capsaicin ester derivative with a general structural formula I and a preparation method thereof. The derivative has anti-inflammatory, analgesic, anti-cancer, antibacterial and hypolipidemic aspect applications.

Description

technical field [0001] The invention relates to a class of capsaicin derivatives containing salicylic acid and a preparation method thereof, and the uses of the derivatives in anti-inflammation, labor pain, anti-cancer, anti-bacteria and blood fat reduction. Background technique [0002] Capsaicin is a main active ingredient in the spicy ingredients of capsicum fruit. At present, this kind of substance has been widely used as an additive in the chemical industry and in the pharmaceutical industry. Capsaicin has various pharmacological activities such as analgesia, anti-tumor, anti-inflammation, anti-atherosclerosis, lowering blood lipid, promoting appetite, improving digestion, antibacterial and insecticidal, anti-oxidation, anti-viral and selective for neurotransmitters and pharmacological effects. Capsaicin has a good analgesic effect, but due to the poor water solubility of capsaicin, it is difficult to absorb and irritating when taken orally, which limits its applicatio...

Claims

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Application Information

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IPC IPC(8): C07C233/20C07C233/18C07C231/12A61K31/618A61K31/621A61P29/00A61P35/00A61P31/00A61P3/06A61P3/10A61P9/12
CPCC07C233/18C07C233/20
Inventor 郑兴杨泽华刘倬姚旭陈洪飞龙进向梦辉李红
Owner NANHUA UNIV
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