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Derivatives containing capsaicin salicylate, preparation method and use

A compound, C1-C6 technology, applied in the field of capsaicin-containing salicylate derivatives and its preparation, can solve the problems of low bioavailability, low absorption, and insufficient capsaicin activity

Active Publication Date: 2021-04-16
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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  • Derivatives containing capsaicin salicylate, preparation method and use
  • Derivatives containing capsaicin salicylate, preparation method and use
  • Derivatives containing capsaicin salicylate, preparation method and use

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, and add it dropwise into the reaction flask through a constant pressure funnel (0.5h). 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 to 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 class of capsaicin-containing salicylate derivatives with general structural formula I and a preparation method thereof, and the derivatives have the uses of anti-inflammation, labor pain, anti-cancer, antibacterial and hypolipidemic.

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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Patent Type & Authority Patents(China)
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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