Capsaicin-containing nicotinic acid derivative, preparation method and use thereof

A technology of nicotinic acid esters and compounds, which is applied in the field of capsaicin-containing nicotinic acid capsaicin ester derivatives, preparation and use, can solve the problems of insufficient capsaicin activity, poor water solubility of capsaicin, difficulty in absorbing irritants, etc., and facilitate industrialization Production, appetite-stimulating, and digestion-improving effects

A technology of nicotinic acid esters and compounds, which is applied in the field of capsaicin-containing nicotinic acid capsaicin ester derivatives, preparation and use, can solve the problems of insufficient capsaicin activity, poor water solubility of capsaicin, difficulty in absorbing irritants, etc., and facilitate industrialization Production, appetite-stimulating, and digestion-improving effects

CN108069898BActive Publication Date: 2021-11-23NANHUA UNIV
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  • Capsaicin-containing nicotinic acid derivative, preparation method and use thereof
  • Capsaicin-containing nicotinic acid derivative, preparation method and use thereof
  • Capsaicin-containing nicotinic acid derivative, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] 8-methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (compound 1, code 1) and 8-methyl- Preparation of N-[(4-hydroxy-3-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (compound 2, code 2):

[0083]0.1mol 8-methyl-N-[(3,4-dihydroxyphenyl)-methyl]-(trans)-6-nonenylamide was mixed with 0.15mol in 100ml of thionyl chloride at 80°C Nicotinic acid was reacted for 10 hours, poured into an ice-water bath, extracted 3 times with ethyl acetate, dried over anhydrous sodium sulfate, and then column chromatographed with ethyl acetate:petroleum ether=1:2~1:5 to obtain the target product 8 -Methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide, yield 48.8%; and 8-methyl-N-[ (4-Hydroxy-3-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide, yield 44.3%. The relevant data are as follows:

[0084] 8-Methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (Compound 1) MS(EI,70ev)m / z: 370; Anal. Calcd. for C21H26O4N2: C, 68.21, H...

Embodiment 2

[0088] Preparation of 8-methyl-N-[(3-methoxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (Compound 3):

[0089] Dissolve 0.2mol of methyl iodide and 0.1mol of 8-methyl-N-[(3-methoxy-4-hydroxyphenyl)-methyl]-(trans)-6-nonenylamide in 300ml of acetone , add 12 grams of catalyst K2CO3, and react with 0.15mol nicotinic acid at 80°C for 3 hours to obtain the target product 8-methyl-N-[(3-methoxy-4-nicotinate phenyl)-methyl]- (trans)-6-Nonenylamide. The relevant data are as follows:

[0090] MS (EI, 70ev) m / z: 384; Anal. Calcd. for C22H28O4N2: C, 68.75, H, 7.29, N 7.29; Found C, 68.70, H, 7.25, N 7.24.

Embodiment 3

[0092] Preparation of 8-methyl-N-[(4-methoxy-3-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (Compound 4)

[0093] According to the operation of Example 2, just use 8-methyl-N-[(4-methoxy-3-hydroxyphenyl)-methyl]-(trans)-6-nonenylamide instead of 8-methyl -N-[(3-methoxy-4-hydroxyphenyl)-methyl]-(trans)-6-nonenylamide to give the compound 8-methyl-N-[(4-methoxy- 3-Nicotinate phenyl)-methyl]-(trans)-6-nonenylamide. The relevant data are as follows:

[0094] MS (EI, 70ev) m / z: 384; Anal. Calcd. for C22H28O4N2: C, 68.75, H, 7.29, N 7.29; Found C, 68.70, H, 7.25, N 7.24.

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Abstract

The present invention provides a class of nicotinic acid-containing capsaicin derivatives with general structural formula I and a production method thereof, and such derivatives have analgesic, anti-tumor, anti-inflammatory, anti-atherosclerosis, lowering blood fat, promoting Appetite, improving digestion, antibacterial and insecticidal, antioxidative, antiviral purposes.

Description

technical field [0001] The invention relates to a class of capsaicin-containing nicotinic acid derivatives and a manufacturing method thereof, and such derivatives have the functions of analgesia, anti-tumor, anti-inflammation, anti-atherosclerosis, lowering blood fat, promoting appetite, improving digestion, antibacterial and antibacterial properties. Insect, anti-oxidant, anti-viral purposes. 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...

Claims

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Application Information

Patent Timeline
23 Nov 2021
Publication
CN108069898B
IPC
C07D213/80; C07D213/803; A61K31/455; A61P29/00; A61P35/00; A61P9/10; A61P3/06; A61P1/14; A61P31/00; A61P31/12
CPC
C07D213/80; C07D213/803
Inventors
郑兴; 姚旭