Nicotinic acid-contained curcumin ester derivative and preparation method and application thereof

A technology of nicotinic acid curcumin ester and acid curcumin ester, applied in the field of nicotinic acid curcumin ester derivatives and their manufacture, can solve problems such as failure to effectively solve problems, achieve convenient industrial production, excellent blood lipid lowering, less toxic effect

Inactive Publication Date: 2010-08-18
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the technology of above-mentioned patent, bibliographical report all fails to solve the problem effectively

Method used

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  • Nicotinic acid-contained curcumin ester derivative and preparation method and application thereof
  • Nicotinic acid-contained curcumin ester derivative and preparation method and application thereof
  • Nicotinic acid-contained curcumin ester derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 4′-Hydroxy-4″-nicotinic acid curcuminate (code 101), 4″-hydroxy-4′-nicotinic acid curcuminate (code 109) and 4′,4″-nicotinic acid curcuminate (code 109) 118) Preparation:

[0056] React 0.01mol curcumin in 10ml thionyl chloride with 0.03mol nicotinic acid at 75°C for 10 hours, pour into an ice-water bath, extract 3 times with ethyl acetate, dry over anhydrous sodium sulfate, and then use ethyl acetate : Petroleum ether=1: 3 column chromatography, obtain target product 4 '-hydroxyl-4 "-nicotinic acid curcuminate (code number 101), 4 "-hydroxyl-4'-nicotinic acid curcuminate (code number 109) and 4′, 4″-curcumin dinicotinate (code 118). Relevant data are as follows:

[0057] 4′-Hydroxy-4″-nicotinic acid curcuminate (code 101): MS (EI, 70ev) m / z: 473; Anal.Calcd.for C 27 h 23 NO 7 : C, 68.49, H, 4.90, N 2.96; Found C, 68.22, H, 4.80, N 2.95.

[0058] 4″-Hydroxy-4′-nicotinic acid curcuminate (code 109): MS (EI, 70ev) m / z: 473; Anal.Calcd.for C 27 h 23 NO 7 : C, 68.49...

Embodiment 2

[0061] The preparation of 4'-methoxy-4 "-nicotinic acid curcuminate (code name 102):

[0062] Dissolve 0.03mol methyl iodide and 0.01mol 4′-hydroxy-4″-nicotinic acid curcuminate (code 101) in 25ml acetone, add 10 grams of catalyst K 2 CO 3 , reacted at 60°C for 4 hours to obtain the target product 4'-methoxy-4"-nicotinic acid curcuminate. The relevant data are as follows:

[0063] MS (EI, 70ev) m / z: 487; Anal. Calcd. for C 28 h 25 NO 7 : C, 68.98, H, 5.17, N 2.87; Found C, 68.93, H, 5.19, N 2.86.

Embodiment 3

[0065] 4'-Ethoxy-4"-nicotinic acid curcuminate (code 103), 4'-propoxy-4"-nicotinic acid curcuminate (code 104), 4'-benzyloxy-4"- Nicotinic acid curcuminate (code 105), 4'-heptyloxy-4"-nicotinic acid curcuminate (code 106), 4'-octyloxy-4"-nicotinic acid curcuminate (code 107), Preparation of 4'-decyloxy-4"-nicotinic acid curcuminate (code number 108):

[0066] Replace methyl iodide with 0.03mol haloalkane according to the operation of Example 2 to obtain compound 4'-ethoxy-4"-nicotinic acid curcuminate (code number 103), 4'-propoxyl-4"-nicotinic acid curcumin Ester (code 104), 4'-benzyloxy-4"-nicotinic acid curcuminate (code 105), 4'-heptyloxy-4"-nicotinic acid curcuminate (code 106), 4'-octyl Oxy-4″-nicotinic acid curcuminate (code 107), 4′-decyloxy-4″-nicotinic acid curcuminate (code 108). The relevant data are as follows:

[0067] 4′-Ethoxy-4″-nicotinic acid curcuminate (code 103): MS (EI, 70ev) m / z: 501; Anal.Calcd.for C 29 h 27 NO 7 : C, 69.45, H, 5.43, N 2.79; Found...

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Abstract

The invention relates to a nicotinic acid-contained curcumin ester derivative and a preparation method and application thereof. The curcumin has various physiological activities and pharmacological effects, such as the resistance of inflammation, bacterium, tumor, tracheitis and oxidation, blood pressure reduction, neuroprotection, and the like. The compound and salts thereof can be used for preparing medicaments of resisting inflammation, cancers, bacteria and viruses, lowering blood pressure and blood sugar and adjusting blood fat. The compound has the excellent effects of lowering blood fat, blood sugar and blood pressure and resisting cancers, bacteria and viruses, has less toxicity, easy preparation method, convenient industrial production, can satisfy the need of the medical field and has the advantages of high curative effect, low toxicity, and the like.

Description

technical field [0001] The invention relates to a medicine, in particular to a niacin-containing curcumin ester derivative with anti-inflammatory, blood-lipid-regulating, blood-sugar-lowering, anti-cancer, anti-hypertensive, anti-bacterial and anti-viral functions and its production method and application. Background technique [0002] Curcumin is an important active ingredient found in almost all ginger plants. Curcumin has various physiological activities and pharmacological effects such as anti-inflammatory, antibacterial, anti-tumor, lowering blood pressure, preventing and treating bronchitis, anti-oxidation and neuroprotection. Curcumin has entered Phase I clinical trials in the United States. However, further studies have found that curcumin has low activity in the body, low absorption in the body, fast metabolism and low bioavailability, these characteristics greatly limit its application. Currently, the structural modification of curcumin mainly focuses on the foll...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/80C07D213/803A61K31/44A61K31/444A61P29/00A61P3/06A61P3/10A61P9/12A61P35/00A61P31/00A61P31/12A61P25/00
Inventor 廖端芳郑兴庹勤慧朱炳阳
Owner NANHUA UNIV
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