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Curcumenol derivative, preparation method and application of curcumenol derivative in preparation of anti-inflammatory drugs

A technology of curcumol and its derivatives, which is applied in the preparation of heterocyclic compounds, anti-inflammatory agents, drug combinations, etc., can solve the problems of aggravating infection and achieve the effect of reducing the level of inflammatory cytokines

Active Publication Date: 2022-04-12
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, anti-inflammatory drugs are the second largest class of drugs after anti-infective drugs in clinical treatment. Clinically used anti-inflammatory drugs mainly include non-steroidal anti-inflammatory drugs and steroidal anti-inflammatory drugs, but they all have different Degree of adverse reactions, such as non-steroidal anti-inflammatory drugs to stimulate the gastrointestinal tract and kidney damage, glucocorticoids may induce or aggravate infection, etc.

Method used

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  • Curcumenol derivative, preparation method and application of curcumenol derivative in preparation of anti-inflammatory drugs
  • Curcumenol derivative, preparation method and application of curcumenol derivative in preparation of anti-inflammatory drugs
  • Curcumenol derivative, preparation method and application of curcumenol derivative in preparation of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of Curcumol Monoester Derivatives

[0037] Curcumol (3g, 1equiv.) was dissolved in dichloromethane, m-chloroperoxybenzoic acid (3.28g, 1.5equiv.) was added, stirred at room temperature, TLC (5% sulfuric acid ethanol for color development) tracked until the reaction was complete , washed successively with saturated sodium bisulfite, saturated sodium bicarbonate, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain an oily liquid, and its oily liquid was dissolved in isopropanol, and sodium hydroxide (1.525 g, 3equiv.), reacted at 70°C, followed by TLC (5% sulfuric acid ethanol for color development) until the reaction was complete, washed with saturated tartaric acid and saturated brine successively, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and passed through column chromatography (petroleum oil) Ether:ethyl acetate=3:1) to isolate 2.242g white solid intermediate (IM), yield...

Embodiment 2

[0041] Synthesis of Curcumol Diester Derivatives

[0042] Synthetic intermediate IM, synthetic method is the same as embodiment 1.

[0043]Dissolve the intermediate IM (50 mg, 1 equiv.) in N, N-dimethylformamide (DMF), add sodium hydride (48 mg, 10 equiv.) and a catalytic amount of potassium iodide in sequence, stir at room temperature for 15 min, and then add p-nitrobenzene Formyl chloride (110 mg, 3 equiv.), stirred at room temperature, followed by TLC (5% sulfuric acid ethanol for color development) until the reaction was complete, quenched with water, washed with saturated tartaric acid and saturated brine successively, dried over anhydrous sodium sulfate, and concentrated under reduced pressure , separated by column chromatography (petroleum ether: ethyl acetate = 15: 1) to obtain 43 mg of white solid, which is the curcumol diester derivative (2), with a yield of 40%.

[0044] 1 H NMR (600MHz, Acetone-d 6 )δ: 8.39 (t, J=8.9Hz, 4H, H-4′, H-6′ and H-4″, H-6″), 8.34–8.29 ...

Embodiment 3

[0046] Synthesis of Chlorine Substituted Derivatives of Curcumol Monoalcohol

[0047] Synthetic intermediate IM, synthetic method is the same as embodiment 1.

[0048] The intermediate IM (50 mg, 1 equiv.) was dissolved in dichloromethane, and N-chlorosuccinimide (NCS) (40 mg, 1.5 equiv.) and triphenylphosphine (PPh3) (78 mg, 1.5 equiv.), stirring at room temperature, followed by TLC (5% sulfuric acid ethanol color) until the reaction was complete, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=15: 1) 43 mg of a colorless transparent liquid was isolated, namely curcumol monoalcohol chlorine-substituted derivative (3), with a yield of 81%.

[0049] 1 H NMR (600MHz, CDCl 3 )δ:5.92(s,1H,H-7),4.01(s,2H,H-9),1.03(d,J=6.7Hz,3H,H-11),1.00(d,J=6.5Hz, 3H,H-12),0.89(d,J=6.6Hz,3H,H-13); 13 C NMR (150MHz, CDCl 3 )δ: 140.06(C-8), 128.75(C-7), 103.27(C-6), 87.44(C-3α), 59....

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Abstract

The invention relates to the technical field of medicines, and discloses curcumenol derivatives, a preparation method and application of the curcumenol derivatives in preparation of anti-inflammatory medicines. The curcumenol derivative is designed and synthesized by taking curcumenol as a precursor. The curcumenol derivative has no influence on growth of mouse primary peritoneal macrophages, can significantly reduce the inflammatory cytokine level, has anti-inflammatory activity, and provides a new choice for research and development of anti-inflammatory drugs.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to curcumol derivatives, a preparation method and their application in the preparation of anti-inflammatory drugs. Background technique [0002] Inflammation is a pathophysiological process in which living tissues with a vascular system are stimulated by various damage factors and is mainly a defense response. It is involved in many diseases (such as cardiovascular disease, osteoporosis, diabetes, autoimmune disease, atherosclerosis, neurodegenerative diseases, etc.). At present, anti-inflammatory drugs are the second largest class of drugs after anti-infective drugs in clinical treatment. Clinically used anti-inflammatory drugs mainly include non-steroidal anti-inflammatory drugs and steroidal anti-inflammatory drugs, but they all have different The degree of adverse reactions, such as non-steroidal anti-inflammatory drugs to stimulate the gastrointestinal tract and kidney damag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C07C49/637C07C45/60A61P29/00A61K31/35A61K31/122
CPCY02A50/30
Inventor 黄烈军周红郝小江罗静陈亮黄雅思金军高福田蹇军友顾玮苑春茂石京山
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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