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Curcumin derivative and uses thereof

A halogen and compound technology, applied in the field of medicinal chemistry, can solve problems such as short plasma half-life, poor stability of curcumin, and difficult oral absorption

Pending Publication Date: 2019-07-19
NANJING NORATECH MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to poor stability of curcumin, low solubility in water, short plasma half-life, low blood concentration, difficult oral absorption, low bioavailability in vivo, and large dosage limit the popularization and use of curcumin

Method used

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  • Curcumin derivative and uses thereof
  • Curcumin derivative and uses thereof
  • Curcumin derivative and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Preparation of Compound 1

[0053]

[0054] Preparation of intermediate 1-1 Boc-L-valine benzyl lactate

[0055] Under ice-bath conditions, 27.00g (150mmol) of benzyl lactate, 32.54g (150mmol) of Boc-valine, and 400mL of dichloromethane (DCM) were added to the three-necked reaction flask, and then 61.85g (300mmol) of DCC were added in batches Adding to the system, the adding speed is to control the system not to reflux. Then the temperature was naturally raised to room temperature, and the reaction was carried out until the benzyl lactate was completely converted. Stop the reaction, filter the reaction solution, spin the filtrate to dryness, then add 100mL diethyl ether to freeze in the refrigerator for more than 2 hours, then filter, dilute the filtrate with 400mL DCM, wash with ice-cold 200mL 1N sodium hydroxide, 200mL saturated saline, and then separate to obtain a DCM solution , dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-...

Embodiment 2

[0064] Example 2 Preparation of Compound 2

[0065]

[0066] Preparation of Intermediate 2-1 Acetyl Curcumin

[0067] Under ice-bath condition, curcumin 20.00g (54.28mmol), 21.46g pyridine (271.40mmol), 0.66gDMAP (5.40mmol) and 400mL DCM are added in the three-port reactor, then will contain acetic anhydride 5.54g (54.28mmol) DCM (40 mL) solution was added dropwise into the system, and the dropwise addition was completed in about 10 minutes. Then naturally warm up to room temperature and react for 2 hours. The reaction was stopped, and the reaction solution was washed with 200 mL of 1N hydrochloric acid and 200 mL of water, separated to obtain a DCM solution, dried over anhydrous sodium sulfate, and spin-dried to obtain a crude product. A yellow solid product (7.60 g, 34.1%) was obtained by silica gel column chromatography.

[0068] Preparation of intermediate 2-2 Boc-L-valine-lactic acid-acetyl curcumin

[0069] Acetyl curcumin 3.00g (7.30mmol), Boc-valyl lactic acid 2....

Embodiment 3

[0074] Example 3 Preparation of Compound 3

[0075]

[0076] Preparation of intermediate 3-1 curcumin monostearate

[0077] Under ice-bath condition, curcumin 10g (27.14mmol), 10.73g pyridine (135.70mmol), 0.33g DMAP (2.70mmol) and 200ml DCM are added in the three-necked reaction flask, then will contain stearic acid 5.81g (21.52mmol) 20mL of DCM solution was added dropwise into the system, and the dropwise addition was completed in about 10 minutes. Then naturally warm up to room temperature and react for 2 hours. The reaction was stopped, and the reaction solution was washed with 100 mL of 1N hydrochloric acid and 100 mL of water, separated to obtain a DCM solution, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to obtain a crude product, and silica gel was used to obtain a yellow solid product (4.20 g, 31.3%).

[0078] Intermediate 3-2 Preparation of Boc-L-valine-stearic acid-curcumin

[0079] Curcumin monostearate 3g (6.06mmol), Boc-vali...

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Abstract

The present invention relates to a curcumin derivative represented by a general formula (I) or a pharmaceutically acceptable salt thereof, and a preparation method thereof, a composition containing aneffective amount of the compound represented by the general formula (I) or the pharmaceutically acceptable salt thereof, and applications of the compound represented by the general formula (I) or thepharmaceutically acceptable salt thereof in preparation of drugs for treatment of cancers, fatty liver, inflammations and the like, wherein R<1> and R<2> are defined in the specification.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to curcumin derivatives with the general formula (I) or pharmaceutically acceptable salts thereof, and the application of such compounds in the preparation of drugs for treating cancer, fatty liver, inflammation and the like. Background technique [0002] Curcumin is one of the main active components of turmeric. It has a long history of medicinal use in Asia, especially India and China. It is also widely used in pigments, food additives and seasonings. Studies have shown that curcumin has pharmacological effects such as anti-tumor, anti-mutation, anti-proliferation, anti-inflammation, anti-oxidation, anti-human immunodeficiency virus, immune regulation, anti-fatty liver, liver and kidney protection, and anti-fibrosis. [0003] Anti-angiogenesis is one of the current molecular targeted therapy approaches. Studies have shown that curcumin can inhibit tumor angiogenesis and formati...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C69/28C07C271/54C07C271/48C07C271/52C07C271/44A61K31/27A61K31/23A61K31/223A61P35/00A61P29/00A61P31/18A61P1/16
CPCC07C229/08C07C69/28C07C271/54C07C271/48C07C271/52C07C271/44
Inventor 刘飞吴刚陈盼金龙宝孙吉叶
Owner NANJING NORATECH MEDICAL TECH CO LTD
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