Nitro-containing curcumin derivative as well as preparation method and application thereof

A technology of curcumin derivatives and nitro groups, which is applied in the field of nitro-containing curcumin derivatives and their preparation, can solve the problems of low bioavailability, instability, poor water solubility, etc., and achieve low preparation cost and high structure Stable and achievable effect

Active Publication Date: 2015-04-29
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Curcumin is soluble in methanol, ethanol, propylene glycol, and slightly soluble in water. It has the advantages of broad anti-cancer spectrum and small toxic and side effects. However, because of its poor water solubility, it is unstable under neutral and alkaline conditions, and its bioavailability is low. Disadvantages seriously affect its clinical application

Method used

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  • Nitro-containing curcumin derivative as well as preparation method and application thereof
  • Nitro-containing curcumin derivative as well as preparation method and application thereof
  • Nitro-containing curcumin derivative as well as preparation method and application thereof

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preparation example Construction

[0053] The invention provides a kind of preparation method of the curcumin derivative containing nitro, comprise making the substituent of the benzaldehyde with general formula (II) and formula (III) (E)-2-(2-nitrobenzylidene ) cyclohexanone undergoes aldol condensation reaction,

[0054]

[0055] Wherein R represents one or more substituents connected to the benzene ring, selected from H, halogen atoms, OH and optional lower alkoxy groups.

[0056] The preparation method of described nitro-containing curcumin derivatives specifically comprises the steps of: combining benzaldehyde substituents shown in formula (II) with formula (III) (E)-2-(2-nitrobenzylidene ) cyclohexanone is dissolved in the organic solvent a, catalyst b is added, and the reaction is complete at room temperature to obtain the reaction solution c, after the reaction solution c is post-treated and separated and purified, the curcumin derivative shown in the formula (I) is obtained; Described organic solve...

Embodiment 1

[0069] Preparation of (E)-2-(2-nitrobenzylidene)cyclohexanone

[0070] Cyclohexanone (9.8g, 0.1mol), morpholine (10.45g, 0.12mol) and p-toluenesulfonic acid (0.04g, 0.23mmol) were dissolved in 30mL of toluene, heated to reflux for 6h. After the reaction was cooled to room temperature, the toluene was evaporated off. Then, 4-(cyclohexanon-1-yl)morpholine (4.61g, 0.027mol) and o-nitrobenzaldehyde (4.0g, 0.023mol) were dissolved in 20mL of ethanol and reacted at 90°C for 6h. After the reaction was monitored by TLC, the pH was adjusted to 3 with 5% dilute hydrochloric acid. After the ethanol was evaporated by rotary evaporation, ethyl acetate was added for extraction, the organic layer was washed with water, washed with salt, and anhydrous MgSO 4 Dry, filter, and spin-dry the organic layer to obtain a crude product, and perform column purification to obtain a light yellow pure product with a yield of 51.7%.

Embodiment 2

[0072] Preparation of (2E, 6E)-2-(3,4-dimethoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (a9)

[0073] (E)-2-(2-nitrobenzylidene)cyclohexanone (100mg, 0.43mmol), 3,4-dimethoxybenzaldehyde (71.86mg, 0.43mmol) was dissolved in 6mL of absolute ethanol, Add 6 drops of 20% sodium hydroxide solution dropwise, react at room temperature for 24 hours, a yellow precipitate precipitates out of the solution, filter, wash with water and dilute ethanol until pure by TLC, and the yield is 70.6%.

[0074] Yellow powder, 70.6% yield, mp 131.8-135.5℃. 1 H NMR (600MHz, CDCl 3 ): δ (ppm) 8.225 (1H, d, J=7.2Hz, H-3), 7.947 (1H, s, H-β), 7.792 (1H, s, H-β'), 7.640 (1H, t , J=7.5Hz, H-4), 7.500(1H, t, J=7.8Hz, H-5), 7.370(1H, d, J=7.8Hz, H-6), 7.123(1H, d, J =8, 4Hz, H-6'), 7.027 (1H, s, H-2'), 6.915 (1H, d, J=8.4Hz, H-5'), 3.928 (3H, s, 3'-OCH 3 ), 3.914 (3H, s, 4'-OCH 3 ), 2.949 (2H, t, J=5.1Hz, Cyclohexanone-C H 2 CH 2 CH 2 -), 2.605 (2H, t, J=5.1Hz, Cyclohexanone-CH 2 CH 2 C H...

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Abstract

The invention discloses a curcumin derivative as shown in formula (I) as well as a preparation method and application of the curcumin derivative. The invention provides a novel curcumin derivative, and the derivative has an anti-inflammatory activity and can be used as an active ingredient in anti-inflammatory drugs or anti-inflammatory pharmaceutical compositions. Furthermore, the invention also provides a preparation method of the curcumin derivative as shown in formula (I). The invention belongs to the technical field of chemical drugs; the curcumin derivative is better than curcumin in stability, and the curcumin derivative is low in preparation cost and good in realizability.

Description

technical field [0001] The invention belongs to the technical field of chemical medicines, and in particular relates to a nitro-containing curcumin derivative and a preparation method and application thereof. Background technique [0002] Curcumin is a plant polyphenol derived from the rhizomes of turmeric, turmeric, curcuma, calamus, etc. It has anti-oxidation, anti-infection, anti-inflammation, lowering blood lipids, anti-atherosclerosis and inhibiting tumor growth. Curcumin is soluble in methanol, ethanol, propylene glycol, and slightly soluble in water. It has the advantages of broad anti-cancer spectrum and small toxic and side effects. However, because of its poor water solubility, it is unstable under neutral and alkaline conditions, and its bioavailability is low. The disadvantages seriously affect its clinical application. [0003] In recent years, studies have found that nitro-containing curcumin derivatives have anti-inflammatory activity. At the same time, expe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/45A61K31/122A61P29/00
Inventor 梁广张亚利刘志国冯建鹏陈文波俞鹏天
Owner WENZHOU MEDICAL UNIV
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