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Antimicrobial and anti-tumor emodin compound and application thereof

A technology of compounds and derivatives, which is applied in the application fields of antitumor, antibacterial and anti-inflammatory drugs, and can solve the problems of high toxicity of emodin, insufficient biological activity, and unclear mechanism of biological activity, etc.

Inactive Publication Date: 2015-09-09
SHAOYANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Emodin is a tricyclic coplanar structure, which has the basic structural characteristics of a DNA intercalator (J Nat Prod, 2001, 64 (9): 1162-1168), but due to the high toxicity of emodin itself, the biological activity is not good enough and the biological activity The mechanism is not very clear and other shortcomings

Method used

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  • Antimicrobial and anti-tumor emodin compound and application thereof
  • Antimicrobial and anti-tumor emodin compound and application thereof
  • Antimicrobial and anti-tumor emodin compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment one: the synthesis of ethyl rhein

[0064]Add 0.22 g of rhein into the reaction flask, add 100 ml of dichloromethane, add 5 ml of thionyl chloride under stirring, and react overnight under reflux until the system is dissolved. Evaporate the solvent under reduced pressure to dryness, add 5 ml of toluene to remove the excess toluene, and repeat 3 times to obtain rheinyl chloride.

[0065] 0.436 grams of rhein chloride was added to the reaction flask, 20 milliliters of dichloromethane was added, stirred, 2 milliliters of absolute ethanol and 0.5 milliliters of triethylamine were added at room temperature, and the reaction was carried out at room temperature. TLC followed the reaction (ethyl acetate:petroleum Ether = 1:2), after 32 hours, there was no significant change in the system, the solvent was evaporated under reduced pressure, separated by column chromatography, and 17 mg of yellow solid was obtained, with a yield of 7.7%.

[0066] 1H NMR (400 MHz, d6-DM...

Embodiment 2

[0067] Embodiment two: the synthesis of methoxy pentyl rhein

[0068] Add 0.22 g of rhein into the reaction flask, add 100 ml of dichloromethane, add 5 ml of thionyl chloride under stirring, and react overnight under reflux until the system is dissolved. Evaporate the solvent under reduced pressure to dryness, add 5 ml of toluene to remove the excess toluene, and repeat 3 times to obtain rheinyl chloride.

[0069] Add 0.40 g of rhein to the reaction flask, add 20 ml of dichloromethane, stir, add 2 ml of n-amyl alcohol and 0.5 ml of triethylamine at room temperature, react at room temperature, follow the reaction by TLC (ethyl acetate:petroleum ether =1:2), after 32 hours, there was no significant change in the system, the solvent was evaporated under reduced pressure, separated by column chromatography, and 0.0525 g (0.148 mmol) of a yellow solid was obtained.

[0070] Add 0.0525 grams of n-pentyl rhein to the reaction flask, add 5 milliliters of dioxane, stir to dissolve, ad...

Embodiment 3

[0072] Embodiment three: the synthesis of rhein amide

[0073] Add 20 ml of anhydrous methanol to the reaction flask, add 2 ml of thionyl chloride dropwise under ice bath, after dropping, keep warm for 1 hour, add 1.3653 g of arginine, raise to room temperature, react for 4 hours, and heat up to 50°C , reacted for 16 hours, evaporated the arginine methyl ester of the solvent under reduced pressure.

[0074] Add 0.338 g of rhein to the reaction flask, add 0.2027 g of DCC, 0.1525 g of DMAP, 0.235 g of L-arginine methyl ester, and 20 ml of 1,2-dichloromethane, stir, heat up to 80°C, and keep warm for 23 hour, evaporate the solvent under reduced pressure, add 20 ml of anhydrous methanol to the residue, stir, filter off insoluble matter, evaporate most of the solvent from the filtrate under reduced pressure, filter with suction, and wash the filter cake with ether to obtain a yellow solid, which after drying Obtained 0.0738 grams of product, yield 13.7%.

[0075] 1H NMR (400 MHz,...

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Abstract

The invention relates to the synthesis of an emodin compound illustrated in the formula (I), and the application of the compound in antimicrobial and anti-tumor agents. The result of the in-vitro antibacterial activity test shows that, a synthesized emodin derivative is strong in antimicrobial activity for methicillin-resistant staphylococcus aureus ATCC25923, escherichia coli ATCC25922, Pseudomonas aeruginosa ATCC27853, and helicobacter pylori. Therefore, the synthesized emodin derivative can be used for preparing antibacterial agents. The result of the in-vitro anti-tumor activity test shows that, the synthesized emodin derivative is strong in anti-tumor activity. Through exploring the influence of the emodin derivative on the croton oil-caused auricular swelling condition of mice, the above compound is good in anti-inflammatory activity. The chemical structural formula of the above emodin derivative is illustrated in the formula (I) as follows, wherein R1, R2 and R3 are defined in the specification.

Description

technical field [0001] The present invention relates to an antibacterial, antitumor, anti-inflammatory compound, a composition containing the compound and applications thereof, in particular to rhein derivatives, rhein derivatives, diacerein derivatives, and aloe-emodin derivatives And the composition containing the derivative and its application in antibacterial, antitumor and antiinflammatory drugs. Background technique [0002] Emodin has a wide range of pharmacological effects (see: Advances in Pharmacy, 2005, 29 (12): 540-544; Chinese Pharmacology Bulletin, 2003, 19 (8): 851-854), and can inhibit tumor cell proliferation and metastasis (Life Sci, 1997, 61 (23): 2335-2344; Jpn J Cancer R, 2002, 93 (8): 874-882; Armed Police Medicine, 2004, 15 (7): 545-546; Phytochemist ry, 2001, 58( 8) : 1213-1217.), antibacterial, anti-inflammatory, inhibit liver and kidney fibrosis, dilate blood vessels and diuresis (Eur J Pharmacol, 1991 , 205 (3): 289-294), etc., have good clinical ...

Claims

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Application Information

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IPC IPC(8): C07C251/48C07C249/08C07C337/08C07C303/32C07C309/24C07C231/02C07C235/84C07C67/14C07C69/76C07C50/34C07C46/00A61K31/122A61K31/175A61K31/185A61K31/166A61K31/216A61K31/15A61P29/00A61P35/00A61P31/04A61P31/10
CPCY02A50/30
Inventor 刘进兵王子厚李忠野
Owner SHAOYANG UNIV
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