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Usnea nicotinamide compound and its preparation method and application

A technology of usnea nicotinamide and its compound, which is applied in the field of usnea nicotinamide compound and its preparation, can solve the problems of uncertain curative effect, large toxic and side effects of drugs, and poor selectivity, and achieve simple and rapid synthesis steps, easy-to-obtain raw materials, and high-quality products. easy effect

Active Publication Date: 2022-05-03
KUNMING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the cancer chemotherapy drugs currently used clinically have many problems such as large toxic and side effects, uncertain curative effect, poor selectivity, weak targeting, and drug resistance of cancer cells, which make the clinical application and effect of cancer chemotherapy treatment limited. very restrictive

Method used

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  • Usnea nicotinamide compound and its preparation method and application
  • Usnea nicotinamide compound and its preparation method and application
  • Usnea nicotinamide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Usnea nicotinamide compound of the present invention: N-[1-(6-acetyl-7,9-dihydroxy-8,9-dimethyl-1,3-dioxo-3,9b-dihydro-1H- Diphenylfuran-2-ethyl)-ethyl]-isonicotinamide (English structural name: N-[1-(6-Acetyl-7,9-dihydroxy-8,9-dimethyl-1,3-dioxo- 3,9b-dihydro-1H-dibenzofuran-2-yliden)-ethyl]-isonicoyinamide) chemical synthesis and structure identification.

[0053] Usnemine (C 18 h 17 NO 6 ) and niacin (C 6 h 5 NO 2 ) as a substrate, under the action of dehydrating agent DIC and catalyst DMAP, the chemical synthesis reaction is carried out in an organic solvent medium. The results of the orthogonal test show that, with dichloromethane solvent as the medium, usnemine: niacin=1:1.5 (mol ratio), usnemine: DMAP=1:0.2 (mol ratio), usnemine: DIC= 1:0.1 (molar ratio), room temperature reaction, reaction time 96 hours is the best, high product yield, less impurities, easy to purify. The product yield in other organic solvent media is low or cannot form usnenic acid ami...

Embodiment 2

[0065] A kind of usnea nicotinamide compound, the structural formula of described usnea nicotinamide is as shown in formula (I),

[0066]

[0067] The preparation method of described usnea nicotinamide compound, comprises the steps:

[0068] Add usnezone into the organic solvent, shake it thoroughly, and then ultrasonicate at room temperature for 10 minutes, then add nicotinic acid, DIC and DMAP and stir, then let it stand at room temperature for 48 hours, then add distilled water and stir for 30 minutes to fully neutralize the unreacted DIC , the reaction product is purified to obtain the usnenic acid amide compound shown in formula (I). The reaction formula is as follows:

[0069]

[0070] Wherein, the molar ratio of usnemine to nicotinic acid is 1:1; the ratio of the volume of the organic solvent used to usnemine is 5000ml:1.5mol; the molar ratio of usnemine to DMAP is 1:0.15.

[0071] The filtrate after filtering the reaction solution was evaporated to dryness, and...

Embodiment 3

[0073]A kind of usnea nicotinamide compound, the structural formula of described usnea nicotinamide is as shown in formula (I),

[0074]

[0075] The preparation method of described usnea nicotinamide compound, comprises the steps:

[0076] Add usnezone into the organic solvent, shake it thoroughly, and then ultrasonicate it at room temperature for 10 minutes, then add nicotinic acid, DIC and DMAP and stir, then let it stand for 60 hours at room temperature, then add distilled water and stir for 30 minutes to fully neutralize the unreacted DIC , the reaction product is purified to obtain the usnenic acid amide compound shown in formula (I). The reaction formula is as follows:

[0077]

[0078] Wherein, the molar ratio of usnemine to nicotinic acid is 1:2; the ratio of the volume of the organic solvent used to usnemine is 5000ml:2mol; the molar ratio of usnemine to DMAP is 1:0.2.

[0079] The filtrate after filtering the reaction solution was evaporated to dryness, and ...

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Abstract

The invention relates to a preparation method and application of an usnea nicotinamide compound, belonging to the technical field of medicinal chemistry. The structure of the compound is shown in formula (I):, formula (I); its preparation method is to use usnezone and nicotinic acid as substrates, in an organic solvent medium, with N,N'-diisopropyl carbon Diimide is a dehydrating agent and 4-dimethylaminopyridine is a catalyst, and the compound with significant anticancer activity is prepared by acylation reaction at room temperature. The raw material of the synthesis method is easy to obtain, the steps are simple and fast, and the product is easy to purify. The acute toxicity of Usnea Niacinamide by oral gavage in mice was classified as non-toxic, and the experimental dose had no obvious toxicity on animal survival, weight gain, organ development, liver and kidney tissue, blood biochemical and blood routine indicators. The compound of the invention has significant anti-tumor effect, can be used for preparing anti-tumor chemotherapeutic drugs and auxiliary anti-tumor health products, and has good application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a usnea nicotinamide compound and its preparation method and application. The structure of the compound is N-[1-(6-acetyl-7,9-dihydroxy-8,9-dimethyl -1,3-dioxo-3,9b-dihydro-1H-diphenylfuran-2-ethyl)-ethyl]-isonicotinamide (English structural name: N-[1-(6-Acetyl- 7,9-dihydroxy-8,9-dimethyl-1,3-dioxo-3,9b-dihydro-1H-dibenzofuran-2-yliden)-ethyl]-isonicoyinamide), the molecular formula is C 24 h 20 N 2 o 7 , with a molecular weight of 448. Background technique [0002] Malignant tumor is a major disease that seriously threatens human health and life safety. It has become the main cause of death of human beings and seriously threatens human health and life safety. According to data released by the International Cancer Institute of the World Health Organization in Globocan, there were 12.661 million new cancer cases and 7.564 million deaths worldwide in 2008. In 2012,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A61P35/00A61P35/02A23L33/10
CPCC07D405/12A61P35/00A61P35/02A23L33/10A23V2002/00A23V2200/308A23V2250/30
Inventor 贺小琼连文静尤雨桐
Owner KUNMING MEDICAL UNIVERSITY
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