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Isolongifolene alkyl oxazolone as well as synthesis method and application thereof

A technology of alkyl oxazolone and synthesis method, applied in the direction of drug combination, organic chemistry, non-central analgesics, etc., to achieve the effect of expanding the field of utilization

Active Publication Date: 2015-09-09
扬州胜宁信息技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Analysis of compounds from free sterol incubations of parasites suggests that these novel TZHs may act to inhibit ergosterol biosynthesis

Method used

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  • Isolongifolene alkyl oxazolone as well as synthesis method and application thereof
  • Isolongifolene alkyl oxazolone as well as synthesis method and application thereof
  • Isolongifolene alkyl oxazolone as well as synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0024] The synthetic method of isolongifolyl oxazolone, the steps are as follows:

[0025] 1) Condensation and substitution reaction between isolonganone and semicarbazide hydrochloride to generate semicarbazone.

[0026]

[0027] The specific operation is: in a 50mL three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser, add isolonganone (2mmol), semicarbazide hydrochloride (2mmol), and absolute ethanol 20mL in sequence, and heat and stir. After heating to reflux temperature, add an appropriate amount of concentrated sulfuric acid catalyst, and react for 12-24 hours (monitored by LC-MS). Continuously washed with sodium chloride for 5 times, dried over anhydrous sodium sulfate, filtered, rotary evaporated, recrystallized with 95% ethanol, and purified to obtain isolongifolyl semicarbazone.

[0028] 2) Cyclization reaction of semicarbazone compounds with ethyl bromoacetate (or ethyl chloroacetate) to generate corresponding thiazolone compo...

Embodiment 2

[0034] Inhibitory activity test of isolongifolyl oxazolones on the inflammatory response of human umbilical vein endothelial cells (HUVECs).

[0035] 1. Cell culture method: culture human umbilical vein endothelial cells in DMEM medium with 10% calf serum. Put in CO 2 in an incubator (37°C, 5% CO 2 , 95% air, maintain a certain humidity environment), and observe the growth of cells under an inverted microscope. According to the actual condition of the cells, change the medium; after 1-2 days of culture, the cells can become a monolayer, and then digested with 0.25% trypsin, and passaged at a ratio of 1:3. Human umbilical vein endothelial cells grown as monolayers were used during the experiments.

[0036] 2. Establishment and grouping of experimental models: First, cells were digested with 0.25% trypsin, and DMEM medium containing 10% calf serum was added. Use a dropper to blow into a single cell suspension, and inoculate the cells in a 96-well culture plate at a seeding d...

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Abstract

The invention discloses isolongifolene alkyl oxazolone as well as a synthesis method and an application thereof. The molecular formula of the isolongifolene alkyl oxazolone is C18H27N302, the molecular weight is 317.21, the physical state of the isolongifolene alkyl oxazolone is a white solid, and m.p. is 202 DEG C. The synthesis method comprises steps as follows: isolongifolanone is taken as a raw material and subjected to condensation through semicarbazide hydrochloride, and then semicarbazone is obtained; then the isolongifolene alkyl oxazolone is obtained through ring formation under the condition of reflux of absolute ethyl alcohol. The isolongifolene alkyl oxazolone shows good activity on inflammation elimination of cells and is a potential anti-inflammatory compound.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to an isolongifolyl oxazolone and a synthesis method and application thereof. Background technique [0002] Thiazole compounds are a class of important five-membered heterocyclic chemical substances containing nitrogen and sulfur. Due to their rich electrons, they are easy to form metal ion bonds, hydrogen bonds, and π-π, electrostatic and hydrophobic interactions. In the field of medicine, thiazole compounds can be used as drugs to show great research and development value, and have shown great potential in anti-tumor diseases, anti-fungal diseases, anti-cancer, anti-inflammatory and analgesic, anti-viral diseases, anti-parasites, and anti-oxidation. Development prospects. [0003] Due to its special biological activity and strong coordination ability, thiazolone has many medicinal activities such as bactericidal and antibacterial, anti-tumor, anti-inflammatory ...

Claims

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Application Information

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IPC IPC(8): C07D263/48A61P29/00
CPCC07D263/48
Inventor 王石发方伟蓉王朋娜韩丹杨益琴徐徐谷文蔡涛黄建峰曹晓琴芮坚丁志彬王芸芸杨金来吴承亮
Owner 扬州胜宁信息技术有限公司
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