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Thymol ester derivatives, its preparation method and application thereof

A technology of drugs and compounds, applied in the preparation of carboxylate esters, cyanide reaction preparations, organic compounds, etc., can solve the problems of fast metabolism, low drug efficacy, high toxicity, etc.

Active Publication Date: 2012-10-17
吉林亚泰永安堂药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, thymol, the active ingredient of traditional Chinese medicine, has more or less certain defects in pharmacodynamics and pharmacokinetics, mainly including low drug efficacy, high toxicity, or too fast and too slow metabolism in the body, etc.

Method used

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  • Thymol ester derivatives, its preparation method and application thereof
  • Thymol ester derivatives, its preparation method and application thereof
  • Thymol ester derivatives, its preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of thymol succinyl ester:

[0020]

[0021] Weigh thymol (0.52 g, 3.4 mmol) and succinic anhydride (0.92 g, 8.37 mmol) into a 100 mL three-necked flask equipped with a stirring device, add pyridine (20 mL), react at 75 ° C for 6 h, and detect the reaction by TLC [V (ethyl acetate): V (petroleum ether) = 4: 1 is the developer], after the reaction is basically completed, cool to room temperature. Remove pyridine by rotary evaporation under reduced pressure, add 20 mL of water, extract with ether 50 mL×3, combine the ether layers, wash with water (10 mL×3), dry with anhydrous sodium sulfate, recover ether under reduced pressure to obtain a yellow oily liquid, Add 50 mL of ether and 20 mL of ice water, let stand for 30 min, separate and collect the organic phase, extract the water phase twice with 20 ml of ether, combine the organic phases, add anhydrous Na 2 SO 4 (5 g) dried overnight. The organic solvent was recovered under reduced pressure to obtain a ...

Embodiment 2

[0023] Preparation of Thymol Glycyl Ester

[0024]

[0025] In a 100 mL round-bottomed flask with a tail gas absorption device, add fluorenylmethoxycarbonyl glycine (4.9 g, 16.4 mmol), dichloromethane (30 mL), oxalyl chloride (15 mL). Heat to reflux and stir for 3 hours, evaporate under reduced pressure to remove the remaining oxalyl chloride to obtain fluorenylmethoxycarbonylglycyl chloride (F-moc-glycyl chloride) as a yellow solid.

[0026] Thymol (0.5 g, 3.3 mmol), pyridine (20.0 mL), and DMAP (0.05 g) were added to a 150 mL three-necked flask, and added dropwise at room temperature under stirring conditions to generate F-moc-glycyl chloride and toluene (20mL) mixed solution, after the dropwise addition, heated to 55°C, continued to react for 6 h, and monitored the reaction by TLC [developer: petroleum ether-ethyl acetate = 6:1, V / V]. After the basic reaction of the raw materials is complete, the toluene is distilled off under reduced pressure, the residue is dissolved ...

Embodiment 1 and Embodiment 2

[0030] Embodiment 1 and embodiment 2 compound show good antibacterial activity in in vitro antibacterial experiment:

[0031] Strains: 1 strain of Staphylococcus aureus (standard strain ATCC6538), 1 strain of Escherichia coli (standard strain ATCC8099), 1 strain of typhoid bacillus, 1 strain of paratyphoid bacillus, 1 strain of Shigella dysenteriae and more than 5 strains. Medium: Nutrient agar (NA) lot number: 20101216; nutrient broth (NB) lot number: 20100806; product number: HB1019, manufacturer Qingdao Shangkeyuan Haibo Biological Co., Ltd. Preparation of test bacteria solution : Inoculate 5 kinds of bacterial strains into nutrient agar medium respectively. Cultivate at 37°C for 24 hours to select standard colonies and transplant them into liquid nutrient broth medium. After culturing at 37°C for 6 hours, adjust the bacterial concentration to 10 by McFarland Turbidimetry 8 cFu / ml for later use. Dissolution of the test drug: 2 solid compound monomers were dissolved s...

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Abstract

The invention relates to the field of pharmaceutical chemistry, specifically to thymol ester compounds (I), its preparation method and an application thereof. It is proved through a pharmacology experiment that the thymol ester compounds (I) provided by the invention can be used to prepare medicines for treating or preventing diseases caused by bacteria or diseases caused by fungi and can be also used to prepare animal feed additives or drinking water tonifying formula for treating, mitigating or preventing necrotic enteritis caused by Shigella species, clostridium and Clostridium perfringens. The invention also discloses a preparation method of the derivatives and their pharmaceutical composition.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of thymol ester compounds, which can be used to treat or prevent diseases caused by bacteria or fungi. The invention also discloses a preparation method thereof and a pharmaceutical composition thereof. Background technique [0002] The advent of penicillin ushered in the magical era of antibiotics, and various human diseases caused by bacterial infections can be completely treated by antibiotics within a period of time. Since the 20th century, with the development of science and technology, research on antibacterial drugs such as sulfonamides, penicillins, aminoglycosides, chloramphenicol, tetracyclines, and macrolides has developed rapidly, especially semi-synthetic penicillins and cephalosporins. The advent of antibacterial drugs such as antibiotics, new β-lactams, and quinolones has made it possible to effectively treat various bacterial infections, and has made out...

Claims

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Application Information

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IPC IPC(8): C07C69/40C07C67/08C07C227/20C07C229/08A61K31/225A61K31/223A61P31/04A61P31/10A23K1/16
CPCY02A50/30
Inventor 栗进才黄鹏牛倩
Owner 吉林亚泰永安堂药业有限公司
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