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Azabicyclo[3.2.1]oct-3-one compounds and their preparation methods and uses

A ketone compound, azabicycle technology, applied in the field of medicine, can solve the problems of strong neurotoxicity and cardiotoxicity, limited clinical application, etc., and achieve the effect of simplifying the synthesis steps

Active Publication Date: 2021-04-20
中国医科大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, aconitine alkaloids have strong neurotoxicity and cardiotoxicity, and direct drug use is limited in clinical applications

Method used

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  • Azabicyclo[3.2.1]oct-3-one compounds and their preparation methods and uses
  • Azabicyclo[3.2.1]oct-3-one compounds and their preparation methods and uses
  • Azabicyclo[3.2.1]oct-3-one compounds and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime.

[0063] Add L-camphor (98.53mmol), hydroxylamine hydrochloride (158.30mmol), methanol (170mL) and water (70mL) into the reaction flask, and slowly add 50mL of water-soluble sodium acetate (237.71mmol) dropwise under stirring at 80°C. After the dissolution is complete, continue to heat up to 100°C, and reflux for 12 hours. After the reaction is complete, concentrate under reduced pressure to remove methanol, filter with suction, wash the filter cake with plenty of water, and dry naturally to obtain 14.8 g of white solid, yield: 93.1%.

Embodiment 2

[0065] Preparation of 1,8,8-trimethyl-2-azabicyclo[3.2.1]octan-3-one.

[0066] Add 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime (35.87mmol), triethylamine (107.62mmol) and 1,4-dioxane (80mL) into the reaction flask Add methanesulfonyl chloride (71.75mmol) of 1,4-dioxane (30mL) dropwise under stirring at -5°C, maintain the temperature for 10 minutes, take it out, add 50mL of 1,4-dioxane, and react at room temperature Overnight, the reaction was complete, diluted with water, extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain 1.26 g of refined product, yield: 21.0%.

Embodiment 3

[0068] Preparation of 1,8,8-trimethyl-2-(prop-2-yn-1-yl)-2-azabicyclo[3.2.1]octan-3-one.

[0069] Add 1,8,8-trimethyl-2-azabicyclo[3.2.1]oct-3-one (3.89mmol) and tetrahydrofuran (20mL) into the reaction flask, slowly add hydrogenation in batches under stirring at -5°C Sodium (4.66mmol), after maintaining the temperature for 30 minutes, take it out, add 3-bromopropyne (4.27mmol), react at room temperature overnight, the reaction is complete, add water to quench, extract with dichloromethane, wash with saturated saline, and dry over anhydrous sodium sulfate , and concentrated to dryness under reduced pressure to obtain 0.33 g of refined product, yield: 41.2%.

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Abstract

The invention discloses an azabicyclo[3.2.1]oct-3-one compound, a composition containing the compound and a preparation method thereof, belonging to the field of medicine. The present invention prepares L-camphor oxime by reacting with hydroxylamine with L-camphor as the starting material, reacts with propyne bromide through Beckman gravity, and finally obtains azabicyclo[3.2.1 ] octan-3-ketone compound. The azabicyclo[3.2.1]octane-3-one compound prepared by the invention has a novel structure and has remarkable effect in the antitumor activity test in vitro.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to an azabicyclo[3.2.1]octan-3-one compound, a composition containing the compound and a preparation method thereof. The present invention also relates to the application of these compounds and compositions in antitumor. Background technique [0002] Cancer is a malignant tumor originating from epithelial tissue. It is a disease characterized by rapid cell proliferation and metastasis. The death rate ranks first among all diseases. Cancer has biological characteristics such as abnormal cell differentiation and proliferation, uncontrolled growth, invasion and metastasis, and its occurrence is a multi-factor and multi-step complex process. According to the latest global cancer data released by the International Agency for Research on Cancer (IARC), there were 18.1 million new cancer cases and 9.6 million deaths worldwide in 2018, further increasing the global cancer burden. Lung cancer, female...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/08A61K31/55A61P35/00
CPCA61P35/00C07D487/08
Inventor 孟繁浩张毅张廷剑涂顺李馨阳王琳孙琦梁经纬赵楠
Owner 中国医科大学
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