7-azaspiro[5.6]dodecan-10-one compound and its preparation method and use

A ketone compound, azaspiro technology, applied in the field of medicine, can solve the problems of poor selection, drug resistance, large toxic and side effects, etc.

Active Publication Date: 2021-06-04
中国医科大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the current anti-tumor drugs have certain curative effects, there are still problems such as drug resistance, poor selection, and large toxic and side effects.

Method used

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  • 7-azaspiro[5.6]dodecan-10-one compound and its preparation method and use
  • 7-azaspiro[5.6]dodecan-10-one compound and its preparation method and use
  • 7-azaspiro[5.6]dodecan-10-one compound and its preparation method and use

Examples

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preparation example Construction

[0046] In order to achieve the above object, the present invention also provides a preparation method for the 7-azaspiro[5.6]dodecan-10-one compound, which specifically includes the following steps.

[0047] Step 1. Add 1 times the amount (molar amount) of bromobenzene and 0.5 times the amount of magnesium strips into the reaction bottle, dissolve them in an appropriate amount of ether, initiate at 35°C, and monitor the reaction progress by thin-layer chromatography. After the reaction was completed, 1.1 times the amount of cyclohexanone was added, and the reaction was carried out at 35° C. for 5 hours. After the reaction was completed, the reaction solution was added to aqueous ammonium chloride solution, extracted with ether, and the extract was dried and evaporated under reduced pressure to obtain 1-phenylcyclohexanol.

[0048] Step 2. Add 1-fold amount of 1-phenylcyclohexanol to the reaction flask, appropriate amount of dichloromethane as solvent, 2-fold amount of sodium a...

Embodiment 1

[0058] Preparation of 3,4-dihydrospiro[benzo[c]azepine-1,1'-cyclohexane]-5(2H)-one (A1).

[0059] a. Preparation of 1-phenylcyclohexanol.

[0060] Add bromobenzene (50g, 0.31mol) and magnesium strips (8.13g, 0.33mol) into a 1000mL three-necked flask, dissolve them in an appropriate amount of ether, and initiate at 35°C. After the reaction was completed, cyclohexanone (34.38 g, 0.35 mol) was added and reacted at 35° C. for 5 hours, and the reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the reaction liquid was added into a saturated aqueous ammonium chloride solution, extracted with ether, the extract was dried, and evaporated under reduced pressure to obtain the product with a yield of 95.5%.

[0061] b. Preparation of 1-azido-1-phenylcyclohexane.

[0062] Add 1-phenylcyclohexanol (20.00g, 0.11mol), 500mL of dichloromethane, sodium azide (8.11g, 0.12mol), trifluoroacetic acid (25.88g, 0.23mol) into a 1000mL reaction flask, at r...

Embodiment 2

[0074] 2-((1-Phenyl-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydrospiro[benzo[c]azepine-1,1'- Preparation of cyclohexane]-5(2H)-one (A2).

[0075] The preparation of 3,4-dihydrospiro[benzo[c]azepine-1,1'-cyclohexane]-5(2H)-one is as in Example 1.

[0076] a. 2-(Propyl-2-yn-1-yl)-3,4-dihydrospiro[benzo[c]azepine-1,1'-

[0077] Preparation of cyclohexane]-5(2H)-one.

[0078]Add 3,4-dihydrospiro[benzo[c]azepine-1,1'-cyclohexane]-5(2H)-one (1.00g, 0.004mol) and 50mL of acetonitrile into a 100mL reaction flask, Potassium carbonate (1.21 g, 0.009 mol), propyne bromide (0.57 g, 0.005 mol), heated to reflux at 85°C, and the reaction progress was monitored by thin-layer chromatography. After the reaction is complete, filter with suction, add an appropriate amount of water to the filtrate for extraction, dry the extract and evaporate under reduced pressure to obtain 2-(propyl-2-yn-1-yl)-3,4-dihydrospiro[benzo [c] Aza-1,1'-cyclohexane]-5(2H)-one.

[0079] b. Preparation of 1-azido-benzen...

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Abstract

The invention belongs to the field of medicine, and in particular relates to 7-azaspiro[5.6]dodecane-10-one compounds and their preparation methods and applications. The present invention synthesizes a seven-membered ring structure for the first time, and obtains a brand-new compound with more anti-tumor effect. No report on the relevant structure has been seen. Pharmacological studies have shown that the compound of the present invention is effective on human lung cancer A549 cells and human ovarian cancer OVCAR‑3 cells. It has a certain inhibitory activity and provides a basis for the subsequent preparation of antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a class of compounds with specific chemical structures having antitumor activity, specifically 7-azaspiro[5.6]dodecan-10-one compounds and their preparation methods and applications. Background technique [0002] Malignancy, also known as cancer, is a serious global public health problem. Most cancer patients lose their lives due to its high mortality and recurrence rates. It is characterized by the uncontrolled division and spread of abnormal cells in the body. Therefore, the synthesis of effective new anticancer drugs is one of the most important goals of modern medicinal chemistry. At this stage, the main way to treat cancer clinically is to use chemical drug therapy. Although the current anti-tumor drugs have certain curative effects, there are also problems such as drug resistance, poor selection, and large toxic and side effects. Therefore, many researchers at home and a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06A61K31/55A61P35/00
CPCA61P35/00C07D403/06
Inventor 孟繁浩李帅朱菊许海丽李馨阳王琳张廷剑梁经纬孙琦赵楠
Owner 中国医科大学
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