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Spiro [benzo [c] aza-1, 1 '-cyclohexyl]-3-ketone compound

A ketone compound, cyclohexyl technology, applied in the field of medicine, to achieve the effects of optimizing synthesis steps, good anti-proliferation ability, and improving anti-tumor effect

Active Publication Date: 2021-06-11
中国医科大学
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  • Claims
  • Application Information

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Problems solved by technology

Therefore, this patent designs a new anti-tumor compound based on the natural plant-Erythrina alkaloid, and combines the structural characteristics of the anti-tumor compound designed by our team in the past, optimizes the seven-membered ring structure, in order to obtain a new anti-tumor effect compound, no reports of related structures have been seen in the prior art

Method used

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  • Spiro [benzo [c] aza-1, 1 '-cyclohexyl]-3-ketone compound

Examples

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Effect test

Embodiment 1

[0050] Example 1 Preparation of 7-phenyl-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one (A1).

[0051] a. Preparation of 1-phenylcyclohexanol.

[0052] Add bromobenzene (50 g, 0.31 mol) and magnesium strips (8.13 g, 0.33 mol) into a 1000 mL 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 solution was added into saturated aqueous ammonium chloride solution, extracted with ether, the extract was dried and evaporated under reduced pressure to obtain the product, yield: 97.0%.

[0053] b. Preparation of 1-azido-1-phenylcyclohexane.

[0054] 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...

Embodiment 2

[0066] Example 2 Preparation of 7-(2-chlorophenyl)-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one (A2).

[0067] The preparation of 7-bromo-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one is as in Example 1f, using o-chlorophenylboronic acid as raw material, According to the steps of Example 1g, 7-(2-chlorophenyl)-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one (A2 ), brown solid, yield: 83.1%.

[0068] 1 H NMR (600MHz, DMSO-d 6 )δ7.51(d, J=7.8Hz, 3H), 7.46–7.39(m, 4H), 4.70(d, J=6.3Hz, 2H), 4.50(d, J=3.8Hz, 2H), 2.20( m,2H),2.14–2.06(m,2H),1.86–1.75(m,4H),1.30–1.24(m,2H); 13 C NMR (150MHz, DMSO-d 6 )δ 165.40, 144.48, 140.84, 138.96, 137.45, 131.85, 131.53, 129.44, 128.86, 126.94, 126.76, 126.19, 125.59, 57.64, 35.40, 32.16, 25.55, 24.924, 21.

Embodiment 3

[0069] Example 3 Preparation of 7-(3-chlorophenyl)-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one (A3).

[0070] The preparation of 7-bromo-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one is as in Example 1f, using m-chlorophenylboronic acid as raw material, According to the steps of Example 1g, 7-(3-chlorophenyl)-4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3(2H)-one (A3 ), brown solid, yield: 84.0%.

[0071] 1 H NMR (600MHz, DMSO-d 6 )δ7.46–7.42(m,4H),7.32(t,J=7.3Hz,3H),5.91(s,2H),5.70(s,2H),1.68–1.59(m,9H),1.29(d ,J=5.2Hz,1H); 13 C NMR (150MHz, DMSO-d 6 )δ 167.40, 148.02, 144.18, 138.69, 132.90, 129.97, 127.75, 127.64, 126.47, 125.85, 125.14, 124.84, 57.79, 35.31, 28.63, 26.85, 24.91, 21.84.

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Abstract

The invention belongs to the technical field of medicines, relates to a compound with anti-tumor activity and a specific chemical structure, and particularly relates to a 4, 5-dihydrospiro [benzo [c] aza-1, 1 '-cyclohexyl]-3 (2H)-ketone compound as well as a preparation method and application of the 4, 5-dihydrospiro [benzo [c] aza-1, 1'-cyclohexyl]-3 (2H)-ketone compound. The structural general formula of the compound is shown in the specification, wherein an R group on an a benzene ring is substituted by a 2-position, 3-position or 4-position monosubstituted fluorine atom, methyl, chlorine atom, methoxyl, bromine atom or hydrogen atom. Pharmacological studies show that the compound provided by the invention has certain inhibitory activity on human colon cancer HCT-116 cells, can be used for preparing antitumor drugs, and opens up a new way for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

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, in particular to 4,5-dihydrospiro[benzo[c]azepine-1,1'-cyclohexyl]-3( 2H)-ketone compounds and their preparation methods and uses. Background technique [0002] Cancer is a serious public health problem worldwide. Most cancer patients lose their lives due to high mortality and high 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. 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, this patent designs a new anti-tumor compound based on the natural plant-Erythrina alkaloid, and combines the s...

Claims

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Application Information

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IPC IPC(8): C07D223/14A61K31/55A61P35/00
CPCC07D223/14A61P35/00
Inventor 孟繁浩李帅薛文涵钱欣画朱菊李馨阳刘凯利王德普
Owner 中国医科大学
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