Naringenin carbamate compound, preparation method and application thereof

Abstract

The invention discloses a naringenin carbamate compound, a preparation method and an application thereof, wherein the naringenin carbamate compound is characterized in that a chemical structure formula is represented as the formula (I); the naringenin carbamate compound can be used for preparing medicines for treating and / or preventing neurodegenerative diseases.

Description

technical field

[0001] The invention relates to the field of drug synthesis, in particular to a naringenin carbamate compound, its preparation method and application. Background technique

[0002] Alzheimer's disease (AD) is one of the diseases with the highest morbidity and mortality among the elderly. According to the "2015 Global Alzheimer's Report" released by Alzheimer's Disease International (ADI), more than 46 million people in the world suffered from dementia in 2015. It is predicted that by 2050, the world's There will be 131.5 million people suffering from dementia, and the incidence rate of dementia patients in China has reached 6.61%. With the prolongation of the average life expectancy, the disease has developed into a major burden on the society and the medical care system, and has brought heavy mental and economic pressure to the society, patients and their families. Therefore, it is of great significance to research and develop new drugs for the treatment o...

Examples

Embodiment 1

[0028] Add 2.0mmol of naringenin (1), 7mmol of (a), 10mmol anhydrous potassium carbonate and 50ml acetonitrile, after stirring evenly, heat up and reflux and stir for 12 hours (track the reaction process with TLC); Methane chloride was extracted three times, the organic layers were combined and washed with saturated sodium chloride, dried and filtered over anhydrous sodium sulfate, the naringenin carbamate compound (I-1) was evaporated to dryness under reduced pressure, and the residue was subjected to column chromatography After purification (dichloromethane: acetone = 100:1 v / v), the corresponding naringenin carbamate compound (I-1) was obtained with a yield of 67.3%. The purity of the obtained target objects was all greater than 97% as determined by HPLC.

[0029]

[0030] Target compound I-1: 1 H NMR 11.86(s, 1H), 7.41(d, J=8.4Hz, 2H), 7.15(d, J=6.4Hz, 2H), 6.34(s, 2H), 5.39(d, J=12.4Hz, 1H ),3.47-3.36(m,4H),3.08-2.95(m,7H),2.81(d,J=14.8Hz,1H),1.25-1.15(m,6H). 13 C...

Embodiment 2

[0032] Add 2.0mmol of naringenin (1), 7mmol of 10mmol of anhydrous potassium carbonate and 50ml of acetonitrile, after stirring evenly, heated and refluxed and stirred for 12 hours (the reaction process was followed by TLC); After extraction, the organic layers were combined and washed with saturated sodium chloride, dried and filtered over anhydrous sodium sulfate, the naringenin carbamate compound (I-2) was evaporated to dryness under reduced pressure, and the residue was purified by column chromatography (dichloro Methane: acetone=100:1v / v), the corresponding naringenin carbamate compound (I-2) was obtained with a yield of 61.3%. The purity of the obtained target objects was all greater than 97% as determined by HPLC.

[0033]

[0034] Target compound I-2: 1 H NMR 11.84(s,1H),7.43(d,J=8.0Hz,2H),7.19(d,J=6.4Hz,2H),6.35(d,J=6.4Hz,2H),5.44(d,J =12.0Hz,1H),3.40-3.36(m,8H),3.08(d,J=13.6Hz,1H),2.85(d,J=15.6Hz,1H),1.28-1.20(m,12H).

Embodiment 3

[0036] Add 2.0mmol of naringenin (1), 7mmol of 10mmol of anhydrous potassium carbonate and 50ml of acetonitrile, after stirring evenly, heated and refluxed and stirred for 12 hours (the reaction process was followed by TLC); After extraction, the organic layers were combined and washed with saturated sodium chloride, dried and filtered over anhydrous sodium sulfate, the naringenin carbamate compound (I-3) was evaporated to dryness under reduced pressure, and the residue was purified by column chromatography (dichloro Methane: acetone=100:1v / v), the corresponding naringenin carbamate compound (I-3) was obtained with a yield of 52.6%. The purity of the obtained target objects was all greater than 97% as determined by HPLC.

[0037]

[0038] Target compound I-3: 1 H NMR 11.76(s, 1H), 7.35(d, J=8.0Hz, 2H), 7.09(d, J=8.0Hz, 2H), 6.27(s, 2H), 5.35(d, J=13.2Hz, 1H ),3.03(s,3H),2.98(s,3H),2.98(s,3H),2.98-2.96(m,1H),2.92(s,3H),2.77(d,J=17.2Hz,1H) .

technical field

[0001] The invention relates to the field of drug synthesis, in particular to a naringenin carbamate compound, its preparation method and application. Background technique

[0002] Alzheimer's disease (AD) is one of the diseases with the highest morbidity and mortality among the elderly. According to the "2015 Global Alzheimer's Report" released by Alzheimer's Disease International (ADI), more than 46 million people in the world suffered from dementia in 2015. It is predicted that by 2050, the world's There will be 131.5 million people suffering from dementia, and the incidence rate of dementia patients in China has reached 6.61%. With the prolongation of the average life expectancy, the disease has developed into a major burden on the society and the medical care system, and has brought heavy mental and economic pressure to the society, patients and their families. Therefore, it is of great significance to research and develop new drugs for the treatment o...

Examples

Embodiment 1

[0028] Add 2.0mmol of naringenin (1), 7mmol of (a), 10mmol anhydrous potassium carbonate and 50ml acetonitrile, after stirring evenly, heat up and reflux and stir for 12 hours (track the reaction process with TLC); Methane chloride was extracted three times, the organic layers were combined and washed with saturated sodium chloride, dried and filtered over anhydrous sodium sulfate, the naringenin carbamate compound (I-1) was evaporated to dryness under reduced pressure, and the residue was subjected to column chromatography After purification (dichloromethane: acetone = 100:1 v / v), the corresponding naringenin carbamate compound (I-1) was obtained with a yield of 67.3%. The purity of the obtained target objects was all greater than 97% as determined by HPLC.

[0029]

[0030] Target compound I-1: 1 H NMR 11.86(s, 1H), 7.41(d, J=8.4Hz, 2H), 7.15(d, J=6.4Hz, 2H), 6.34(s, 2H), 5.39(d, J=12.4Hz, 1H ),3.47-3.36(m,4H),3.08-2.95(m,7H),2.81(d,J=14.8Hz,1H),1.25-1.15(m,6H). 13 C...

Embodiment 2

[0032] Add 2.0mmol of naringenin (1), 7mmol of 10mmol of anhydrous potassium carbonate and 50ml of acetonitrile, after stirring evenly, heated and refluxed and stirred for 12 hours (the reaction process was followed by TLC); After extraction, the organic layers were combined and washed with saturated sodium chloride, dried and filtered over anhydrous sodium sulfate, the naringenin carbamate compound (I-2) was evaporated to dryness under reduced pressure, and the residue was purified by column chromatography (dichloro Methane: acetone=100:1v / v), the corresponding naringenin carbamate compound (I-2) was obtained with a yield of 61.3%. The purity of the obtained target objects was all greater than 97% as determined by HPLC.

[0033]

[0034] Target compound I-2: 1 H NMR 11.84(s,1H),7.43(d,J=8.0Hz,2H),7.19(d,J=6.4Hz,2H),6.35(d,J=6.4Hz,2H),5.44(d,J =12.0Hz,1H),3.40-3.36(m,8H),3.08(d,J=13.6Hz,1H),2.85(d,J=15.6Hz,1H),1.28-1.20(m,12H).

Embodiment 3

[0036] Add 2.0mmol of naringenin (1), 7mmol of 10mmol of anhydrous potassium carbonate and 50ml of acetonitrile, after stirring evenly, heated and refluxed and stirred for 12 hours (the reaction process was followed by TLC); After extraction, the organic layers were combined and washed with saturated sodium chloride, dried and filtered over anhydrous sodium sulfate, the naringenin carbamate compound (I-3) was evaporated to dryness under reduced pressure, and the residue was purified by column chromatography (dichloro Methane: acetone=100:1v / v), the corresponding naringenin carbamate compound (I-3) was obtained with a yield of 52.6%. The purity of the obtained target objects was all greater than 97% as determined by HPLC.

[0037]

[0038] Target compound I-3: 1 H NMR 11.76(s, 1H), 7.35(d, J=8.0Hz, 2H), 7.09(d, J=8.0Hz, 2H), 6.27(s, 2H), 5.35(d, J=13.2Hz, 1H ),3.03(s,3H),2.98(s,3H),2.98(s,3H),2.98-2.96(m,1H),2.92(s,3H),2.77(d,J=17.2Hz,1H) .

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