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A kind of chroman derivative and its preparation method and application
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A derivative, chroman technology, applied in the field of pharmacy, to achieve the effects of novel structure, improvement of intestinal microecological disorder, and excellent anti-alcoholic fatty liver disease activity in vivo
Active Publication Date: 2021-08-10
CHINA PHARM UNIV
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[0005] At present, the research on ACC inhibitors at home and abroad is in the clinical and preclinical research stage, and no drug has been approved for marketing. It is necessary to study compounds with more diverse structural types to obtain ideal drugs.
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[0088] Put 8g (52.80mmol) of 2,4-dihydroxyacetophenone and 150mL of 1,4-dioxane into a 250mL three-necked flask, and stir at room temperature until completely dissolved. Add 11.20 mL (0.11 mol) borontrifluorideether solution drop by drop, and stir at room temperature until the solution turns pink. Then, 7.19 g (0.11 mol) of isoprene in 1,4-dioxane (25 mL) was added dropwise, and the solution turned purple-black, and stirred overnight at room temperature. After the reaction was detected by TLC, saturated ammoniumchloride solution (50mL) was added to the reaction solution, extracted with ethyl acetate (60mL×3), the organic phases were combined, and the organic phase was washed with saturated sodiumchloride solution (50mL). It was dried over sodium sulf...
[0099] The synthesis procedure was the same as in Example 1, and 69 mg of white solid was obtained, with a melting point of 219-221° C. and a yield of 77%.
[0100] 1 H NMR (300MHz, DMSO-d 6 )δ13.05(s,1H),8.35–8.21(m,1H),7.87–7.69(m,3H),7.60(d,J=9.1Hz,3H),7.50(s,1H),7.25(d ,J=8.3Hz,1H),6.34(s,1H),4.21(s,2H),3.69(s,2H),2.81–2.64(m,4H),1.92(s,2H),1.84–1.71( m,4H),1.29(s,6H).MS(ESI)m / z: calculated for C 32 h 31 N 3 o 4 [M-H] - :520.2, found: 520.2.
[0104] The synthesis steps were the same as in Example 1, and 70 mg of white solid was obtained, with a melting point of 175-177° C. and a yield of 70%.
[0105] 1 H NMR (300MHz, DMSO-d 6 )δ12.19(s,1H),7.49(s,1H),7.34(s,1H),6.98(s,1H),6.33(s,1H),4.17(s,2H),2.80(t,J =7.5Hz,2H),2.72(d,J=8.9Hz,4H),2.49(s,3H),2.01–1.63(m,8H),1.29(s,6H),0.94(t,J=7.4Hz ,3H).MS(ESI)m / z: calculated for C 30 h 35 N 3 o 4 [M+Na] + :524.3,found:524.3.
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Abstract
The invention discloses a chroman derivative, the structure of which is shown in formula (I): the chroman derivative provided by the invention has a novel structure, excellent ACC inhibitory activity and in vivo anti-nonalcoholic fatty liver disease activity , and can significantly reduce the transcription of fatty acidde novo synthesis genes, inflammation-related genes, and liver fibrosis-related genes; it can also improve the disturbance of intestinal microecology induced by high-fat food. The chroman derivative and its pharmaceutically acceptable salt can be used to treat or prevent non-alcoholic fatty liverdisease, alcoholic fatty liverdisease and metabolic syndrome, exhibit excellent drug safety, and have broad development prospects.
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