Dihydrobenzopyrans ketone compound and uses thereof
A compound, dihydrogen technology, applied in the field of medicine, can solve the problem of unclear function of non-classical estrogen membrane signaling pathway
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Embodiment 1
[0043] Example 1: (S)-2,3-dihydro-7-hydroxyl-2-(4-hydroxyphenyl)-6-[2-(1-pyrrolidinyl)ethyl]-4H-1-benzene Preparation of pyran-4-one (compound 1)
[0044]
[0045] Preparation of Compound B
[0046] Compound A (320 mg, 1.0 mmol) was dissolved in 20 ml of methanol at -78°C, and then ozone was passed through for 20 minutes. Remove the cooling bath, then add 0.5 mL dimethyl sulfide to the above mixture, and stir for 10 minutes. After removing the solvent, the product was separated by column chromatography to obtain product B (260 mg, 88%).
[0047] Preparation of Compound 1
[0048] A mixture of compound B (250mg, 0.71mmol), pyrrolidine hydrochloride (252mg, 2.34mmol), sodium acetate (107mg, 1.30mmol), sodium cyanoborohydride (80mg, 1.28mmol) and methanol (4mL) at room temperature Stirring was continued for 5 hours. Then 5 ml of water was added to the above mixture and stirred for 30 minutes. Then the above mixture was extracted with ethyl acetate (3×10 mL). The extract...
Embodiment 2
[0049] Example 2: (S)-2,3-dihydro-7-hydroxyl-2-(4-hydroxyphenyl)-6-[2-(dimethylamino)ethyl]-4H-1-benzo Preparation of pyran-4-one (compound 2)
[0050]
[0051] A mixture of compound B (120 mg, 0.34 mmol), dimethylamine hydrochloride (65 mg, 0.80 mmol), sodium acetate (43 mg, 0.52 mmol), sodium cyanoborohydride (32 mg, 0.51 mmol) and methanol (2 mL) Stir at room temperature for 8 hours. Then 5 ml of water was added to the above mixture and stirred for 30 minutes. Then the above mixture was extracted with ethyl acetate (3×10 mL). The extracts were combined and dried over anhydrous sodium sulfate. After removing the solvent, the crude product was purified by column chromatography to obtain the product compound 1 (45 mg, 41%). 1 H NMR (acetone-d6, 300MHz): δ7.48(s, 1H), 7.37((d, J=8.1Hz, 1H), 6.89(d, J=8.7Hz, 1H), 6.23(s, 1H) , 5.37 (dd, J 1 =2.7Hz,J 2 =12.6Hz, 1H), 2.96(dd, J 1 =12.8Hz,J 2 =16.7Hz, 1H), 2.84-2.80(m, 1H), 2.74-2.72(m, 1H), 2.62(dd, J 1 =2.9Hz,J 2 =16...
Embodiment 3
[0052] The in vitro biological test of embodiment 3 formula (I) compound
[0053] Test 3-1:
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