Sphaelactone derivatives, their pharmaceutical compositions, preparation method thereof and application thereof
A technology of derivatives and lactones, applied in the preparation of anti-cancer or auxiliary anti-cancer drugs, the field of pharmaceutical compositions for the treatment of cancer or adjuvant treatment of tumors, can solve the problems of drug resistance, insensitivity of tumor stem cells, etc., and achieve strong Inhibitory effect
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[0038]Example 1:
[0039] Preparation of 11βH, 13-dimethylaminosmilide (compound 1, the structural formula is as follows (II))
[0040]
[0041] Lactone (106mg, 0.40mmol), triethylamine (2.0mL), methanol (30mL) were added to a 100mL round-bottom flask, heated to reflux for 3 hours, concentrated under reduced pressure, and subjected to silica gel column chromatography (petroleum ether:ethyl acetate) Ester:triethylamine=50:50:0.5) to obtain 107.4 mg of white solid, yield: 86%.
[0042] Molecular formula: C 17 H 27 NO 3
[0043] Molecular weight: 293
[0044] Appearance: White amorphous powder
[0045] Spectral data:
[0046] 1 H NMR (CDCl 3 , 400MHz)δ3.76(t, J=10.0Hz, 1H), 2.96(s, 1H), 2.49-2.67(m, 3H), 2.28-2.34(m, 1H), 2.30-2.34(m, 2H) , 2.18(s, 6H), 2.09(brs, 2H), 1.96(d, J=11.2, 1H), 1.67-1.73(m, 2H), 1.60(s, 3H) 1.22(brs, 3H), 1.18 (br s, 2H); 13 C NMR (CDCl 3 , 100MHz) δ177.0, 131.8, 131.3, 84.0, 80.2, 58.3, 58.1, 50.9, 46.0, 44.6, 38.4, 35.3, 30.0, 27.2, 2...
Example Embodiment
[0047] Example 2
[0048] Preparation of 4-propionyl lagalactone (compound 2, the structural formula is as follows (III))
[0049]
[0050] Lactone (106 mg, 0.40 mmol), triethylamine (2.0 mL), propionyl chloride (0.2 mL), and 5 mL of dichloromethane were added to a 20 mL round-bottomed flask, and the reaction was stirred at room temperature for 24 h, concentrated under reduced pressure, and layered on a silica gel column. Precipitated (petroleum ether:ethyl acetate=90:10) to obtain 87 mg of white solid, yield: 72%. Structural data of the prepared 4-propionyl lagalactone:
[0051] Molecular formula: C 18 H 24 NO 4
[0052] Molecular weight: 304
[0053] Appearance: White amorphous powder
[0054] Spectral data:
[0055] 1 H NMR (CDCl 3 , 400MHz)δ6.14(s, 1H), 5.42(s, 1H), 3.74(t, J=10.0Hz, J=10.0Hz, 1H), 1.80-2.74(m, 12H), 1.67(s, 3H) ), 1.50(s, 3H), 1.07(t, J=4.0Hz, 3H); 13 C NMR (CDCl 3 , 100MHz) δ173.8, 170.1, 139.5, 131.5, 130.4, 118.6, 88.4, 83.0, 56.6, 50.1...
Example Embodiment
[0056] Example 3
[0057] The synthetic method of 1,10-epoxy lagalactone (compound 3, structural formula is following formula (IV)):
[0058]
[0059] Lactone (106mg, 0.40mmol), m-chloroperoxybenzoic acid (0.45mmol), and 5mL of dichloromethane were added to a 20mL round-bottomed flask, and the reaction was stirred at room temperature for 6h, concentrated under reduced pressure, and subjected to silica gel column chromatography (petroleum ether). : ethyl acetate = 80: 20) to obtain 96 mg of white solid, yield: 91%. Structural data of the prepared 1,10-epoxy laurolactone:
[0060] Molecular formula: C 15 H 20 NO 4
[0061] Molecular weight: 264
[0062] Appearance: White amorphous powder
[0063] Spectral data:
[0064] 1 H NMR (CDCl 3 , 400MHz)δ6.13(d, J=3.2Hz, 1H), 5.44(d, J=2.8Hz, 1H), 3.73(t, J=10.4Hz, 1H), 1.30-2.46(m, 11H), 1.29(s, 3H), 1.28(s, 3H); 13C NMR (CDCl3, 100MHz) δ 168.7, 137.8, 118.6, 79.2, 77.3, 74.2, 66.7, 52.6, 48.4, 37.1, 33.8, 29.0, 24.6, 22.5...
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