Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels
A technology of cinnamate and derivatives, applied in the preparation of carboxylate, preparations for skin care, preparation of organic compounds, etc., can solve the problem of insufficient tyrosinase inhibitory activity, unprovable safety, lack of cytotoxicity of compounds, etc. Cell experiments, etc.
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Embodiment 1
[0078] Synthesis of compound 1: (E)-3-(2-acetyl-5-methoxyphenoxy)propyl-3-(3-methoxy-4-(prop-1-en-2-yloxy base) phenyl) acrylate
[0079]
[0080] 1. Weigh 1.66g (10.0mmol) paeonol (compound I-1) and 0.83g (6.0mmol) K 2 CO 3 Place in a round bottom flask, add 100mL of acetone as a solvent, stir at room temperature for 0.5h, then add 2.08g (15.0mmol) of 3-bromo-1-propanol (compound II-1), heat to 80°C for 8h under reflux, After the reaction was completed, it was cooled to room temperature, the solvent was removed under reduced pressure, and purified by silica gel column chromatography to obtain 2.691 g of crystalline compound III-1 with a yield of 65%, m.p.56°C.
[0081] 2. Add 1.96g (10mmol) of compound IV-1 and 15mL of thionyl chloride to a round bottom flask, connect the exhaust gas absorption device, raise the temperature to 80°C, and heat up to 90°C to recover thionyl chloride after no gas is produced. , to obtain compound V-1.
[0082] 3. Under the conditions of ic...
Embodiment 2
[0084]Synthesis of compound 2: (E)-3-(3-acetyl-4-hydroxyphenoxy)propyl-3-(4-acetoxy-3-methoxyphenyl)acrylate
[0085]
[0086] In step 1 of this example, the paeonol in step 1 of example 1 is replaced with equimolar 2,4-dihydroxyacetophenone (compound I-2), and the other steps are the same as step 1 of example 1 to obtain 3.52 g White crystal compound III-2, yield 85%. In step 3 of this example, compound III-1 in step 3 of example 1 was replaced with equimolar compound III-2, and the other steps were the same as step 3 of example 1 to obtain 4.71 g of white solid compound VI-2, namely compound 2. The yield is 65%, m.p.143~144℃, and the structural characterization data are: 1 H NMR (400MHz, CDCl 3 )δ: 12.74(s,1H),7.66(s,1H),7.64(d,J=1.2Hz,1H),7.63(t,1H),7.17(s,1H),7.13(d,J=1.9 Hz,1H),7.10(dd,J=3.8,1.8Hz,2H),7.06(s,1H),7.04(s,1H),6.45(d,J=2.5Hz,1H),6.44-6.42(m ,2H),6.40(s,1H),6.36(s,1H),4.40(t,J=6.2Hz,2H),4.14(t,J=6.1Hz,2H),3.88(s,6H),2.55 (s,3H),2.23(s,3H)2.19-2.16(m,2H...
Embodiment 3
[0088] Synthesis of compound 3: (E)-3-(4-allyl-2-methoxyphenoxy)propyl-3-(4-acetoxy-3-methoxyphenyl)acrylate
[0089]
[0090] In step 1 of this example, equimolar eugenol (compound I-3) was used to replace paeonol in step 1 of example 1, and the other steps were the same as step 1 of example 1 to obtain 2.58g of white crystal compound III-3 , yield 88%. In step 3 of this example, compound III-1 in step 3 of example 1 was replaced with equimolar compound III-3, and other steps were the same as step 3 of example 1 to obtain 3.78g of white crystal compound VI-3, namely compound 3. The yield is 68%, m.p.79~80℃, and the structural characterization data are: 1 H NMR (400MHz, CDCl 3 )δ: 7.64(d, J=16.0Hz, 1H), 7.26(s, 1H), 7.10(s, 2H), 7.05(d, J=8.0Hz, 1H), 6.84(d, J=8.7Hz, 1H), 6.71(d, J=6.1Hz, 1H), 6.38(d, J=16.0Hz, 1H), 5.95(d, J=16.8, 6.7Hz, 1H), 5.08(d, J=17.0Hz, 2H), 4.42(t, J=5.1Hz, 2H), 4.14(t, J=6.3Hz, 2H), 3.86(d, J=7.8Hz, 3H), 3.33(d, J=6.7Hz, 1H) ,2.24(dd,J=8.1,4....
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