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.

Pending Publication Date: 2020-07-24
SHAANXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, according to the synthesis and activity studies of new tyrosinase inhibitors reported at home and abroad, on the one hand, some compounds with high activity lack cell experiments such as cytotoxicity, and their reliable safety cannot be confirmed; on the other hand, tyrosine Insufficient enzyme inhibitory activity

Method used

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  • Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels
  • Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels
  • Cinnamate derivatives and application of cinnamate derivatives as tyrosinase inhibitors and gels

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention discloses cinnamate derivatives and application of the cinnamate derivatives as tyrosinase inhibitors and gels, and the structural general formula of the cinnamate derivatives is shown in the specification, in the formula, X and Y independently represent any one of O, S and NH, wherein R1 and R2 independently represent any one of H, OH, methoxy, allyl and acetyl; R3 and R4 respectively and independently represent any one of H, OH, methoxy, tert-butyl dimethyl siloxy and carbethoxy, and R3 and R4 are not tert-butyl dimethyl silyl at the same time; and n is an integer from 2 to 5.The cinnamate derivatives disclosed by the invention have obvious inhibitory activity on the activity of mushroom tyrosinase diphenolic enzyme and the content of tyrosinase and melanin in melanoma cells of B16F10 mice, and can be used for preparing the tyrosinase inhibitors. Meanwhile, the cinnamate derivatives can form stable gels in olive oil and can be used as micromolecular gels for cosmeticsand the like.

Description

technical field [0001] The present invention relates to a class of cinnamate derivatives with activity of inhibiting tyrosinase. Background technique [0002] Tyrosinase is involved in the production of melanin and is a key enzyme that limits melanin production. Due to the abnormal activity of tyrosinase, a series of highly active quinones will be produced, leading to excessive pigmentation, which will affect the appearance of the skin, such as melasma, freckles, age spots, post-inflammatory melanosis and other melanosis, many research reports Excessive melanin deposition can even lead to melanoma and early onset Alzheimer's disease. In particular, melanoma is characterized by a high degree of malignancy and high mortality. According to statistics from Peking University Cancer Hospital in 2018, the detection rate of melanoma in my country is currently increasing rapidly, with 20,000 new cases every year. Tyrosinase plays a key role in the process of melanin production and ...

Claims

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Application Information

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IPC IPC(8): C07C69/734C07C69/73C07C69/618C07C67/08C07F7/18A61K8/04A61K8/37A61K8/58A61Q19/00A61P17/00A61P43/00
CPCC07C69/734C07C69/73C07C69/618C07F7/1804C07F7/1892A61K8/042A61K8/585A61K8/37A61Q19/00A61P17/00A61P43/00
Inventor 邓翀姜祎唐凯张化为黄文丽宋小妹王薇颜永刚
Owner SHAANXI UNIV OF CHINESE MEDICINE
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