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Aromatic thiazole compounds, analogues thereof, uses thereof and preparation methods thereof

A technology based on thiazoles and organic compounds, which is applied in the field of preparation of aryl thiazoles and their analogs, can solve problems that have not been reported in relevant literature, and achieve remarkable effects

Active Publication Date: 2015-02-18
BIORAY LABORATORIES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Arylthiazole compounds and their analogs have various biological activities, such as antitumor effect, antibacterial effect, kinase inhibitor, etc., but there is no relevant literature report about the anti-ultraviolet radiation effect of this type of compound, and the research of the present invention shows that This type of compound has a very good ability to absorb mid-band ultraviolet rays, and has a very significant protective effect on photodamage, and has a wide range of applications in the development of new sunscreens and anti-ultraviolet products

Method used

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  • Aromatic thiazole compounds, analogues thereof, uses thereof and preparation methods thereof
  • Aromatic thiazole compounds, analogues thereof, uses thereof and preparation methods thereof
  • Aromatic thiazole compounds, analogues thereof, uses thereof and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0113] Example 1-1, 2-(2-ethyl-4-pyridyl)-4-methylthiazole-5-carboxylic acid ethyl ester (KZW001)

[0114] Dissolve the compound 2-ethylpyridyl 4-sulfuramide (332mg, 2.0mmol) in absolute ethanol (5ml), add ethyl bromoacetoacetate (627mg, 3.0mmol) to the reaction system under a nitrogen atmosphere Heat to reflux, stop the reaction after TLC detects that there is no raw material, cool to room temperature, remove the solvent under reduced pressure, and obtain compound 2-(2-ethyl-4-pyridyl)-4-methylthiazole after purification by column chromatography -Ethyl 5-carboxylate (475 mg, 86%): 1 H NMR (300MHz, CDCl 3 ): 8.63(d, J=5.1Hz, 1H), 7.70(s, 1H), 7.60(d, J=5.1Hz, 1H), 4.37(q, J=7.2Hz, 2H), 2.91(q, J =7.5Hz, 2H), 2.80(s, 3H), 1.40(t, J=7.2Hz, 3H), 1.36(t, J=7.5Hz, 3H).

Embodiment 1-2 to 1-35

[0115] Preparation of KZW002-45 carboline compounds shown in Examples 1-2 to 1-35 and Table 1 (see reference below for specific process)

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] Table 1

Embodiment 2

[0122] Example 2: The protective effect of a certain dose of the compound of the present invention on the skin under ultraviolet irradiation and the inhibition of apoptosis and the increase of COX2 expression

[0123] 2-1. Cell culture

[0124] Human normal skin HaCaT cells used in this experiment were purchased from the Shanghai Cell Bank of the Chinese Academy of Sciences, and cultured in a 37°C constant temperature incubator (humidity 95%, CO 2 5%), cultured in RPMI-1640 medium containing 100U / mL penicillin, 100μg / mL streptomycin and 10% calf serum, changing the medium every day, and passaged once every 2-3 days. Inoculated in 90mm Petri dishes.

[0125] 2-2, the protective effect of the compound of the present invention on ultraviolet UVB radiation HaCaT cells

[0126] Human skin keratinocytes HaCaT were treated with 1 × 10 5 The cell density of cells / ml was placed in a 96-well plate. After 12 hours of conventional culture, the compound of the present invention was adde...

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Abstract

The invention discloses aromatic thiazole micro-molecular organic compounds with the structural formula represented by formula (I), or hydrates thereof or pharmaceutically acceptable salts thereof. The compounds of the invention or compositions containing the compounds can be used for sun protection, anti-ultraviolet and skin damage protection as a cosmetic additive and for inhibition of the cell apoptosis caused by excess ultraviolet irradiation and the expression of cyclooxygenase COX2. The invention also discloses preparation methods of the aromatic thiazole micro-molecular organic compounds and derivatives thereof.

Description

technical field [0001] The present invention relates to a class of arylthiazole compounds and their analogs, and the compounds or compositions containing the compounds can be used as cosmetic additives in sunscreen and anti-ultraviolet products and for the protection of skin damage, and can also be used It is used to inhibit the apoptosis induced by excessive ultraviolet irradiation and the expression of cyclooxygenase COX2. The invention also relates to the preparation method of the aryl thiazole compound and its analogs. Background technique [0002] The skin is directly irradiated by ultraviolet rays from the sun, and excessive exposure will damage cellular tissues such as DNA, fat membrane, and mitochondria, thereby causing skin aging, apoptosis of related cells, and even canceration. Studies have shown that after ultraviolet radiation can induce a variety of skin damage, including photoaging, wrinkles, sunburn, cataract, visual damage, immune damage, various skin cance...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14C07D277/56C07D333/38C07D307/68C07D263/34A61K8/49A61K31/4439A61K31/4545A61K31/426A61K31/381A61K31/341A61K31/421A61Q17/04A61P17/16A61P35/00A61P29/00
Inventor 陈益华叶希韵刘明耀李国亮何云东周文波
Owner BIORAY LABORATORIES INC
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