Vitamin A compound and paeonol condensed derivatives and preparation method

A technology of paeonol and derivatives is applied in the field of derivatives and preparations of the condensation of vitamin A compounds and paeonol, and can solve the problems of reducing skin and mucous membrane irritation of vitamin A compounds, so as to promote epithelial cell differentiation, lipid Increased solubility and reduced irritation

Inactive Publication Date: 2017-05-10
苏州药基美研医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sometimes irritation is more pronounced, causing users to forego retinoids
"Blocking" these groups in...

Method used

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  • Vitamin A compound and paeonol condensed derivatives and preparation method
  • Vitamin A compound and paeonol condensed derivatives and preparation method
  • Vitamin A compound and paeonol condensed derivatives and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] One-step method, using one-step method to synthesize compound I((2E,4E,6E,8E)-2-acetyl-5-methoxyphenyl3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl )nona-2,4,6,8-tetraenoate).

[0049] In a 250mL round-bottom flask, add 100mL of dry dichloromethane, 10.0g of tretinoin, 5.56g of paeonol, 6.87g of DCC and 0.21g of DMAP, and stir for 24h under nitrogen at room temperature and protected from light;

[0050] The solid was removed by filtration, the filtrate was concentrated, and the obtained oily product was purified by silica gel column chromatography, and the column chromatography eluent was hexane-ethyl acetate (100:1 to 5:1);

[0051] The corresponding effluent was collected and concentrated and dried with a rotary evaporator to obtain a yellow solid. LCMS: 449.4 (M+1). mp: 101-102°C. H NMR (Brucker AV-300, CDCl3, δppm): 1.04 (s, 6H), 1.46-1.49 (m, 2H), 1.59-1.64 (m, 2H), 1.73 (s, 3H), 2.03 (brs, 5H) ),2.40(s,3H),2.52(s,3H), 3.83(s,3H), 6.02(s,1H), 6.15–6.41(m,4H),6.91(...

Embodiment 2

[0054] Synthesis of compound I using a two-step method

[0055] ((2E,4E,6E,8E)-2-acetyl-5-methoxyphenyl3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6, 8-tetraenoate).

[0056] In a 250mL round bottom flask, add 70mL of dry dichloromethane and 10.0g of tretinoin;

[0057] Cool with ice water to an internal temperature of 5°C, slowly add 4.2 g of oxalyl chloride dropwise, and stir in an ice water bath for 2 hours after the addition is complete;

[0058] 5.56g of paeonol and 6.72g of triethylamine were dissolved in 50mL of dry dichloromethane and slowly added dropwise;

[0059] After the addition is complete, remove the ice-water bath, stir at room temperature for 2 hours, add 50 mL of water, and separate;

[0060] Wash the organic phase three times with 50mL each time;

[0061] Na for organic phase 2 SO 4 After drying and concentration, the obtained oily product was purified by silica gel column chromatography. The column chromatography eluent is hexane-ethyl acetate (100:1 ...

Embodiment 3

[0065] The configuration of vitamin A compound solution. Compound I (10.0g) was dissolved in isosorbide dimethyl ether (90.0g) to obtain a 10% solution, which should be stored away from light.

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Abstract

The invention discloses vitamin A compound and paeonol condensed derivatives and a preparation method. The vitamin A compound and paeonol condensed derivatives include derivatives in structures I-VII shown as follows; a structure I is ester formed by paeonol and all-trans retinoic acid; a structure II is ester formed by paeonol and 13-cis-retinoic acid; a structure III is ester formed by paeonol and acitretin; a structure IV is ester formed by paeonol and 9-cis-retinoic acid; a structure V is ester formed by paeonol and adapalene; a structure VI is ester formed by paeonol and tazarotene; a structure VII is ester formed by paeonol and bexarotene. By the vitamin A compound and paeonol condensed derivatives and the preparation method, irritation of vitamin A compounds to skin mucosa is relieved; after application to skin, the vitamin A compounds and paeonol are released under the action of hydrolase to dissolve cutin, promote epithelial cell differentiation and the like so as to realize anti-inflammatory and anti-oxidation functions.

Description

Technical field [0001] The invention relates to the field of physiologically active substances, in particular to a derivative of a vitamin A compound condensed with paeonol and a preparation method. Background technique [0002] Vitamin A is involved in the biosynthesis of rhodopsin, embryo formation, cell growth and differentiation. Retinol and retinol fatty acid esters are converted into each other in the body, and retinol fatty acid esters are the main storage form. Retinol is oxidized to retinal, which continues to be oxidized to retinoic acid. Retinoic acid is considered to be the active form of vitamin A, which binds to nuclear receptors and regulates gene expression. The natural vitamin A compounds currently used are mainly retinol, retinol fatty acid esters, retinal, retinoic acid, retinoic acid derivatives, retinoic acid isomers (aliretinoic acid, isovitamin A acid). These compounds belong to the first generation of vitamin A substances. The representative of the se...

Claims

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Application Information

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IPC IPC(8): C07C403/20C07D409/06C07C69/773C07C69/734C07C67/08A61P17/10A61P17/08A61P17/12A61P17/06A61P17/16A61P17/18A61P17/00
CPCC07C67/08C07C69/734C07C69/76C07C403/20C07D409/06
Inventor 李维宽杜雪琴
Owner 苏州药基美研医药科技有限公司
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