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Ester derivative of high veratryl alcohol and medical treatment application

A technology of ester derivatives and homoveratrol, which is applied in the field of medicine, can solve the problems of affecting the therapeutic effect and fast biological metabolism, and achieve the effects of reducing the number of doses, slowing down the metabolic rate, and prolonging the drug action time

Inactive Publication Date: 2012-09-19
栗艳艳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a kind of ester derivative of homoveratrol and its therapeutic application, which can solve the problem of homoveratrol itself being easily hydrolyzed in living organisms and fast in biological metabolism. 1 / 2 Issues such as short-term impact on treatment effect

Method used

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  • Ester derivative of high veratryl alcohol and medical treatment application
  • Ester derivative of high veratryl alcohol and medical treatment application
  • Ester derivative of high veratryl alcohol and medical treatment application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1. Synthesis of Hoveratrol Cinnamon Ester

[0043] 1.1 Synthesis of Cinnamoyl Chloride

[0044] Add 3g (20.24mmol) cinnamic acid into a three-necked flask with a stirring device, add 10ml of dichloromethane, 5-7 drops of N,N-dimethylformamide, stir at room temperature and dropwise add 10ml of SOCl 2 . Stir at room temperature for 2 h, remove SOCl by suction filtration 2 , to obtain a colorless liquid, which was left to cool to obtain 3.2 g of a white solid, with a yield of 94.0%.

[0045] 1.2 Synthesis of homoveratrol cinnamon ester

[0046] Take 1.05g (6.24mmol) of cinnamonyl chloride from the previous reaction and add it to a three-necked flask with a stirring device, and then add 20ml of dry acetone, 20ml of dry Py, and 0.05g of DMAP under stirring at room temperature. After stirring evenly, add 0.39g of homoveratrol (1.73mmol) and 10ml of acetone mixture dropwise. After the dropwise addition, continue to react for 5h, filter, and the filtrate is rotary evaporate...

Embodiment 2

[0048] 2. Synthesis of homoveratrol nicotinate

[0049] 2.1 Synthesis of Nicotinyl Chloride

[0050] Add 3g (24.37mmol) of nicotinic acid into a three-necked flask with a stirring device, add 5-7 drops of N,N-'-methylformamide, 20mL of dichloromethane, stir at room temperature and dropwise add 10mL of SOCl 2 With 20mL dichloromethane mixture. After the dropwise addition, heat to 77°C and reflux for 2h, then remove SOCl by suction filtration 2 , and then add 20 mL of diethyl ether to reflux for 1 h, recover diethyl ether to obtain 4.2 g of white solid, yield 96.2%.

[0051] 2.2 Synthesis of homoveratrol nicotinate

[0052] Take the nicotinyl chloride reacted in the previous step and put it into a three-necked flask with a stirring device, and add 20Ml of dry pyridine under stirring at room temperature. After 5 minutes, add 0.71g (3.12mmol) homoveratrol and 10ml pyridine mixture dropwise. After the dropwise addition, raise the temperature to 75°C, stir for 3h, and recover py...

Embodiment 3

[0054] 3. Synthesis of glycyl homoveratrol

[0055] Add 3g of F-moc glycine and 20ml of oxalyl chloride into a 50ml round bottom flask, heat to 60°C and stir for 3h, remove unreacted oxalyl chloride by rotary evaporation under reduced pressure to obtain a white solid. Add 0.76g homoveratrol, 0.1g DMAP and 20ml pyridine into a 100ml three-necked flask equipped with a stirring device, add 20ml of toluene and the F-moc glycyl chloride mixed solution from the previous step dropwise at room temperature, and heat to 55°C for 6h. Add 20ml of water, extract 3 times with 100ml of ethyl acetate, combine the organic phases, add anhydrous Na 2 SO 4 Let dry overnight. The organic solvent was recovered under reduced pressure to obtain a yellow oily liquid. After separation by silica gel column, 0.61 g of white solid was obtained with a yield of 45%.

[0056] The compounds of Examples 1 and 2 have shown efficacy in xylene-induced mouse ear swelling and 10% egg white-induced rat paw swell...

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Abstract

The invention discloses an ester derivative of high veratryl alcohol and medical treatment application, and belongs to the field of medicines. A compound with biological activity is a compound in a general formula (I) shown in the specification, and salt, a solvate or a hydrate of the compound, wherein X1 is H or COR1, X2 is H or COR2, X3 is H or COR3, but X1, X2 and X3 are not H and 3-pyridyl simultaneously; R1, R2 and R3 are the same as one another or different from one another and are C1-C6 alkyl substituted by R4 or can be substituted by R9 at random and can contain one or more 4-7-membered rings of additional heteroatom of O, S(O)n and NR9; R4 is F, CF3, OR5, NR6R7 or S(O)nR8; R5, R6 and R7 are the same as one another or different from one another and are H or C1-C6 alkyl substituted by R4 at random, or NR6R7 is one or more C4-C6 heterocycle alkyl rings of the heteroatom of O, NR9 and S(O)n; each n is 0 to 2; R8 is C1-C6 alkyl; R9 is C1-C4 alkyl which is defined by R4 or substituted by R4 or halogens at random; and R9 is H or C1-C6 alkyl. The ester derivative has the effect of treating liver diseases, T-cell proliferation related diseases or proinflammatory cytokine mediated diseases.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to ester derivatives of homoveratrol and their therapeutic use. technical background [0002] Coratrol is an isomer of resveratrol, it has two configurations of cis and trans, the latter is the stable structure of colatrol, and its biological activity is more extensive. Its structural formula is: [0003] [0004] Studies have found that colatrol has the same pharmacological activity as resveratrol. These compounds were originally discovered as Phytoalxeni, an anti-stress substance of plants of the genus Vitis, and were subsequently discovered in various plants. Such as medicinal plants Cassia, Lilu, Polygonum cuspidatum, etc., and some are even food, such as grapes and peanuts. The content of these substances in grapes varies with different varieties. Since the discovery of colatrol and resveratrol, people have conducted in-depth research on their pharmacological activities. The two m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/618C07C67/14C07C269/06C07C271/22C07D213/80C07D213/803A61K31/455A61K31/27A61K31/216A61P1/16A61P29/00
Inventor 栗艳艳栗进飞栗飞
Owner 栗艳艳
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