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Coumarone compound, its preparation method and its application

A kind of technology of benzofuran and compound is applied in the field of benzofuran compound and its preparation and use, and can solve the problems such as less research on PPAR agonist

Inactive Publication Date: 2014-06-18
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the research on the anti-tumor effect of PPAR agonists has been carried out for a period of time, the current research focus of medicinal chemists is to use known anti-diabetic drugs mainly thiazolidinediones as templates to study their anti-tumor mechanism. There are relatively few studies on new PPAR agonists with anti-tumor effects

Method used

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  • Coumarone compound, its preparation method and its application
  • Coumarone compound, its preparation method and its application
  • Coumarone compound, its preparation method and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Synthesis of 4-(benzyloxy)-2-hydroxybenzaldehyde I ( figure 1 ): Dissolve 2,4-dihydroxybenzaldehyde (100mg, 0.72 mmol) in acetonitrile (15ml), then add potassium iodide (179.3mg, 1.08mmol) and sodium bicarbonate (90.7 mg, 1.08mmol), after adding , slowly dropwise added benzyl chloride (100 ul, 0.87mmol), and refluxed for 12 hours. After the reaction was completed, it was quenched with water, extracted with ethyl acetate, combined organic phases, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, purified by silica gel chromatography (petroleum ether: ethyl acetate=10 : 1) Obtain 110 mg of 4-(benzyloxy)-2-hydroxybenzaldehyde (colorless solid, yield 67%). 1 HNMR (CDCl 3 ;300MHz), δ5.12(s, 2H, O CH 2 Ph) 6.40-6.64(m, 2H, ArH), 7.41-7.43 (m, 6H, ArH), 9.73(s, 1H, CHO), 11.44(brs, 1H, OH).

Embodiment 2

[0042] (E)-5-(Benzyloxy)-2-(4-methoxystyryl)phenol II 1 Synthesis( figure 1 ): Under nitrogen atmosphere, add zinc powder (1.4g, 22mmol) into anhydrous tetrahydrofuran (20ml), then lower the temperature of the reaction system to -5~0°C, and add titanium tetrachloride dropwise at this temperature (1.2ml, 11mmol), after the addition, the temperature of the reaction system was raised to room temperature, stirred for half an hour, and then refluxed for 2.5 hours. After the reflux, the temperature of the reaction system was lowered to -5~0°C again, and 4-(benzyloxy)-2-hydroxybenzaldehyde (1g, 4.4mmol) and p-methoxybenzaldehyde (721mg, 5.3mmol) of tetrahydrofuran solution, refluxed for 2 hours after dropping. After the reaction was completed, the reaction was quenched with 10% aqueous sodium bicarbonate solution, then extracted with dichloromethane, the organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated under re...

Embodiment 3

[0044] 6-(Benzyloxy)-2-methoxybenzofuran III 1 Synthesis( figure 1 ): Dissolve (E)-5-(benzyloxy-2-(4-methoxystyryl)phenol (280mg, 0.84mmol) in tetrahydrofuran (15ml), add anhydrous potassium carbonate (695 mg, 5.04mmol), stirred for 10 minutes, added iodine (1.28g, 5.04mmol), and stirred at room temperature for 12 hours. After the reaction ended, quench the reaction with saturated aqueous sodium bicarbonate solution, then add dropwise saturated aqueous sodium bisulfite solution to remove Remove residual iodine, then extract with ethyl acetate, combine the organic phases, wash three times with saturated brine, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and purify through silica gel chromatography (petroleum ether:ethyl acetate=5:1 ), to obtain 150 mg of 6-(benzyloxy)-2-methoxybenzofuran (yellow solid, yield 54%). 1 HNMR (CDCl 3 ;300MHz), δ3.87(s, 3H, OCH 3 ), 5.14(s, 2H, O CH 2 Ph), 6.826(s, 1H, ArH), 6.889-6.918(d, 1H, ArH, J=8.7Hz), 6.968-6....

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Abstract

The invention provides a coumarone compound, a preparation method and an application in the medical and chemical field, the structural formula of the coumarone compound is shown as a following formula. The invention also relates to the preparation method of the compound and the application of the compound in preparation of medicines used for inhibiting tumor cells biological activity. According to the invention, a traditional PPAR agonist hydrophobic tail hydrophobic tail and a flexible intermediate coupling chain are taken as a mother nucleus, a cis-structure of CombretastinA-4 is referred so that the good antineoplastic activity is presented, the coumarone structure is taken as an aromatic ring center between an acidic head and the flexible coupling chain in the PPAR agonist, the preparation method of compound is established and optimized, and the prepared novel compound is carried out an experiment for screening the tumor cells. The preliminary antineoplastic tests confirm that the prepared partial novel compound has specific and exclusive tumor inhibition activity aimed at human prostatic cancer cells, the coumarone compound can be used for preparing the antitumor medicines and medicines for treating and preventing tumor.

Description

technical field [0001] The present invention relates to a compound in the field of medicine and chemical industry and its preparation method and use, specifically a [0002] Benzofuran compounds and their preparation methods and uses. Background technique [0003] Peroxisome Proliferator-Activated Receptors (PPARS) is a superfamily of nuclear hormone receptors, including three subtypes of PPARα, PPARβ and PPARγ, which were first discovered in Xenopus . PPARS is a class of ligand-dependent transcription factors that can regulate the expression of target genes related to fat and glucose metabolism. Each PPAR receptor can form a complex with the retinoic acid X receptor, and this complex can bind to a specific peroxisome proliferator response factor (PPRE) to recognize the DNA sequence of the target gene. From the discovery of PPARs in the 1990s to the present, PPARS receptors are regarded as potential targets for the treatment and prevention of metabolic syndrome. Medicinal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C07D413/12A61K31/422A61P35/00A61P35/02
Inventor 傅磊刘井宝姜发琴蒋玺臻刘晶晶刘文陆
Owner SHANGHAI JIAO TONG UNIV
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