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Cajanonic acid A structural analog, composition thereof and application thereof in medicines
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A drug and compound technology, applied in the field of stearic acid A structural analogs and compositions thereof, can solve the problems of poor patient compliance and the like
Inactive Publication Date: 2019-12-13
GUIZHOU MEDICAL UNIV
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Problems solved by technology
However, at present, stickyronic acid A is mainly administered by injection, and patients have poor compliance with injection administration.
Method used
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Embodiment 1
[0064] Example 1: Ethyl 2,4-dihydroxy-6-methylbenzoate
[0065]
[0066] Under nitrogen protection, 60% sodium hydride (8.00 g, 0.20 mol) was suspended in anhydrous THF (200 mL), and ethyl acetoacetate (26.00 g, 0.20 mol) was slowly added dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 h. The reaction solution was cooled to -78°C, and 2.5 mol / L n-butyllithium (80 mL, 0.20 mol) was slowly added. Subsequently, the temperature was slowly raised to reflux for 12 h. Cool to room temperature, quench the reaction with 20% refrigerated 12mol / L hydrochloric acid, extract with ethyl acetate (200mL×3), concentrate under reduced pressure below 30°C to obtain a brown oil, add saturated sodium bicarbonate (150mL) and let stand for 1d to acidify , extracted with ethyl acetate (200mL×5), combined the organic phases, washed with saturated sodium chloride (200mL×3), washed with water (200mL×3), dried over anhydrous sodium sulfate, and concentrated under red...
[0069] Take ethyl 2,4-dihydroxy-6-methylbenzoate (8.50g, 0.04mol), dissolve it in dry acetone (120mL), add anhydrous potassium carbonate (23.91g, 0.17mol), methyl iodide ( 3.20mL, 0.05mol), react at room temperature for 10 hours, after the reaction is complete, the reaction solution is suction filtered, the filter cake is washed with acetone, and the filtrate is distilled at atmospheric pressure, and the distilled material is dissolved in ethyl acetate (100mL), and then water ( 100 mL×3), washed with saturated sodium chloride (100 mL×3), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a brown solid. with V (石油醚) :V (乙酸乙酯) =20:3 Column chromatography was carried out to obtain 6.47g of white solid with a yield of 71%.
Embodiment 3
[0070] Example 3: Ethyl 2-prenyloxy-4-methoxy-6-methylbenzoate
[0071]
[0072] Take ethyl 2-hydroxy-4-methoxy-6-methylbenzoate (6.47g, 0.03mol), dissolve it in DMF (30mL), add anhydrous potassium carbonate (16.98g, 0.12mol), isoamyl Alkenyl bromide (4.26mL, 0.03mol), react at room temperature for 2h, add water (100mL) after the reaction, extract with ethyl acetate (100mL×3), combine organic phases, wash with water (100mL×3), and saturated sodium chloride solution (100mL×3) washed, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and (石油醚) :V (乙酸乙酯) =30:1 Column chromatography was carried out to obtain 5.45 g of colorless oil, yield 63.6%.
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Abstract
The present invention is a divisional application with application number of 2016103161377 and application date of May 13, 2016, and the name is " Cajanonic acid A structural analog, composition thereof and application thereof in medicines ". The invention discloses a Cajanonic acid A structural analog as shown in formula (II), and stereoisomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites, esters, pharmaceutically acceptable salts or prodrugs thereof. The invention also discloses a pharmaceutical composition containing the Cajanonic acid A structural analogshown in the formula (II), stereoisomers, hydrates or pharmaceutically acceptable salts thereof, and the compound or the pharmaceutical composition is mainly used for protecting, treating, treating orreducing type 2 diabetes and complications of patients, reducing blood lipid, weight loss and the like.
Description
[0001] The application of the present invention is a divisional application with the application number 2016103161377, the application date was May 13, 2016, and the invention title is "Structural analogue of gariculonic acid A, its composition and its application in medicine". [0002] field of invention [0003] The present invention relates to a structure analogue of jacaronic acid A and a composition thereof, and also relates to the application of the compound in reducing blood sugar and lipid. [0004] Background of the invention [0005] Diabetes mellitus (DM) is a systemic chronic secretory and metabolic disease associated with genetic factors. It is a metabolic disorder of sugar, fat, and protein caused by absolute or relative insufficiency of insulin secretion in the body. Its main features are hyperglycemia and urine sugar, often accompanied by atherosclerotic cardiovascular and cerebrovascular diseases, diabetic nephropathy, nervous system lesions and eye lesions suc...
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