Coumarin derivative, preparation method of coumarin derivative and purpose of coumarin derivative as medicine
A compound, unsubstituted technology, applied in the field of GPR40 agonist, preparation of drugs for prevention or treatment of diabetes and related diseases, and metabolic syndrome, which can solve problems such as hypoglycemia and weight gain, side effects of edema, and side effects
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Embodiment 1
[0113] 2-(7-(Benzyloxy-4-methyl-2-oxo-2H-chroman-3-)acetic acid (I-1)
[0114]
[0115] Compound IV (200mg, 0.76mmol) was dissolved in 10mL of acetone, followed by adding K 2 CO 3 (211mg, 1.52mmol), a catalytic amount of KI and compound V-1 (130mg, 0.76mmol), heated and refluxed overnight, after the reaction, filtered, and concentrated the filtrate under reduced pressure. The residue was separated by silica gel column chromatography (eluent system: petroleum ether and ethyl acetate) to obtain the target product VI-1 (220 mg, white solid), yield: 81.8%.
[0116] Compound VI-1 (200mg, 0.57mmol) was dissolved in 6mL tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 2M sodium hydroxide solution (0.57mL, 1.14mmol) was added, and the reaction was stirred at room temperature for 2h , after the reaction, add 10mL of water, add dropwise 1M hydrochloric acid until the pH of the reaction solution is 3, extract with ethyl acetate (30mL×3), combine the organic phase...
Embodiment 2
[0122] 2-(4-Methyl-7-((2-methylbenzyl)oxy)-2-oxo-2H-chroman-3-)acetic acid (I-2)
[0123]
[0124] Compound IV (200mg, 0.76mmol) was dissolved in 10mL of acetone, followed by adding K 2 CO 3 (211mg, 1.52mmol), a catalytic amount of KI and compound V-2 (140mg, 0.76mmol), heated and refluxed overnight, after the reaction, filtered, and concentrated the filtrate under reduced pressure. The residue was separated by silica gel column chromatography (eluent system: petroleum ether and ethyl acetate) to obtain the target product VI-2 (213 mg, white solid), yield: 76.2%.
[0125] Compound VI-2 (200mg, 0.55mmol) was dissolved in 6mL tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 2M sodium hydroxide solution (0.55mL, 1.09mmol) was added, and the reaction was stirred at room temperature for 2h , after the reaction, add 10mL of water, add dropwise 1M hydrochloric acid until the pH of the reaction solution is 3, extract with ethyl acetate (30mL×3), combine the or...
Embodiment 3
[0131] 2-(4-Methyl-7-((3-methylbenzyl)oxy)-2-oxo-2H-chroman-3-)acetic acid (I-3)
[0132]
[0133] Compound IV (200mg, 0.76mmol) was dissolved in 10mL of acetone, followed by adding K 2 CO 3 (211mg, 1.52mmol), catalytic amount of KI and compound V-3 (141mg, 0.76mmol), heated to reflux for overnight reaction, after the reaction was completed, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography (eluent system: petroleum ether and ethyl acetate) to obtain the target product VI-3 (242 mg, white solid), yield: 86.6%.
[0134] Compound VI-3 (200 mg, 0.55 mmol) was dissolved in 6 mL of tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 2M sodium hydroxide solution (0.55 mL, 1.09 mmol) was added, and the reaction was stirred at room temperature for 2 h , after the reaction, add 10mL of water, add dropwise 1M hydrochloric acid until the pH of the reaction solution is 3, extract with eth...
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