3-(4-METHYL-2-THIAZOLYL)-6-PROPYL-7-(1-METHYL-1-ETHOXYCARBONYL)-METHOXYCHROMONE SHOWING HYPOGLYCEMIC, HYPOLIPIDEMIC AND ANALEPTIC EFFECT

摘要

FIELD: organic chemistry. SUBSTANCE: product: 3-(4-methyl-2-thiazolyl)-6-propyl-7-(1-methyl-1-ethoxycarbonyl)-methoxychromone (I), empirical formula is C₂₁H₂₃NO₅S, m. p. is 103-104 C. Reagent 1: 4-methyl-2-cyanomethylthiazole bromohydrate. Reagent 2: 4-propylresorcinol. Reaction conditions: in the presence of boron trifluoride etherate in dry HCl flow. Reagent 3: (4-methyl-2-thiazolyl)-2,4-dihydroxy-5-propylacetophenone. Reagent 4: acetoformate anhydride. Reaction conditions: at 80-100 C. Reagent 5: 3-(4-methyl-2-thiazolyl)-6-propyl-7-hydroxychromone. Reagent 6: -bromopropionic acid ethyl ether. Process conditions: in the presence of potash, in medium of absolute acetone. Value LD₅₀ is 6100 mg/kg (at intragastral administration). Average sugar content decrease in blood for 10 hr at dose of (I) 50 mg/kg is 47% and this index exceeds that for butamide by 32%. At dose 100 mg/100 g living body mass this substance decreases cholesterol and triglyceride level by 44.2 and 49.6%, respectively. Barbiturate sleep duration is decreased up to 51.8 2.1 min. at dose 100 mg/kg. Synthesized compound is used in medicine. EFFECT: improved method of synthesis.