DECURSIN AND SYNTHESIS METHOD THEREOF

• Main Authors: AHN, GYEONG SEOP, KIM, HYEON HO, JUNG, SE YEONG, KIM, IK HWAN, LIM, JONG DU, HAN, HO GYU
• Format: Patent
• Language: English; Korean
• Published: 16.01.2002
• Edition: 7
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

PURPOSE: Provided is decursin and its synthesis method, which decursin has strong lethal effects on cancer cells, but less lethal effects on normal cells. Decursin is manufactured by using decursinol which is its precursor. Therefore, anticancer agents containing decursin as an effective ingredient are mass-produced in high yields. CONSTITUTION: The manufacturing method of decursin comprises the steps of: adding methane sulfonic acid to P4O10 to prepare 7-hydroxy-2,2-dimethylcroman-4-on of the formula(1); adding LiAlH4 to tetrahydrofuran then adding the compound of the formula(1) thereto to obtain 2,2-dimethyl croman-4,7-diol of the formula(2); adding p-toluene sulfonic acid and THF to the compound of the formula(2) to prepare 2,2-dimethyl-2H-chromen-7-ol of the formula(3); adding the compound for he formula(3), acetic anhydride, pyridine and 4-dimethyl amino pyridine to methylene chloride to obtain 7-acetoxy-2,2-dimethyl-2H-chromen of the formula(4); adding the compound of the formula(4), na2B4O7·10H2O, n-bu4NHSO4 and 1,1,1-trifluoroaceton to CH2CN, then adding NaHCO3 solution and oxone solution to obtain 7-acetoxy-3,4-epoxy-2,2-dimethylcroman of the formula(5); adding LiAlH4 and THF to the compound of the formula(5) to prepare 2,2-dimethylcroman-3,7-diol of the formula 96); adding ZnCl2, ethylpropyolate and HCl solution to prepare decursinol of the formula(7); and adding 3,3-dimethylacryloyl chloride, the compound of the formula(7) and pyridine to obtain decursin.