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【结 构 式】 
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【药物名称】NO-Ursodeoxycholic acid, NO-UDCA, NCX-1000 【化学名称】(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-oic acid 2-methoxy-4-[3-[4-(nitrooxy)butoxy]-3-oxo-1(E)-propenyl]phenyl ester 【CA登记号】301828-26-2 【 分 子 式 】C38H55NO10 【 分 子 量 】685.86275 |
【开发单位】NicOx (Originator), Axcan (Licensee) 【药理作用】GASTROINTESTINAL DRUGS, Liver and Biliary Tract Disorders, Treatment of, Apoptosis Inhibitors, Caspase 3 Inhibitors, Caspase 8 Inhibitors, Caspase 9 Inhibitors, Cytokine Production Inhibitors, Nitric Oxide Donors |
合成路线1
Ferulic acid (I) was converted to the 4-bromobutyl ester (II) upon treatment with carbon tetrabromide, triphenylphosphine and THF also as the solvent. Coupling of dihydroxycholanoic acid (III) with ferulic acid bromobutyl ester (II) using DCC in the presence of DMAP furnished diester (IV). Finally, displacement of the bromide group of (IV) with silver nitrate gave rise to the title nitrooxy derivative.
| 【1】 Del Soldato, P. (NicOx SA); Pharmaceutical cpds.. WO 0061604 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 48091 | (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid | 1135-24-6 | C10H10O4 | 详情 | 详情 |
| (II) | 48092 | 4-bromobutyl (E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate | C14H17BrO4 | 详情 | 详情 | |
| (III) | 48093 | (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | 128-13-2 | C24H40O4 | 详情 | 详情 |
| (IV) | 48094 | 4-bromobutyl (E)-3-[4-([(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxy)-3-methoxyphenyl]-2-propenoate | C38H55BrO7 | 详情 | 详情 |