【结 构 式】 |
【药物名称】TU-753 【化学名称】17-(2-Methyl-2-propenyl)-4,5alpha-epoxy-3,14-dihydroxy-6,7-didehydroindolo[2',3':6,7]morphinan 【CA登记号】 【 分 子 式 】C26H26N2O3 【 分 子 量 】414.50872 |
【开发单位】National Institute on Drug Abuse (Originator), National Institutes of Health (Originator), University of Arizona (Originator) 【药理作用】Treatment of Cocaine Dependency, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, delta-Opioid Antagonists |
合成路线1
Noroxymorphindole (III) was prepared by Fischer indole synthesis from noroxymorphone (I) and phenylhydrazine (II) under acidic conditions. Alkylation of (III) with 2-methyl-2-propenyl bromide (IV) in the presence of NaHCO3 in DMF afforded the title compound.
【1】 McLamore, S.; et al.; Effect of N-alkyl and N-alkenyl substituents in noroxymorphindole, 17-substituted-6,7-dehydro-4,5alpha-epoxy-3,14-dihydroxy-6,7:2',3'-indolomorphinans on opioid receptor affinity, selectivity, and efficacy. J Med Chem 2001, 44, 9, 1471. |
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) | 33927 | (1S,5R,13R,17S)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one | C16H17NO4 | 详情 | 详情 | |
(II) | 11818 | Phenyl hydrazine; 1-Phenylhydrazine | 100-63-0 | C6H8N2 | 详情 | 详情 |
(III) | 50974 | (1S,2S,13R,21R)-14-oxa-11,22-diazaheptacyclo[13.9.1.0(1,13).0(2,21).0(4,12).0(5,10).0(19,25)]pentacosa-4(12),5,7,9,15(25),16,18-heptaene-2,16-diol | C22H20N2O3 | 详情 | 详情 | |
(IV) | 40015 | 3-bromo-2-methyl-1-propene | 1458-98-6 | C4H7Br | 详情 | 详情 |