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【结 构 式】 
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【药物名称】SH-3/24 【化学名称】cis-N-[3-[3,5-Dimethyl-4-(3-phenylpropyl)piperazin-1-yl]propyl]-N,N-diphenylamine hydrochloride 【CA登记号】 【 分 子 式 】C30H40ClN3 【 分 子 量 】478.1264 |
【开发单位】National Institute on Drug Abuse (Originator), National Institutes of Health (Originator), University of Oklahoma Health Sci. Cent. (Originator) 【药理作用】Treatment of Cocaine Dependency, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, Drugs Acting on Dopaminergic Transmission, sigma-Receptor Ligands |
合成路线1
Alkylation of diphenylamine (I) with THP-protected 3-bromopropanol (II) using NaH in 15-crown-5 yields tertiary amine (III), which is then deprotected with HOAc/H2O to provide (IV). Alcohol (IV) is treated with PPh3 and CBr4 to afford alkyl bromide (V), which is then converted into amine (VII) by reaction with 2,6-dimethylpiperazine (VI) in DMF/H2O in the presence of K2CO3. Finally, (VII) is acylated with 3-phenylpropionyl chloride (VIII) and reduced with LAH.
| 【1】 Vilner, B.J.; Husbands, S.M.; Bowen, W.D.; Newman, A.H.; Kopajtic, T.; Izenwasser, S.; Katz, J.L.; Structure-activity relationships at the monoamine transporters and sigma receptors for a novel series of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)-propyl]carbazole (rimcazole) analogues. J Med Chem 1999, 42, 21, 4446. |
| 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) | 42251 | Diphenylamine; N-phenylaniline; N,N-diphenylamine | 122-39-4 | C12H11N | 详情 | 详情 |
| (II) | 42252 | 3-bromopropyl tetrahydro-2H-pyran-2-yl ether; 2-(3-bromopropoxy)tetrahydro-2H-pyran | C8H15BrO2 | 详情 | 详情 | |
| (III) | 42253 | N-phenyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]aniline; N,N-diphenyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]amine | C20H25NO2 | 详情 | 详情 | |
| (IV) | 42254 | 3-(diphenylamino)-1-propanol | C15H17NO | 详情 | 详情 | |
| (V) | 42255 | N-(3-bromopropyl)-N-phenylaniline; N-(3-bromopropyl)-N,N-diphenylamine | C15H16BrN | 详情 | 详情 | |
| (VI) | 20848 | (2R,6S)-2,6-dimethylpiperazine | C6H14N2 | 详情 | 详情 | |
| (VII) | 42256 | N-[3-[(3R,5S)-3,5-dimethylpiperazinyl]propyl]-N,N-diphenylamine; N-[3-[(3R,5S)-3,5-dimethylpiperazinyl]propyl]-N-phenylaniline | C21H29N3 | 详情 | 详情 | |
| (VIII) | 16240 | 3-phenylpropanoyl chloride; Hydrocinnamoylchloride | 645-45-4 | C9H9ClO | 详情 | 详情 |