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【结 构 式】 
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【药物名称】 【化学名称】9-(3,3-Diphenyl-2-propenyl)-3-propionyl-3,9-diazabicyclo[3.3.1]nonane 【CA登记号】355004-85-2 (monoHCl) 【 分 子 式 】C25H30N2O 【 分 子 量 】374.53065 |
【开发单位】Cent Consortile Ric Neuropsicofarmacol (Originator), Università degli Studi di Cagliari (Originator), Università degli Studi di Milano (Originator), Università degli Studi di Sassari (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Opioid Analgesics, mu-Opioid Agonists |
合成路线1
Horner-Emmons condensation of benzophenone (I) with triethyl phosphonoacetate provides the unsaturated ester (II), which is further reduced with DIBAL in toluene to the allylic alcohol (III). Reaction of alcohol (III) with methanesulfonyl chloride and Et3N leads to chloride (IV). Finally, alkylation of 3-propionyl-3,9-diazabicyclo[3.3.1]nonane (V) with the allyl chloride (IV) furnishes the title compound.
| 【1】 Pinna, G.A.; Cignarella, G.; Loriga, G.; Murineddu, G.; Mussinu, J.-M.; Ruiu, S.; Fadda, P.; Fratta, W.; N-3(9)-Arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as mu-opioid receptor agonists. Effects on mu-affinity of arylalkenyl chain modifications. Bioorg Med Chem 2002, 10, 6, 1929. |
| 【2】 Cignarella, G.; Pinna, G.A. (Centro Consortile Ricerche Neuropsicofarmacologiche a.r.l); 3,9-Diazabicyclo[3.3.1]nonane derivs. with analgesic activity. EP 1259511; WO 0160823 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
| (I) | 18732 | benzophenone | 119-61-9 | C13H10O | 详情 | 详情 |
| (II) | 61015 | ethyl 3,3-diphenylacrylate | C17H16O2 | 详情 | 详情 | |
| (III) | 61016 | 3,3-diphenyl-2-propen-1-ol | C15H14O | 详情 | 详情 | |
| (IV) | 61017 | 1-(3-chloro-1-phenyl-1-propenyl)benzene | C15H13Cl | 详情 | 详情 | |
| (V) | 61018 | 1-(3,9-diazabicyclo[3.3.1]non-3-yl)-1-propanone | C10H18N2O | 详情 | 详情 |