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【结 构 式】 
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【药物名称】Altropane, IACFT, Altropane 【化学名称】(1R,2S,3S,5S)-3-(4-Fluorophenyl)-8-[3-iodo-2(E)-propenyl]-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester 【CA登记号】180468-34-2, 208517-65-1 ([123I]-labeled), 180268-78-4 ([125I]-isotope) 【 分 子 式 】C18H21FINO2 【 分 子 量 】429.27637 |
【开发单位】MDS Nordion (Supplier), Organix (Originator), Boston Life Sciences (Licensee) 【药理作用】Diagnostic Agents, Drugs Acting on Dopaminergic Transmission |
合成路线1
Addition of tributyltin hydride to the triple bond of propargyl alcohol (I) in the presence of AIBN provided a mixture of (Z)-(II) and (E)-3-(tributylstannyl)-2-propen-1-ol (III), which were separated by column chromatography. The desired (E)-allyl alcohol (III) was further converted to the corresponding chloride (IV) by treatment with PPh3 in refluxing CCl4. Alkylation of the nortropane derivative (V) with chloride (IV) in the presence of celite-supported KF furnished the N-(tributylstannyl)propenyl nortropane (VI). The target iodinated compound was then prepared by treatment of (VI) with N-iodosuccinimide.
| 【2】 Elmaleh, D.R.; Madras, B.K.; Meltzer, P.; Hanson, R.N. (General Hospital Corporation; Harvard College; Northeastern University); Substd. 2-carboxyalkyl-3-(fluorophenyl)-8-(3-haloprofen-2-yl) nortropanes and their use as imaging agents for neurodegenerative disorders. EP 0734385; EP 1081147; WO 9511901 . |
| 【1】 Elmaleh, D.R.; et al.; Preparation and biological evaluation of iodine-125-IACFT: A selective SPECT agent for imaging dopamine transporter sites. J Nucl Med 1996, 37, 7, 1197. |
| 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) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
| (II) | 52939 | (Z)-3-(tributylstannyl)-2-propen-1-ol | C15H32OSn | 详情 | 详情 | |
| (III) | 52942 | (E)-3-(tributylstannyl)-2-propen-1-ol | n/a | C15H32OSn | 详情 | 详情 |
| (IV) | 50995 | tributyl[(E)-3-chloro-1-propenyl]stannane | C15H31ClSn | 详情 | 详情 | |
| (V) | 52940 | methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate | n/a | C15H18FNO2 | 详情 | 详情 |
| (VI) | 52941 | methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-(tributylstannyl)-2-propenyl]-8-azabicyclo[3.2.1]octane-2-carboxylate | n/a | C30H48FNO2Sn | 详情 | 详情 |