111In-DTPA-Abeta(3-40), -Drug Synthesis Database

【结构式】

【药物名称】111In-DTPA-Abeta(3-40)

【化学名称】[N-[2-[N-[2-[N,N-Bis(carboxymethyl)amino]ethyl]-N-(carboxymethyl)amino]ethyl]-N-(carboxymethyl)glycyl-L-glutamyl-L-phenylalanyl-L-arginyl-L-histidyl-L-aspartyl-L-seryl-glycyl-L-tyrosyl-L-glutamyl-L-valyl-L-histidyl-L-histidyl-L-glutaminyl-L-lysyl-L-leucyl-L-valyl-L-phenylalanyl-L-phenylalanyl-L-alanyl-L-glutamyl-L-aspartyl-L-valyl-glycyl-L-seryl-L-asparaginyl-L-lysyl-glycyl-L-alanyl-L-isoleucyl-L-isoleucyl-glycyl-L-leucyl-L-methionyl-L-valyl-glycyl-glycyl-L-valyl-L-valinato(3-)]indium-111In

【CA登记号】

【分子式】C₂₀₁H₃₀₃InN₅₄O₆₃S

【分子量】4627.04406

【开发单位】University of California, Los Angeles (Originator), University of Cincinnati (Originator), University of Minnesota (Originator)

【药理作用】Diagnostic Agents, Diagnostic for Alzheimer's Disease, Metal Complexes, Polypeptides

合成路线1 合成路线2

合成路线1

The resin-bound A-beta(3-40) amyloid peptide (I) is prepared by solid-phase synthesis, employing Fmoc chemistry. Acylation of the peptide-resin (I) with diethylenetriaminepentaacetic (DTPA) dianhydride (II) gives rise to the peptide DTPA-amide (III), which is further liberated from the resin to produce (IV)

参考文献中间体

【1】 Marshall, J.R.; et al.; Noninvasive imaging of peripherally injected Alzheimer's disease type synthetic A beta amyloid in vivo. Bioconjugate Chem 2002, 13, 2, 276.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	49150	Diethylenetriaminepentaacetic acid; N,N-Bis[2-(2,6-dioxomorpholino)ethyl]glycine	23911-26-4	C₁₄H₁₉N₃O₈	详情	详情

合成路线2

2-Methylimidazole (I) is converted into the bisulfate salt, and then nitrated by means of a sulfonitric mixture in Ac2O to produce 2-methyl-4-nitroimidazole (II) . In a variant of this procedure, 2-methylimidazole (I) is nitrated by using a ferric nitrate-tonsyl adduct in several solvents. Imidazole (II) is then regioselectively alkylated with boiling 2-chloroethanol to produce the title compound. Alternatively, the alkylation of (II) has been reported by treatment with ethylene oxide (III) under acidic conditions.

参考文献中间体

【1】 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 .
【2】 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成

Extended Information

Drug NewChemical Entity Original Patent(1)