MP-2269
Chemical Name: Tetrasodium [6-[2-[bis(carboxylatomethyl)amino]ethyl]-7-carboxylato-3-(carboxylatomethyl)-12-[(4-pentylbicyclo[2.2.2]oct-1-ylcarbonyl)-L-aspartyl-L-aspartyl]-3,6,12-triazadodecanoato(7-)]gadolinate
CAS No. 207917-71-3 (ligand)
项目整合开发状态: Preclinical
项目研究机构: Mallinckrodt (Originator)
合成路线:4-Pentylbicyclo[2.2.2]octane-1-carboxylic acid (I) was converted to the corresponding acid chloride with SOCl2 and then coupled to L-aspartic acid beta-tert-butyl ester (II) to afford amide (III).Subsequent coupling of (III) with further L-aspartic acid beta-tert-butyl ester (II) in the presence of DCC and NHS produced diamide (IV).This was then condensed with (aminobutyl)diethylenetriamino-pentaacetic acid penta-tert-butyl ester (V) to provide (VI).
合成路线:After deprotection of the tert-butyl ester groups of (VI) with HCl in dioxan,the resulting heptacarboxylic acid (VII) was treated with gadolinium (III) oxide at a controlled pH value to furnish the target gadolinium chelate.
📌 参考资料/链接：
参考文献标题:Magnetic resonance blood pool agents
文献作者:Woulfe,S.R.(Mallinckrodt Medical Inc.)
参考来源:WO 9820908
📄 详细内容
合成路线:4-Pentylbicyclo[2.2.2]octane-1-carboxylic acid (I) was converted to the corresponding acid chloride with SOCl2 and then coupled to L-aspartic acid beta-tert-butyl ester (II) to afford amide (III).Subsequent coupling of (III) with further L-aspartic acid beta-tert-butyl ester (II) in the presence of DCC and NHS produced diamide (IV).This was then condensed with (aminobutyl)diethylenetriamino-pentaacetic acid penta-tert-butyl ester (V) to provide (VI).
合成路线:After deprotection of the tert-butyl ester groups of (VI) with HCl in dioxan,the resulting heptacarboxylic acid (VII) was treated with gadolinium (III) oxide at a controlled pH value to furnish the target gadolinium chelate.
参考文献标题:Synthesis and preliminary evaluation of MP-2269: A novel,nonaromatic small-molecule blood-pool MR contrast agent
文献作者:Wallace,R.A.; Haar,J.P.Jr.; Miller,D.B.; Woulfe,S.R.; Polta,J.A.; Galen,K.P.; Hynes,M.R.; Adzamli,K.
参考来源:Magn Reson Med 1998,40(5),733