含酸敏性连接基的10-(2-烷基氨基-2-氧代乙基)-1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸衍生物的改进合成方法
IMPROVED SYNTHESIS OF 10-(2-ALKYLAMINO-2-OXOETHYL)-1,4,7,10-TETRAAZACYCLODODECANE-1,4,7-TRIACETIC ACID DERIVATIVES BEARING ACID-SENSITIVE LINKERS.
作者信息
Jagadish Bhumasamudram, Ozumerzifon Tarik J, Roberts Sue A, Hall Gabriel B, Mash Eugene A, Raghunand Natarajan
机构信息
Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721-0041 USA.
Department of Medical Imaging, University of Arizona, Tucson, AZ 85721-0041 USA ; Arizona Cancer Center, University of Arizona, Tucson, AZ 85721-0041 USA.
出版信息
Synth Commun. 2014;44(3). doi: 10.1080/00397911.2013.813547.
Alkylation of the hydrobromide salts of 1,4,7-tris(methoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane and 1,4,7-tris(ethoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane with appropriate α-bromoacetamides, followed by hydrolysis, provides convenient access to 10-(2-alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid derivatives that contain acid-sensitive functional groups. The utility of the method is demonstrated by improved syntheses of two known DOTA monoamides bearing acid-sensitive ω-tritylthio alkyl chains in much higher yields based on cyclen as the starting material.
1,4,7-三（甲氧羰基甲基）-1,4,7,10-四氮杂环十二烷和1,4,7-三（乙氧羰基甲基）-1,4,7,10-四氮杂环十二烷的氢溴酸盐与适当的α-溴代乙酰胺进行烷基化反应，随后水解，可方便地得到含有酸敏感官能团的10-（2-烷基氨基-2-氧代乙基）-1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸衍生物。以环糊精为起始原料，通过改进合成两种带有酸敏感ω-三苯甲基硫烷基链的已知DOTA单酰胺，以更高的产率证明了该方法的实用性。
Zotero 插件