Abstract
AbstractThe 11C labeled 1-aminocyclobutanecarboxylic acid (ACBC) has been previously reported to be more accurate than 18F-FDG for diagnosing recurrent brain tumors. The tumor uptake of the 11C labeled ACBC was very impressive, with the tumor/normal tissue ratio as high as 10:1. In this study, the boronated derivative of the amino acid selected with high lipophilicity was proposed to develop as the BNCT (boron neutron capture therapy) drug for hepatoma, instead of brain tumor. 1-Amino-3-[7-(4-boronophenyl)heptyl]cyclobutane-carboxylic acid was chosen and studied for the purpose.The compound has been synthesized via seven steps. The conditions proceeding from the first step to the final product have been systematically investigated. Initially, 9-(4-bromophenyl)-1-nonene was prepared under a crucial condition at -70℃and under argon atmosphere by the reaction of 4-bromobenzyl bromide with 7-octenyl magnesium bromide. The key step was the preparation of the precursor p-boronophenyl-heptyl-cyclobutane ethylene ketal, which was subsequently converted to the desired boronated amino acid via the Bucherer-Strecker reaction. 1H-NMR and 13C-NMR were used to identify all the compounds synthesized in the process. The final product was furthermore purified for a preliminary study as a BNCT agent including cell uptake, animal biodistribution etc.