Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles
AbstractDicarba-closo-dodecaboranes, commonly known as carboranes, possess unique physico-chemical properties and can be used as hydrophobic moieties during the design of new drugs or radiotracers. In this work, we report the synthesis of two analogues of 2-(4-aminophenyl)benzothiazole (a compound that was found to elicit pronounced inhibitory effects against certain breast cancer cell lines in vitro) in which the phenyl ring has been substituted by a m-carborane cage. Two different synthetic strategies have been used. For the preparation of 1-(9-amino-1,7-dicarba-closo-dodecaboran-1-yl)-benzo-thiazole, the benzothiazole group was first introduced on one of the cluster carbon atoms of m-carborane and the amine group was further attached in three steps. For the synthesis of 1-(9-amino-1,7-dicarba-closo-dodecaboran-1-yl)-6-hydroxybenzothiazole, iodination was performed before introducing the benzothiazole group, and the amino group was subsequently introduced in six steps. Both compounds were radiolabelled with carbon-11 using [11C]CH3OTf as the labelling agent. Radiolabelling yields and radiochemical purities achieved should enable subsequent in vitro and in vivo investigations. View Full-Text
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Gona, K.B.; Thota, J.L.V.N.P.; Baz, Z.; Gómez-Vallejo, V.; Llop, J. Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles. Molecules 2015, 20, 7495-7508.
Gona KB, Thota JLVNP, Baz Z, Gómez-Vallejo V, Llop J. Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles. Molecules. 2015; 20(5):7495-7508.Chicago/Turabian Style
Gona, Kiran B.; Thota, Jaya L.V.N.P.; Baz, Zuriñe; Gómez-Vallejo, Vanessa; Llop, Jordi. 2015. "Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles." Molecules 20, no. 5: 7495-7508.