Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles.
Dicarba-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.
Radiochemistry and Nuclear Imaging Group, CIC biomaGUNE, Paseo Miramon 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain. kbgona@cicbiomagune.es.
Kiran B
KB
Gona
Radiochemistry and Nuclear Imaging Group, CIC biomaGUNE, Paseo Miramon 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain. vnpgona@cicbiomagune.es.
Jaya Lakshmi V N P
JL
Thota
Radiochemistry and Nuclear Imaging Group, CIC biomaGUNE, Paseo Miramon 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain. zbaz@cicbiomagune.es.
Zuriñe
Z
Baz
Radiochemistry Platform, CIC biomaGUNE, Paseo Miramón 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain. vgomez@cicbiomagune.es.
Vanessa
V
Gómez-Vallejo
Radiochemistry and Nuclear Imaging Group, CIC biomaGUNE, Paseo Miramon 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain. jllop@cicbiomagune.es.
Jordi
J
Llop
D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002250:Carbon Radioisotopes / Q000737:chemistry; D049268:Positron-Emission Tomography / Q000379:methods*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000737:chemistry
C111133:2-(4-aminophenyl)benzothiazole; D052160:Benzothiazoles; D001896:Boron Compounds; D002250:Carbon Radioisotopes; D019275:Radiopharmaceuticals