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Molecules 2015, 20(5), 7495-7508; doi:10.3390/molecules20057495

Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles

1
Radiochemistry and Nuclear Imaging Group, CIC biomaGUNE, Paseo Miramon 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain
2
Radiochemistry Platform, CIC biomaGUNE, Paseo Miramón 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: John Spencer
Received: 13 March 2015 / Revised: 15 April 2015 / Accepted: 20 April 2015 / Published: 23 April 2015
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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Abstract

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. View Full-Text
Keywords: m-carborane; benzothiazole; positron emission tomography; radiolabelling; carbon-11 m-carborane; benzothiazole; positron emission tomography; radiolabelling; carbon-11
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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