Next Article in Journal
Significance of β-Galactoside α2,6 Sialyltranferase 1 in Cancers
Next Article in Special Issue
Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014
Previous Article in Journal
Inhibition of Oncogenic Transcription Factor REL by the Natural Product Derivative Calafianin Monomer 101 Induces Proliferation Arrest and Apoptosis in Human B-Lymphoma Cell Lines
Previous Article in Special Issue
Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones
Open AccessArticle

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
Molecules 2015, 20(5), 7495-7508; https://doi.org/10.3390/molecules20057495
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)
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
Show Figures

Figure 1

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.

Show more citation formats Show less citations formats

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Back to TopTop