Gona Kiran B, Thota Jaya Lakshmi V N P, Baz Zuriñe, Gómez-Vallejo Vanessa, Llop Jordi
Radiochemistry and Nuclear Imaging Group, CIC biomaGUNE, Paseo Miramon 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain.
Radiochemistry Platform, CIC biomaGUNE, Paseo Miramón 182, Parque Tecnológico de San Sebastián, San Sebastián 20009, Spain.
Molecules. 2015 Apr 23;20(5):7495-508. doi: 10.3390/molecules20057495.
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.
二碳-闭式-十二硼烷，通常称为碳硼烷，具有独特的物理化学性质，在新药或放射性示踪剂的设计中可用作疏水基团。在这项工作中，我们报告了两种2-(4-氨基苯基)苯并噻唑类似物（一种在体外对某些乳腺癌细胞系有明显抑制作用的化合物）的合成，其中苯环已被间碳硼烷笼取代。我们使用了两种不同的合成策略。为了制备1-(9-氨基-1,7-二碳-闭式-十二硼烷-1-基)苯并噻唑，首先在间碳硼烷的一个簇碳原子上引入苯并噻唑基团，然后通过三步进一步连接氨基。为了合成1-(9-氨基-1,7-二碳-闭式-十二硼烷-1-基)-6-羟基苯并噻唑，在引入苯并噻唑基团之前进行碘化反应，随后通过六步引入氨基。两种化合物均使用[11C]CH3OTf作为标记剂用碳-11进行放射性标记。所获得的放射性标记产率和放射化学纯度应能支持后续的体外和体内研究。
