2′-Deoxyadenosine Bearing Hydrophobic Carborane Pharmacophore

Abstract

Modification of 2′-deoxyadenosine at position 8 with para-carborane boron cluster is described. Incorporation of boron cluster into nucleic base has been accomplished using Sonogashira palladium-catalyzed cross-coupling reaction or, alternatively, Huisgen “click” type reaction. These are the first examples of adenosine derivatives with hydrophobic carborane pharmacophore attached to purine base.

Keywords:

• Carborane
• nucleoside
• pharmacophor
• “click”
• chemistry

This work has been supported in part by the Polish Ministry Education and Sciences grant number 1 T09A 121 30 and by internal grant from the Center of Medical Biology PAS. Authors thank Prof. J. Plešek and Dr. Bohümir Grüner for kind gift of 10-dioxane-7,8-dicarba-nido-undecaborane.