Synthesis of tripodal catechol derivatives having an adamantyl basic framework for functionalizing surfaces

Abstract

The present invention describes tripodal catechol derivatives with an adamantyl basic framework for the functionalization of surfaces, methods for their production and use. The remaining fourth bridgehead position is easily suitable to be further functionalised via so-called click reactions, by way of example with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents. The compounds according to the present invention have the general formula X-Ad[(CH)—YZ], wherein A stands for the adamantyl skeleton, X stands for a group —(CH)—R, wherein p=0 to 10 and Ris selected from —H, —NH, —NO, —OH, —SH, —O—NH, —NH—NH, —N═C═S—, —N═C═O—, —CH═CH, —C≡CH, —COOH, —(C═O)H, —(C═O)RY stands for —CH—, —CH═CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HC═N—O—, —O—N═CH—, —NR—, -aryl-, -heteroaryl-, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —NH—(C═O)—, —(C═O)—NH—, —NR—(C═O)—, —(C═O)—NR—, —NH—(C═O)—NH—, —NH—(C═S)—NH—, Rstands for an alkyl group, Rfor an alkyl, alkenyl, alkynyl, aryl or heteroaryl group, and Z stands for a catechol derivative. The production of the compounds occurs by reacting a compound X-Ad[(CH)—Y']with a reagent Y″Z to the corresponding compound X-Ad[(CH)—YZ]and subsequently purifying the reaction product. Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalize surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.