SYNTHESIS OF TRIPODAL BISPHOSPHONATE DERIVATIVES HAVING AN ADAMANTYL BASIC FRAMEWORK FOR FUNCTIONALIZING SURFACES

摘要

The present invention relates to tripodal bisphosphonate derivatives having an adamantyl basic framework for functionalizing surfaces, to methods for the production and to the use thereof. The remaining fourth bridgehead position of the adamantane framework can optionally be functionalized by so-called click reactions, for example by using biomolecules, polyethylene glycol or active substances. The compounds according to the invention have the general formula X-Ad{(CH2)n-Y-C[PO(OH)2]2R1}3, wherein Ad represents the adamantyl framework, X represents a group -(CH2)p-R3, in which p = 0-10 and R3 is selected from -H, -NH2, -NO2, -OH, -SH, -O-NH2, -NH-NH2, -N=C=S-, -N=C=O-, -CH=CH2, -C=CH, -COOH, -(C=O)H, -(C=O)R4, Y represents -CH2-, -CH=CH-, -C=C-, -O-, -S-, -S-S-, -NH-, -O-NH-, -NH-O-, -HC=N-O-, -O-N=CH-, -NR2-, -aryl-, -heteroaryl-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -NH-(C=O)-, -(C=O)-NH-, -NR2-(C=O)-, -(C=O)-NR2-, -NH-(C=O)-NH-, -NH-(C=S)-NH-, R1 represents a hydrogen atom or a hydroxy group, R2 represents a linear or branched alkyl group, and R4 represents a linear or branched alkyl or aryl group. The compounds are produced by reacting a compound X-Ad[(CH2)n-Y']3 with a reagent Y"C[PO(OH)2]2R1 to form the corresponding compound X-Ad{(CH2)n-Y-C[PO(OH)2]2R1}3 and the reaction product is subsequently purified. Y' and Y'' are precursors of Y. The compounds according to the invention of formula (I) can be used in a method for functionalizing surfaces. Optionally, the group X of the compounds according to the invention can be coupled to an effector, for example by means of click chemistry.