Synthesis of trivalent flexible frameworks with ligands comprising catechol units for functionalizing surfaces

摘要

The present invention describes tripodal catechol derivatives with a flexible basic framework for the functionalization of surfaces, and methods for their production and use. The central atom of the flexible framework is hereby a tertiary aliphatic carbon atom. The remaining fourth bridgehead position is easily suitable to be further functionalized via so-called click reactions, e.g. with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents.;The compounds according to the present invention have the general formula X—C[(CH2)n—YZ]3, wherein X stands for a group —(CH2)p—R5, wherein p=0 to 10 and R5 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)R6Y stands for —CH2—, —CH═CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HC═N—O—, —O—N═CH—, —NR1—, -Aryl-, -Heteroaryl-, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —NH—(C═O)—, —(C═O)—NH—, —NR1—(C═O)—, —(C═O)—NR1—, —NH—(C═O)—NH—, —NH—(C═S)—NH—, R1 stands for an aryl group, R6 for 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—C[(CH2)n—Y′]3 with a reagent Y″Z to the corresponding compound X—C[(CH2)n—YZ]3 and subsequent purification of 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.

主权项

1. A compound according to formula (I)wherein
n is an integer between 0 and 10, Y is a bond, —CH2—, —NR1—, —NH—(C═O)—, or —(C═O)—NH— R1 is a linear alkyl group with 1 to 10 C atoms, or for a branched or cyclic alkyl group with 3 to 10 C atoms, Z is selected from m is an integer between 0 and 10, R2 is —H, —OH or —COOH, R3 is —H or —OH, A is a bond or —(C═O)—, R4 is —H or X is —(CH2)p—R5; a branched alkyl, alkenyl or alkynyl group with 3 to 10 C atoms; a cyclic alkyl, alkenyl or alkynyl group with 3 to 10 C atoms; or an aryl or heteroaryl group, p is an integer between 0 and 10 R5 is —H, —NH2, —NO2, —OH, —SH, —O—NH2, —NH—NH2, —N═C═S, —NC═O, —CH═CH2, —C≡CH, —COOH, —(C═O)H, or —(C═O)R6, wherein the hydroxy, thio, amino or C═O groups are optionally protected by a protective group, —N3, —OR6, —COOR6, —NHR6, —NR6R7, —CO—NHR6, —CONR6R7, —NH—CO—R6, or 4-(2,5-dioxopyrrol-1-yl), and R6 and R7 each, independently, is a linear alkyl group with 1 to 10 C atoms, a linear alkenyl or alkynyl group with 2 to 10 C atoms, or a branched alkyl, alkenyl or alkynyl group with 3 to 10 C atoms,wherein, if X is a branched alkyl, alkenyl or alkynyl group, a cyclic alkyl or alkenyl group, an aryl or heteroaryl group, then one C atom of this group X is optionally substituted with R5.