| 摘要 |
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[(CH2)n—YZ]3, wherein A stands for the adamantyl skeleton, 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 alkyl 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-Ad[(CH2)n—Y′]3 with a reagent Y″Z to the corresponding compound X-Ad[(CH2)n—YZ]3 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. |
| 主权项 |
1. A compound according to formula (I) wherein
n is an integer between 0 and 10,Y is a bond, —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—, or —NH—(C═S)—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 10R5 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 suitable to be protected by a protective group, —N3, —OR6, —COOR6, —NHR6, —NR6R7, —CO—NHR6, —CONR6R7, —NH—CO—R6, or 4-(2,5-dioxopyrrol-1-yl), andR6 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. |
