Justus-liebig-universitaet Giessen

Jüstus-Liebig-Universität Giessen

Elisa Franzmann

Wolfgang Maison

Faiza Khalil

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&#x2014;C[(CH)&#x2014;YZ], wherein X stands for a group &#x2014;(CH)&#x2014;R, wherein p=0 to 10 and Ris selected from &#x2014;H, &#x2014;NH, &#x2014;NO, &#x2014;OH, &#x2014;SH, &#x2014;O&#x2014;NH, &#x2014;NH&#x2014;NH, &#x2014;N&#x2550;C&#x2550;S&#x2014;, &#x2014;N&#x2550;C&#x2550;O&#x2014;, &#x2014;CH&#x2550;CH, &#x2014;C&#x2261;CH, &#x2014;COOH, &#x2014;(C&#x2550;O)H, &#x2014;(C&#x2550;O)RY stands for &#x2014;CH&#x2014;, &#x2014;CH&#x2550;CH&#x2014;, &#x2014;C&#x2261;C&#x2014;, &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;S&#x2014;S&#x2014;, &#x2014;NH&#x2014;, &#x2014;O&#x2014;NH&#x2014;, &#x2014;NH&#x2014;O&#x2014;, &#x2014;HC&#x2550;N&#x2014;O&#x2014;, &#x2014;O&#x2014;N&#x2550;CH&#x2014;, &#x2014;NR&#x2014;, -Aryl-, -Heteroaryl-, &#x2014;(C&#x2550;O)&#x2014;, &#x2014;O&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;O&#x2014;, &#x2014;NH&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;NH&#x2014;, &#x2014;NR&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;NR&#x2014;, &#x2014;NH&#x2014;(C&#x2550;O)&#x2014;NH&#x2014;, &#x2014;NH&#x2014;(C&#x2550;S)&#x2014;NH&#x2014;, Rstands for an aryl 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&#x2014;C[(CH)&#x2014;Y']with a reagent Y&#x2033;Z to the corresponding compound X&#x2014;C[(CH)&#x2014;YZ]and subsequent purification of the reaction product. Y&#x2032; and Y&#x2033; 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.

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

The present invention describes tripodal bisphosphonate 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. A fourth remaining position of the flexible framework is suitable to be optionally functionalized by so-called click reactions, for example with biomolecules, polyethylene glycol or active agents. The compounds according to the present invention have the general formula X&#x2014;C{(CH)&#x2014;Y&#x2014;C[PO(OH)]R}, wherein X stands for a group &#x2014;(CH)&#x2014;R, wherein p=0 to 10 and Ris selected from &#x2014;H, &#x2014;NH, &#x2014;NO, &#x2014;OH, &#x2014;SH, &#x2014;O&#x2014;NH, &#x2014;NH&#x2014;NH, &#x2014;N&#x2550;C&#x2550;S&#x2014;, &#x2014;N&#x2550;C&#x2550;O&#x2014;, &#x2014;CH&#x2550;CH, &#x2014;C&#x2261;CH, &#x2014;COOH, &#x2014;(C&#x2550;O)H, &#x2014;(C&#x2550;O)RY stands for &#x2014;CH&#x2014;, &#x2014;CH&#x2550;CH&#x2014;, &#x2014;C&#x2261;C&#x2014;, &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;S&#x2014;S&#x2014;, &#x2014;NH&#x2014;, &#x2014;O&#x2014;NH&#x2014;, &#x2014;NH&#x2014;O&#x2014;, &#x2014;HC&#x2550;N&#x2014;O&#x2014;, &#x2014;O&#x2014;N&#x2550;CH&#x2014;, &#x2014;NR&#x2014;, -aryl-, -heteroaryl-, &#x2014;(C&#x2550;O)&#x2014;, &#x2014;O&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;O&#x2014;, &#x2014;NH&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;NH&#x2014;, &#x2014;NR&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;NR&#x2014;, &#x2014;NH&#x2014;(C&#x2550;O)&#x2014;NH&#x2014;, &#x2014;NH&#x2014;(C&#x2550;S)&#x2014;NH&#x2014;, Rrepresents a hydrogen atom or a hydroxy group, Rstands for a linear or branched alkyl group and Rfor a linear or branched alkyl group or an aryl group. The production of the compounds occurs by reacting a compound X&#x2014;C[(CH)&#x2014;Y']with a reagent Y&#x2033;C[PO(OH)]Rto the corresponding compound X&#x2014;C{(CH)&#x2014;Y&#x2014;C[PO(OH)]R}and subsequent purification of the reaction product. Y&#x2032; and Y&#x2033; 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.

Tripodal bisphosphonate derivatives

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)&#x2014;YZ], wherein A stands for the adamantyl skeleton, X stands for a group &#x2014;(CH)&#x2014;R, wherein p=0 to 10 and Ris selected from &#x2014;H, &#x2014;NH, &#x2014;NO, &#x2014;OH, &#x2014;SH, &#x2014;O&#x2014;NH, &#x2014;NH&#x2014;NH, &#x2014;N&#x2550;C&#x2550;S&#x2014;, &#x2014;N&#x2550;C&#x2550;O&#x2014;, &#x2014;CH&#x2550;CH, &#x2014;C&#x2261;CH, &#x2014;COOH, &#x2014;(C&#x2550;O)H, &#x2014;(C&#x2550;O)RY stands for &#x2014;CH&#x2014;, &#x2014;CH&#x2550;CH&#x2014;, &#x2014;C&#x2261;C&#x2014;, &#x2014;O&#x2014;, &#x2014;S&#x2014;, &#x2014;S&#x2014;S&#x2014;, &#x2014;NH&#x2014;, &#x2014;O&#x2014;NH&#x2014;, &#x2014;NH&#x2014;O&#x2014;, &#x2014;HC&#x2550;N&#x2014;O&#x2014;, &#x2014;O&#x2014;N&#x2550;CH&#x2014;, &#x2014;NR&#x2014;, -aryl-, -heteroaryl-, &#x2014;(C&#x2550;O)&#x2014;, &#x2014;O&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;O&#x2014;, &#x2014;NH&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;NH&#x2014;, &#x2014;NR&#x2014;(C&#x2550;O)&#x2014;, &#x2014;(C&#x2550;O)&#x2014;NR&#x2014;, &#x2014;NH&#x2014;(C&#x2550;O)&#x2014;NH&#x2014;, &#x2014;NH&#x2014;(C&#x2550;S)&#x2014;NH&#x2014;, 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)&#x2014;Y']with a reagent Y&#x2033;Z to the corresponding compound X-Ad[(CH)&#x2014;YZ]and subsequently purifying the reaction product. Y&#x2032; and Y&#x2033; 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.

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Wettenberg-Wiβmar, Germany

Elisa Franzmann