Indicator platform
AssigneeBiosynth AG
InventorsUrs Spitz, Lukas Wick, Alexander Bayer, Christophe Weymuth, Günter Schabert
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Abstract
A novel indicator platform comprises a plurality of 1H-lndol-3-yl indicator compounds that are capable of converting to a signalophore compound in response to an external stimulus. In one class of indicator compounds, the resulting signalophores are 2-benzylideneindoline compounds that are formed by an intermolecular Aldol-type process; in a further class of indicator compounds, the resulting signalophores are 10H-indolo[1,2-a]indole compounds that are formed by an intramolecular Aldol-type process. The indicators can be used in a wide array of applications relating, for example, to biological systems or optical data storage.
Claims15
An indicator system for detecting an external stimulus, comprising an indicator compound of the general formula
- wherein:
- X is O, NH or S;
- LG is a labile group with the X-LG moiety being susceptible to conversion by action of said external stimulus;
- R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, C1-4 alkyl;
- C1-4 alkoxy;
- fused or linearly connected aryl;
- fused or linearly connected heteroaryl;
- halogen;
- cyano;
- nitro;
- formyl;
- and optionally substituted amino, carboxy, carbonyl, hydroxy and sulfonyl;
- R5 is either hydrogen or R12, wherein R12 is
- wherein:
- Z is O, NH or S;
- R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, C1-4 alkyl;
- C1-4 alkoxy;
- fused or linearly connected aryl;
- fused or linearly connected heteroaryl;
- halogen;
- cyano;
- nitro;
- formyl;
- and optionally substituted amino, carboxy, carbonyl, hydroxy and sulfonyl;
- and wherein, if R5 is hydrogen, the indicator system further comprises an acceptor compound of the general formula
- wherein:
- Ra and Rb are independently selected from hydrogen and C1-4 alkyl.
A method of preparing an indicator compound of the general formula
- wherein:
- X is O, NH or S;
- LG is a labile group with the X-LG moiety being susceptible to conversion by action of said external stimulus;
- R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, C1-4 alkyl;
- C1-4 alkoxy;
- fused or linearly connected aryl;
- fused or linearly connected heteroaryl;
- halogen;
- cyano;
- nitro;
- formyl;
- and optionally substituted amino, carboxy, carbonyl, hydroxy and sulfonyl;
- and R5 is R12 which is
- wherein:
- Z is O, NH or S;
- and wherein R6, R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, C1-4 alkyl;
- C1-4 alkoxy;
- fused or linearly connected aryl;
- fused or linearly connected heteroaryl;
- halogen;
- cyano;
- nitro;
- formyl;
- and optionally substituted amino, carboxy, carbonyl, hydroxy and sulfonyl;
- characterized in that it comprises the step of N-arylation of an indoxyl compound of the general formula
- with a benzene derivative of the general formula
- wherein Q is a leaving group selected from iodo, bromo, triflate and tosylate.
A compound of structural formula
- wherein
- X is O, NH or S
- R1, R2, R3, R4, R6, R7, R8, R9 and R13 are independently selected from the group consisting of hydrogen, C1-4 alkyl;
- C1-4 alkoxy;
- fused or linearly connected aryl;
- fused or linearly connected heteroaryl;
- halogen;
- cyano;
- nitro;
- formyl;
- and optionally substituted amino, carboxy, carbonyl, hydroxy and sulfonyl, with the exception of the following compounds
Dependencies are inferred from the claim text.