Compounds with semiochemical properties and biosensors

A compound of Formula I, or a salt, a solvate, a tautomer, a stereoisomer or a deuterated analogue thereof:

• wherein,
• X is C═O, C═S, C═S+—O—, C(R3)(R4), C═C(R5)(R6) or C═N(R7);
• in ring A:
• (i) Y1 is C(R8)(R9), S, S(O), S(O)2 or N(R10), Y2 is C(R11)(R12) and Y3 is C(R13);
• or
• (ii) Y1 is C(R8)(R9), S, S(O), S(O)2 or N(R10), Y2 is C(R11) and Y3 is C;
• or
• (iii) Y1 is C(R8) or N, Y2 is C(R11) and Y3 is C(R13);
• R1 is independently selected from hydroxy, halogen, cyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocycloalkyl, optionally substituted alkoxy, optionally substituted alkanoyl, optionally substituted amino, optionally substituted aryl and optionally substituted heteroaryl;
• R2 is independently selected from hydroxy, halogen, cyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocycloalkyl, optionally substituted alkoxy, optionally substituted alkanoyl, optionally substituted amino, optionally substituted aryl and optionally substituted heteroaryl;
• R3 and R4 are independently selected from hydrogen, hydroxy, halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkanoyl and optionally substituted amino, or R3 and R4 together with the carbon atom to which they are attached form a 3-membered or 4-membered optionally substituted carbocyclic or optionally substituted heterocyclic ring;
• R5 to R13 are independently selected from hydrogen, hydroxy, halogen, cyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocycloalkyl, optionally substituted alkoxy, optionally substituted alkanoyl, optionally substituted amino, optionally substituted aryl and optionally substituted heteroaryl;
• and
• represents a single or double bond to maintain correct atom valencies for Y1, Y2 and Y3 in ring A.

A compound of Formula IA, or a salt, a solvate, a tautomer, a stereoisomer or a deuterated analogue thereof:

• wherein,
• X is C═O, C═S, C═S+—O—, C(R3)(R4), C═C(R5)(R6) or C═N(R7);
• in ring A:
• (i) Y2 is C(R11)(R12) and Y3 is C(R13);
• or
• (ii) Y2 is C(R11) and Y3 is C;
• R1 is independently selected from hydroxy, halogen, cyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocycloalkyl, optionally substituted alkoxy, optionally substituted alkanoyl, optionally substituted amino, optionally substituted aryl and optionally substituted heteroaryl;
• R2 is independently selected from hydroxy, halogen, cyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocycloalkyl, optionally substituted alkoxy, optionally substituted alkanoyl, optionally substituted amino, optionally substituted aryl and optionally substituted heteroaryl;
• R3 and R4 are independently selected from hydrogen, hydroxy, halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkanoyl and amino, or R3 and R4 together with the carbon atom to which they are attached form a 3-membered or 4-membered optionally substituted carbocyclic or optionally substituted heterocyclic ring;
• R5 to R7 and R11 to R13 are independently selected from hydrogen, hydroxy, halogen, cyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocycloalkyl, optionally substituted alkoxy, optionally substituted alkanoyl, optionally substituted amino, optionally substituted aryl and optionally substituted heteroaryl;
• and
• represents a single or double bond;
• wherein the compound of Formula IA is not:

A biosensor for detecting an analyte in a sample, the biosensor comprising:

• a protein having an amino acid sequence as defined in SEQ ID NO:
• 6, or a fragment or variant thereof;
• and
• a signal generator, wherein the signal generator is configured to output a signal when the analyte is bound to the protein.