Peptidomimetics possessing photo-controlled biological activity

A photo-switchable molecular system comprising a scheme comprising formulae IVa and IVb

• wherein
• R1 and R4 are independently selected from the group consisting of H, an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
• R2 and R3 are independently selected from the group consisting of an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
• X represents —(CHxFy)z—, wherein x+y=2, x=0, 1 or 2, y=0, 1 or 2 and z=2 to 4;
• and
• Y1 and Y2 are independently selected from S, SO2, N, N-alkyl, or 0.

A method of photo-isomerizing an active compound, the method comprising:

• applying ultraviolet (UV) light to a compound of formula IVa to form a compound of formula IVb
• wherein
• R1 and R4 are independently selected from the group consisting of H, an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
• R2 and R3 are independently selected from the group consisting of an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
• X represents —(CHxFy)z—, wherein x+y=2, x=0, 1 or 2, y=0, 1 or 2 and z=2 to 4;
• and
• Y1 and Y2 are independently selected from S, SO2, N, N-alkyl, or 0.

An intermediate compound represented by the general formula II or a salt thereof:

• usable for the synthesis of a peptidomimetic compound represented by the general formula Ia:
• wherein
• ZZ represents a protecting group;
• R1 and R4 are independently selected from the group consisting of H, an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
• R2 and R3 are independently selected from the group consisting of an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
• X represents —(CHxFy)z—, wherein x+y=2, x=0, 1 or 2, y=0, 1 or 2 and z=2 to 4;
• Y1 and Y2 are independently selected from the group consisting of S, SO2, N, N-alkyl, or 0;
• P1 and P3 each independently represents a single amino acid residue or a peptide sequence of two or more amino acid residues;
• P2 is absent or represents a single amino acid residue or a peptide sequence of two or more amino acid residues;
• Q is C or N;
• R5 is selected from the group consisting of H, an alkyl group, heteroalkyl group, alkenyl group, heteroalkenyl group, alkynyl group or a heteroalkynyl group, and is bound to Q or may form a ring together with Q and N, or R5 is absent;
• R6 is selected from the group consisting of H, an alkyl group, heteroalkyl group, alkenyl group, heteroalkenyl group, alkynyl group, heteroalkynyl group, alkoxy group, aryl group, and heteroaryl group, or is absent;
• and
• R7 is selected from the group consisting of H, an amino acid side chain, an alkyl group, heteroalkyl group, alkenyl group, heteroalkenyl group, alkynyl group, heteroalkynyl group, alkoxy group, aryl group or a heteroaryl group;
• with the proviso that when P2 is absent, P1 and P3 are not bonded to each other;
• with the proviso that when Q is N, R5 is absent, and
• with the proviso that when R5 forms a ring together with Q and N, R6 is absent.