Substantially cell membrane impermeable compound and use thereof

A compound according to Formula (I) or a salt thereof:

• A-[(XBX′)nB′—Y]p (I)
• wherein
• A is selected from the group consisting of glutathione, glucosamine, cysteinylglycine, cysteic acid, aspartic acid, glutamic acid, lysine, and arginine, and wherein the sulfur atom of each sulfur containing compound is optionally a sulfoxide or sulfone;
• X is selected from NR—, S(O)—, —S(O)O—, —S(O)2—, —S(O)2O—, —C(O)—, —C(S)—, —C(O)O—, C(S)O—, —C(S)S—, —P(O)(R1)—, —P(O)(R1)O—, or is absent;
• B is selected from C1–C10 alkylene, C2–C10 alkenylene, C2–C10 alkynylene, C3–C10 cycloalkylene, C5–C10 cycloalkenylene, C3–C10 heterocycloalkylene, C5–C10 heterocycloalkenylene, C6–C12 arylene, heteroarylene or C2–C10 acyl;
• X′ is selected from NR—, —O—, —S—, —Se—, —S—S—, S(O)—, —OS(O)—, OS(O)O—, —OS(O)2, —OS(O)2O—, —S(O)O—, —S(O)2—, —S(O)2O—, —OP(O)(R1)—, —OP(O)(R1)O—, —OP(O)(R1)OP(O)(R1)O—, —C(O)—, —C(S)—, —C(O)O—, C(S)O—, —C(S)S—, —P(O)(R1)—, —P(O)(R1)O—,
• or is absent;
• wherein E is O, S, Se, NR or N(R)2+;
• and
• B′ is selected from C1–C10 alkylene, C2–C10 alkenylene, C2–C10 alkynylene, C3–C10 cycloalkylene, C5–C10 cycloalkenylene, C3–C10 heterocycloalkylene, C5–C10 heterocycloalkenylene, C6–C12 arylene, and heteroarylene, or is absent;
• wherein
• each R is independently selected from hydrogen, C1–C10 alkyl, C2–C10 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, OR2 or C2–C10 acyl;
• R′ is the same as R or two R′ are taken together with the nitrogen atoms to which they are attached to form a 5 or 6-membered saturated or unsaturated heterocyclic ring;
• each R1 is independently selected from hydrogen, C1–C10 alkyl, C2–C10 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C3–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, halo, OR2 or N(R)2;
• each R2 is independently selected from hydrogen, C1–C10 alkyl, C2–C10 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl or —C(O)R5;
• each R5 is independently selected from hydrogen, C1–C10 alkyl, C2–C10 4 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, C1–C10 alkoxy, C3–C10 alkenyloxy, C3–C10 alkynyloxy, C3–C10 cycloalkyloxy, C5–C10 cycloalkenyloxy, C3–C10 heterocycloalkyloxy, C5–C10 heterocycloalkenyloxy, C6–C12 aryloxy, heteroaryloxy, C1–C10 alkylthio, C3–C10 alkenylthio, C3–C10 alkynylthio, C3–C10 cycloalkylthio, C5–C10 cycloalkenylthio, C3–C10 heterocycloalkylthio, C5–C10 heterocycloalkenylthio, C6–C12 arylthio, heteroarylthio, OH, SH or N(R)2;
• wherein for each instance that B and/or B′ is arylene, the substituents directly attached to the respective arylene rings are in a para, meta or ortho relationship, and
• wherein each alkylene, alkenylene, alkynylene, cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene and acyl are optionally independently substituted with hydrogen, C1–C10 alkyl, C2–C10 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, halo, cyano, cyanate, isocyanate, OR2a, SR6, nitro, arsenoxide, —S(O)R3, —OS(O)R3, —S(O)2R3, —OS(O)2R3, —P(O)R4R4, —OP(O)R4R4, —N(R″)2, —NRC(O)(CH2)mQ, —C(O)R5,
• wherein R, R1 and R5 are as defined above;
• and
• R2a is selected from hydrogen, C1–C10 alkyl, C2–C5 alkenyl, C2–C5 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C6–C12 aryl, —S(O)R3, —S(O)2R3, —P(O)(R4)2, N(R)2 or —C(O)R5;
• each R3 is independently selected from hydrogen, C1–C10 alkyl, C2–C10 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, C1–C10 alkoxy, C3–C10 alkenyloxy, C3–C10 alkynyloxy, C3–C10 cycloalkyloxy, C5–C10 cycloalkenyloxy, C3–C10 heterocycloalkyloxy, C5–C10 heterocycloalkenyloxy, C6–C12 aryloxy, heteroaryloxy, C1–C10 alkylthio, C3–C10 alkenylthio, C3–C10 alkynylthio, C3–C10 cycloalkylthio, C5–C10 cycloalkenylthio, C3–C10 heterocycloalkylthio, C5–C10 heterocycloalkenylthio, C6–C12 arylthio, heteroarylthio or N(R)2;
• each R4 is independently selected from hydrogen, C1–C10 alkyl, C2–C10 alkenyl, C2–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, C1–C10 alkoxy, C3–C10 alkenyloxy, C3–C10 alkynyloxy, C3–C10 cycloalkyloxy, C5–C10 cycloalkenyloxy, C3–C10 heterocycloalkyloxy C5–C10 heterocycloalkenyloxy, C6–C12 aryloxy, heteroaryloxy, C1–C10 alkylthio, C3–C10 alkenylthio, C3–C10 alkynylthio, C3–C10 cycloalkylthio, C5–C10 cycloalkenylthio, C3–C10 heterocycloalkylthio, C3–C10 heterocycloalkenylthio, C6–C12 arylthio, heteroarylthio, halo or N(R)2;
• R6 is selected from C1–C10 alkyl, C2–C10 alkenyl, C3–C10 alkynyl, C3–C10 cycloalkyl, C5–C10 cycloalkenyl, C3–C10 heterocycloalkyl, C5–C10 heterocycloalkenyl, C6–C12 aryl, heteroaryl, C1–C10 alkylthio, C3–C10 alkenylthio, C3–C10 alkynylthio, C3–C10 cycloalkylthio, C5–C10 cycloalkenylthio, C3–C10 heterocycloalkylthio, C5–C10 heterocycloalkenylthio, C6–C12 arylthio, heteroarylthio, —S(O)R3, —S(O)2R3 or —C(O)R5,
• R″ is the same as R or two R″ taken together with the N atom to which they are attached may form a saturated, unsaturated or aromatic heterocyclic ring system;
• Q is selected from halogen and —OS(O)2Q1;
• wherein Q1 is selected from C1–C4 alkyl, C1–C4 perfluoroalkyl, phenyl, p-methylphenyl;
• m is an integer selected from 1 to 5,
• Y comprises at least one arsenoxide group;
• p is an integer selected from 1 to 10;
• n is an integer selected from 0 to 20, and
• wherein the sum total of carbon atoms in A and (XBX′)nB′ together, is greater than 6.