Integrin targeting ligands and uses thereof

A compound of Formula Ip:

• or a pharmaceutically acceptable salt thereof, wherein
• R1 is optionally substituted alkyl, optionally substituted alkoxy, or
• wherein R11 and R12 are each independently optionally substituted alkyl or a linking moiety, or R1 is a linking moiety;
• R2 is H, optionally substituted alkyl, or a moiety;
• R3 is H or optionally substituted alkyl;
• R4 is H or optionally substituted alkyl;
• R5 is H or optionally substituted alkyl;
• R6 is selected from the group consisting of H, optionally substituted alkyl, optionally substituted alkoxy, halo, optionally substituted amino, or a linking moiety;
• Q is optionally substituted aryl or optionally substituted alkylene;
• X is O, CR8R9, NR8;
• wherein R8 is selected from H, optionally substituted alkyl, or R8 is taken together with Rx or Ry to form a 4-, 5-, 6-, 7-, 8- or 9-membered ring, and R9 is H or optionally substituted alkyl;
• Rx and Ry are each independently H, optionally substituted alkyl, a cargo molecule or Rx and Ry may be taken together to form a double bond with R10, wherein R10 is H, optionally substituted alkyl, or R10 may be taken together with X and the atoms to which it is attached to form a 4-, 5-, 6-, 7-, 8, or 9-membered ring;
• wherein at least one of R1, R2, R6, R11, R12, Rx and Ry comprise a linking moiety;
• and
• wherein when Q is optionally substituted alkyl and the length of the optionally substituted alkyl chain represented by Q is 3 carbons, then R1 is

A method of making a compound of Formula I

• or a pharmaceutically acceptable salt thereof, wherein
• R1 is optionally substituted alkyl, optionally substituted alkoxy, or
• wherein R11 and R12 are each independently optionally substituted alkyl or a cargo molecule, or R1 is a cargo molecule;
• R2 is H, optionally substituted alkyl, or a cargo molecule;
• R3 is H or optionally substituted alkyl;
• R4 is H or optionally substituted alkyl;
• R5 is H or optionally substituted alkyl;
• R6 is selected from the group consisting of H, optionally substituted alkyl, optionally substituted alkoxy, halo, optionally substituted amino, or a cargo molecule;
• Q is optionally substituted aryl or optionally substituted alkylene;
• X is O, CR8R9, NR8;
• wherein R8 is selected from H, optionally substituted alkyl, or R8 is taken together with Rx or Ry to form a 4-, 5-, 6-, 7-, 8- or 9-membered ring, and R9 is H or optionally substituted alkyl;
• Rx and Ry are each independently H, optionally substituted alkyl, a cargo molecule or Rx and Ry may be taken together to form a double bond with R10, wherein R10 is H, optionally substituted alkyl, or R10 may be taken together with X and the atoms to which it is attached to form a 4-, 5-, 6-, 7-, 8, or 9-membered ring;
• wherein at least one of R1, R2, R6, R11, R12, Rx and Ry comprise a cargo molecule;
• and
• wherein when Q is optionally substituted alkyl and the length of the optionally substituted alkyl chain represented by Q is 3 carbons, then R1 is
• comprising reacting a compound of Formula Ip
• or a pharmaceutically acceptable salt thereof, wherein
• R1 is optionally substituted alkyl, optionally substituted alkoxy, or
• wherein R11 and R12 are each independently optionally substituted alkyl or a linking moiety, or R1 is a linking moiety;
• R2 is H, optionally substituted alkyl, or a linking moiety;
• R3 is H or optionally substituted alkyl;
• R4 is H or optionally substituted alkyl;
• R5 is H or optionally substituted alkyl;
• R6 is selected from the group consisting of H, optionally substituted alkyl, optionally substituted alkoxy, halo, optionally substituted amino, or a linking moiety;
• Q is optionally substituted aryl or optionally substituted alkylene;
• X is O, CR8R9, NR8;
• wherein R8 is selected from H, optionally substituted alkyl, or R8 is taken together with Rx or Ry to form a 4-, 5-, 6-, 7-, 8- or 9-membered ring, and R9 is H or optionally substituted alkyl;
• Rx and Ry are each independently H, optionally substituted alkyl, a cargo molecule or Rx and Ry may be taken together to form a double bond with R10, wherein R10 is H, optionally substituted alkyl, or R10 may be taken together with X and the atoms to which it is attached to form a 4-, 5-, 6-, 7-, 8, or 9-membered ring;
• wherein at least one of R1, R2, R6, R11, R12, Rx and Ry comprise a linking moiety;
• and
• wherein when Q is optionally substituted alkyl and the length of the optionally substituted alkyl chain represented by Q is 3 carbons, then R1 is
• with a cargo molecule comprising a reactive moiety.