Functionalized gold carbene napthaquinone complexes for use in the treatment of cancer

A compound of the formula:

• wherein:
• M is an Au or Ag ion;
• R1 and R2 are each independently alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤18), aralkyl(C≤18), or a substituted version of any of these groups;
• or —(CRaRb)C(O)Y1;
• wherein:
• Y1 is amino, hydroxy, alkoxy(C≤8), substituted alkoxy(C≤8), alkylamino(C≤8), substituted alkylamino(C≤8), dialkylamino(C≤8), or substituted dialkylamino(C≤8), and
• Ra and Rb are each independently the side chain of a canonical amino acid or alkyl(C≤8), cycloalkyl(C≤8), aryl(C≤12), aralkyl(C≤12), heteroaryl(C≤12), heteroaralkyl(C≤12), or a substituted version of these six groups;
• or
• a group of the formula:
• —((CH2)qO)nRc, wherein:
• q is 1, 2, or 3;
• n is 1-10;
• and
• Rc is hydrogen, alkyl(C≤8), or substituted alkyl(C≤8), or
• a group of the formula:
• —Y2A—R7A, wherein:
• Y2A is alkanediyl(C≤12), alkenediyl(C≤12), arenediyl(C≤18), heteroarenediyl(C≤18), or a substituted version thereof;
• and
• R7A is amino, carboxy, halo, hydroxy, mercapto, alkoxy(C≤8), substituted alkoxy(C≤8), alkylamino(C≤8), substituted alkylamino(C≤8), dialkylamino(C≤8), or substituted dialkylamino(C≤8), or —X2AC(O)R7A′;
• wherein:
• X2A is a covalent bond, NRg, or O, wherein:
• Rg is hydrogen, alkyl(C≤6), or substituted alkyl(C≤6);
• R7A′ is hydrazine, alkylhydrazine(C≤12), substituted alkylhydrazine(C≤12), heterocycloalkyl(C≤12), substituted heterocycloalkyl(C≤12), alkoxy(C≤8), substituted alkoxy(C≤8), cycloalkoxy(C≤8), substituted cycloalkoxy(C≤8), aryloxy(C≤8), substituted aryloxy(C≤8), aralkoxy(C≤8), substituted aralkoxy(C≤8), alkylamino(C≤8), substituted alkylamino(C≤8), dialkylamino(C≤8), substituted dialkylamino(C≤8), cycloalkylamino(C≤8), substituted cycloalkylamino(C≤8), arylamino(C≤8), substituted arylamino(C≤8), (alkyl)alkylamino(C≤8), substituted (alkyl)arylamino(C≤8), aralkylamino(C≤8), or substituted aralkylamino(C≤8);
• R3 is hydrogen, amino, cyano, halo, hydroxy, nitro, thio, or alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤12), heteroaryl(C≤12), aralkyl(C≤12), heteroaralkyl(C≤12), acyl(C≤12), alkoxy(C≤12), alkylamino(C≤12), dialkylamino(C≤12), or a substituted version of any of these ten groups, or —(O(CH2)r)yZ1, wherein:
• r is 1, 2, or 3;
• y is 0-10;
• and
• Z1 is hydroxy, alkoxy(C≤6), or substituted alkoxy(C≤6);
• or two or more positions are substituted with R3 and two of the R3 groups are taken together and are alkanediyl(C≤12), alkenediyl(C≤12), arenediyl(C≤18), heteroarenediyl(C≤18), or a substituted version thereof;
• R4 and R5 are each independently alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤18), aralkyl(C≤18), or a substituted version of any of these groups;
• or —(CRdRe)C(O)Y2B;
• wherein:
• Y2B is amino, hydroxy, alkoxy(C≤8), substituted alkoxy(C≤8), alkylamino(C≤8), substituted alkylamino(C≤8), dialkylamino(C≤8), or substituted dialkylamino(C≤8), and
• Rd and Re are each independently the side chain of a canonical amino acid or alkyl(C≤8), cycloalkyl(C≤8), aryl(C≤12), aralkyl(C≤12), heteroaryl(C≤12), heteroaralkyl(C≤12), or a substituted version of these six groups;
• a group of the formula:
• —((CH2)sO)pRf, wherein:
• s is 1, 2, or 3;
• p is 1-10;
• or
• Rf is hydrogen, alkyl(C≤8), or substituted alkyl(C≤8), or
• a group of the formula:
• —Y2C—R7C, wherein:
• Y2C is alkanediyl(C≤12), alkenediyl(C≤12), arenediyl(C≤18), heteroarenediyl(C≤18), or a substituted version thereof;
• and
• R7C is amino, carboxy, halo, hydroxy, mercapto, alkoxy(C≤8), substituted alkoxy(C≤8), alkylamino(C≤8), substituted alkylamino(C≤8), dialkylamino(C≤8), or substituted dialkylamino(C≤8), or —C(O)R7C′;
• wherein:
• R7C′ is alkoxy(C≤8), substituted alkoxy(C≤8), alkylamino(C≤8), substituted alkylamino(C≤8), dialkylamino(C≤8), or substituted dialkylamino(C≤8);
• R6 and R6′ are each independently hydrogen, amino, cyano, halo, hydroxy, nitro, thio, or alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤12), heteroaryl(C≤12), aralkyl(C≤12), heteroaralkyl(C≤12), acyl(C≤12), alkoxy(C≤12), alkylamino(C≤12), dialkylamino(C≤12), or a substituted version of any of these ten groups, or —(O(CH2)t)zZ2, wherein:
• t is 1, 2, or 3;
• z is 0-10;
• and
• Z2 is hydroxy, alkoxy(C≤6), or substituted alkoxy(C≤6);
• or
• m is 1, 2, 3, or 4;
• and
• X1 is an anionic species such that the charge on X1 balances the net charge on the complex.