CHEMICAL AND BIOLOGICAL STUDIES OF DICHLORO(2-((DIMETHYLAMINO)METHYL)PHENYL)GOLD(III)

Several new organogold(III) derivatives of the type [AuX(2)(damp)] (da mp = o-C(6)H(4)CH(2)NMe(2)) have been prepared [X = CN, SCN, dtc, or X (2) = tm; dtc = R(2)NCS(2) (R = Me (dmtc) or Et (detc)); tm = SCH(CO2) CH2CO2Na] together with [AuCl(tpca)(damp)]Cl (tpca = o-Ph(2)PC(6)H(4)C O(2)H), [Au(dtc)(damp)]Y (Y = Cl, BPh(4)) and K[Au(CN)(3)(damp)]. The C-13 NMR spectra of these and previous derivatives have been fully ass igned. In [Au(dtc)(2)-(damp)] and K[Au(CN)(3)(damp)], the damp ligand is coordinated only through carbon, as shown by X-ray crystallography and/or NMR. [Au(detc)(2)(damp)] has space group C2/c, with a = 29.884( 4) Angstrom, b = 13.446(2) Angstrom, c = 12.401(2) Angstrom, beta = 99 .45(3)degrees, V = 4915 Angstrom(3), Z = 8, and R = 0.057 for 1918 ref lections. The damp and one detc ligand are monodentate, the other detc is bidentate; in solution, the complex shows dynamic behavior, with t he detc ligands appearing equivalent. The crystal structure of [Au(dmt c)(damp)]BPh(4) [Pna2(1), a = 26.149(5) Angstrom, b = 11.250(2) Angstr om, c = 11.921(2) Angstrom, V = 3507 Angstrom(3), Z = 4, R = 0.073, 17 72 reflections] shows both ligands to be bidentate in the cation, but the two Au-S distances are nonequivalent. The crystal structure of [Au (tm)(damp)] has also been determined [P2(1)/n, a = 18.267(7) Angstrom, b = 9.618(3) Angstrom, c = 18.938(4) Angstrom, beta = 113.45(3)degree s, V = 3053 Angstrom(3), Z = 8, R = 0.079, 1389 reflections]. The tm i s bound through sulfur and the carboxyl group which allows five-member ed ring formation. In all three structures, the trans-influence of the sigma-bonded aryl group is apparent. [AuCl2(damp)] has been tested in vitro against a range of microbial strains and several human tumor li nes, where it displays differential cytotoxicity similar to that of ci splatin. Against the ZR-75-1 human tumor xenograft, both [AuCl2(damp)] and cisplatin showed limited activity.