Anticancer Ru(η6-p-cymene) complexes of 2-pyridinecarbothioamides: A structure–activity relationship study

Organoruthenium and Organoosmium Complexes of 2‐Pyridinecarbothioamides Functionalized with a Sulfonamide Motif: Synthesis, Cytotoxicity and Biomolecule Interactions

“…Therefore, we label this compound as 1d neutral .T his is in contrast to all other molecular structures of relatedR ua nd Os complexes in which the PCAl igand was neutral and ac omplex cation was formed. [25][26][27] The Os-cym centroid and Os-Cl distances were 1.671 and 2.442(4) ,r espectively,a nd therefore similar to those reported for related complexes. [25][26][27] The OsÀS1 and OsÀN1 bond lengths were 2.355(4) and 2.133(1) ,r espectively.T he C6ÀS1 bond (1.754(15) in 1d neutral )w as elongated as compared to 1.655(5) for 1,i ndicating greater single bond character.T he C6ÀN2 bond length of 1.251 (19) in 1d neutral was slightly shorter compared to ab ond length of 1.345(6) in 1, demonstrating the increased double bond character upon coordination of the Os to the Sa tom and deprotonation of the amide group.T he latter bond is hardly modified if PCA coordinates as aneutral ligand to ametal center.…”

“…This is in contrast to all other molecular structures of related Ru and Os complexes in which the PCA ligand was neutral and a complex cation was formed . The Os–cym centroid and Os–Cl distances were 1.671 and 2.442(4) Å, respectively, and therefore similar to those reported for related complexes . The Os−S1 and Os−N1 bond lengths were 2.355(4) and 2.133(1) Å, respectively.…”

“…[24] We have recently developed organometallic anticancer complexes of 2-pyridinecarbothioamide (PCA) ligands. [25][26][27][28][29] The Ru complex, termed plecstatin-1, demonstrated target selectivity for plectin in an invasive B16 melanoma tumor model. [28] Herein, we report the functionalization of the PCAs caffold with the sulfonamide pharmacophore and its coordination to Ru II /Os II -cym (cym = h 6 -p-cymene) organometallics.…”

A Multitargeted Approach: Organorhodium Anticancer Agent Based on Vorinostat as a Potent Histone Deacetylase Inhibitor

“…[19] Forcoordination of the Os center to S1 and N1, the hydrogen bond, N1•••H N2 ,in1 was broken and resulted in the PCA ligand losing its planarity (torsion angle C5-C6-N2-C7 135.088 8)a ss een in the molecular structure of 1.U pon metal coordination, the C6 À S1 bond was elongated [1.691-(6) vs.1.665 3], as observed for related compounds. [19,20] This elongation indicates higher single-bond character for C6ÀS1 and higher double-bond character for the C6ÀN2 bond.…”

“…[19] Theh igh stability of PCA-metal bonds,e ven under acidic conditions, provides as tructural scaffold suitable for oral administration. [19,20]…”