Selenoquinones Stabilized by Ruthenium(II) Arene Complexes: Synthesis, Structure, and Cytotoxicity

• Published in: Chemistry : a European journal 2014-05, Vol.20 (19), p.5795-5801
• Main Authors: Dubarle-Offner , Julien, Clavel, Catherine M., Gontard , Geoffrey, Dyson, Paul J., Amouri , Hani
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Aromatic compounds; Cancer; Cell Line, Tumor; Chemical Sciences; Chemistry; Coordination Complexes - chemical synthesis; Coordination Complexes - chemistry; Crystal structure; Crystallography, X-Ray; cytotoxicity; Cytotoxins - chemistry; Female; Human; Humans; Magnetic Resonance Spectroscopy; Medical research; Metalorganic compounds; Molecular Structure; Ovarian cancer; Ovarian Neoplasms - drug therapy; pi interactions; Quinones - chemical synthesis; Quinones - chemistry; Ruthenium; Ruthenium - chemistry; sandwich complexes; selenoquinones; Synthesis; X-rays
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201304991

A new series of monoselenoquinone and diselenoquinone π complexes, [(η6‐p‐cymene)Ru(η4‐C6R4SeE)] (R=H, E=Se (6); R=CH3, E=Se (7); R=H, E=O (8)), as well as selenolate π complexes [(η6‐p‐cymene)Ru(η5‐C6H3R2Se)][SbF6] (R=H (9); R=CH3 (10)), stabilized by arene ruthenium moieties were prepared in good yields through nucleophilic substitution reactions from dichlorinated‐arene and hydroxymonochlorinated‐arene ruthenium complexes [(η6‐p‐cymene)Ru(C6R4XCl)][SbF6]2 (R=H, X=Cl (1); R=CH3, X=Cl (2); R=H, X=OH (3)) as well as the monochlorinated π complexes [(η6‐p‐cymene)Ru(η5‐C6H3R2Cl)][SbF6]2 (R=H (4); R=CH3 (5)). The X‐ray crystallographic structures of two of the compounds, [(η6‐p‐cymene)Ru(η4‐C6Me4Se2)] (7) and [(η6‐p‐cymene)Ru(η4‐C6H4SeO)] (8), were determined. The structures confirm the identity of the target compounds and ascertain the coordination mode of these unprecedented ruthenium π complexes of selenoquinones. Furthermore, these new compounds display relevant cytotoxic properties towards human ovarian cancer cells. All in the family: A series of organometallic ruthenium complexes stabilize selenolate, monoselenoquinone, and diselenobenzoquinone entities through π‐bonding interactions to a (p‐cymene)RuII moiety (see figure). The complexes display moderate cytotoxic properties towards human ovarian cancer cells.