Discovery, Structure, and Anticancer Activity of an Iridium Complex of Diselenobenzoquinone

Abstract

Caught in the act: The first stable η4‐diseleno‐p‐benzoquinone complex, [Cp*Ir(η4‐C6H4Se2)], has been isolated. The X‐ray structure (see picture; Ir magenta, Se yellow) confirms the coordination of the elusive diselenobenzoquinone intermediate. The anticancer activity of this complex was compared to related oxygen and sulfur analogues; only the diseleno complex was cytotoxic, having a comparable activity to cisplatin.

Trinuclear Half‐Sandwich RuII, RhIII and IrIII Polyester Organometallic Complexes: Synthesis and in vitro Evaluation as Antitumor Agents

“…The methyl protons of the pentamethylcyclopentadienyl ligands of the rhodium ( 5 , 8 , 11 and 14 ) and iridium ( 6 , 9 , 12 and 15 ) complexes are observed as singlets in the range δ = 1.31–1.60 ppm in the 1 H NMR spectra, similarly to those observed in related structures 18–20. For the mono‐ and trimeric Ru II complexes ( 7 , 10 , 13 and 16 ), the p ‐cymene ligand displays a characteristic pattern as observed in the neutral and cationic complexes previously reported 17,19,21–24.…”

Metal-Stabilized o-Quinone Methides, Thioquinones, and Selenoquinones: Trapping Important Reactive Intermediates and Beyond

“…52 Furthermore, we investigated the anticancer activity of a family of metalated quinones, thioquinones, and selenoquinones, and remarkably the selenoquinone complex exhibited a cytotoxicity similar to that of cisplatin, suggesting a role for such selenium derivatives (see Section 4.1.2).…”

“On Water”: Efficient Iron‐Catalyzed Cycloaddition of Aziridines with Heterocumulenes

“…Firstly, the optimization of the reaction conditions was carried out by using phenyl isoselenocyanate (1 a) and 1isopropyl-2-phenylaziridine (2 a) as model substrates in the presence of Fe(NO 3 ) 3 ·9 H 2 O (10 mol %) and water as the solvent at various temperatures (Table 1). Gratifyingly, the reaction proceeded to afford selectively the target iminoazoselenolidine [12] 3 a after five hours in 80 % conversion at room temperature when the suspension of the soluble Fe(NO 3 ) 3 ·9 H 2 O and the insoluble substrates 1 a and 2 a in water was stirred ( Next, the scope of the procedure was studied for the reactions of the substituted isoselenocyanates ( Table 2). A series of substrates 1 a-l having both the electron-withdrawing and -donating groups on the phenyl ring readily reacted with aziridine 2 a to give the target products in one hour with good to high yields.…”

“…A series of substrates 1 a-l having both the electron-withdrawing and -donating groups on the phenyl ring readily reacted with aziridine 2 a to give the target products in one hour with good to high yields. [12] For example, aryl isoselenocyanates containing 2-methoxy, 3-methyl, 4-chloro, 4-iodo, 4-methoxy, 4methyl, and 4-nitro substituents on the phenyl ring reacted to the target products 3 b-h in 61-90 % yield. Recrystallization of 3 b in hexane gave crystals, the structure of which was confirmed by single-crystal X-ray analysis (Figure 1).…”