Arene–Ruthenium(II) Complexes Containing 11H-Indeno[1,2-b]quinoxalin-11-one Derivatives and Tryptanthrin-6-oxime: Synthesis, Characterization, Cytotoxicity, and Catalytic Transfer Hydrogenation of Aryl Ketones

Abstract

A series of novel mono- and binuclear arene–ruthenium­(II) complexes [(p-cym)­Ru­(L)­Cl] containing 11H-indeno­[1,2-b]­quinoxalin-11-one derivatives or tryptanthrin-6-oxime were synthesized and characterized by X-ray crystallography, IR, NMR spectroscopy, cyclic voltammetry, and elemental analysis. Theoretical calculations invoking singlet state geometry optimization, solvation effects, and noncovalent interactions were done using density functional theory (DFT). DFT calculations were also applied to evaluate the electronic properties, and time-dependent DFT was applied to clarify experimental UV–vis results. Cytotoxicity for cancerous and noncancerous human cell lines was evaluated with cell viability MTT assay. Complexes demonstrated a moderate cytotoxic effect toward cancerous human cell line PANC-1. The catalytic activity of the complexes was evaluated in transfer hydrogenation of aryl ketones. All complexes exhibited good catalytic activity and functional group tolerance.

Carboxamide carbonyl-ruthenium(ii) complexes: detailed structural and mechanistic studies in the transfer hydrogenation of ketones

“…In comparison to literature reports, the catalytic activities achieved by Ru1-Ru4 fall within the range of other related Ru(II)-PPh 3 complexes of TOF up to 1.0 Â 10 2 h À1 . [49][50][51][52][53][54][55][56][57] However, the catalytic activities of complexes Ru1-Ru4 are lower compared to some of the highly active ruthenium(II) complexes where the TOFs between 1.0 Â 10 4 -1.0 Â 10 5 h À1 were achieved. 58-61 2.3.4 Investigation of TH reactions using different ketone substrates.…”

Ruthenium Complexes as Potential Cancer Cell Growth Inhibitors for Targeted Chemotherapy

“…This ligand is a wellcharacterized recognition area for the active site interaction of carbonic anhydrase (CA). [34,35] CAs are zinc metalloenzymes that are present in a diverse range of taxonomic taxa, including humans, plants, algae, bacteria, and microorganisms. [36] Each of the sixteen carbonic anhydrase isozymes present in mammals is subcellular located and distributed differently throughout the body.…”

“…The aromatic sulphonamide moiety is a bioactive ligand capable of forming Ru(II) arene complexes. This ligand is a well‐characterized recognition area for the active site interaction of carbonic anhydrase (CA) [34,35] . CAs are zinc metalloenzymes that are present in a diverse range of taxonomic taxa, including humans, plants, algae, bacteria, and microorganisms [36] .…”

Neuroprotective Effects of the Lithium Salt of a Novel JNK Inhibitor in an Animal Model of Cerebral Ischemia–Reperfusion

“…Since oximes, including derivatives of 11 H -indeno[1,2- b ]quinoxalin-11-ones and related tryptanthrin analogs, could form complexes with different metal ions, and the ion-chelating properties of ligands can alter to their biological activities [ 38 , 39 , 40 ], we hypothesized that other salts of IQ-1 may lead to a change in therapeutic potential of the resulting ion complexes. In particular, we evaluated lithium salts of IQ-1 because Li + is also a promising candidate for the treatment of ischemic stroke [ 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ].…”