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

Vladislava V Matveevskaya; Dmitry I Pavlov; Taisiya S Sukhikh; Artem L Gushchin; Alexander Yu Ivanov; Tatiana B Tennikova; Vladimir V Sharoyko; Sergey V Baykov; Enrico Benassi; Andrei S Potapov

doi:10.1021/acsomega.0c01204

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

ACS Omega. 2020 May 7;5(19):11167-11179. doi: 10.1021/acsomega.0c01204. eCollection 2020 May 19.

Authors

Affiliations

¹ Kizhner Research Center, National Research Tomsk Polytechnic University, 30 Lenin Avenue, 634050 Tomsk, Russia.
² Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 Lavrentiev Avenue, 630090 Novosibirsk, Russia.
³ Department of Natural Sciences, Novosibirsk State University, 1 Pirogov Street, 630090 Novosibirsk, Russia.
⁴ Center for Magnetic Resonance, Saint Petersburg State University, 26 Universitetskii Avenue, 198504 Peterhof, Russia.
⁵ Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Avenue, 198504 Peterhof, Russia.
⁶ Department of Chemistry, Shihezi University, 280N 4th Road, 832000 Shihezi, Xinjiang, PR China.

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.