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Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour
Author(s) -
Biancalana Lorenzo,
Abdalghani Issam,
Chiellini Federica,
Zacchini Stefano,
Pampaloni Guido,
Crucianelli Marcello,
Marchetti Fabio
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201800284
Subject(s) - chemistry , ruthenium , acetophenone , catalysis , transfer hydrogenation , sodium formate , medicinal chemistry , stereochemistry , organic chemistry
The Ru II arene complexes [Ru(η 6 ‐ p ‐cymene)(κ 2 N,O ‐aa)Cl] (aa = l‐ glutaminato, 1 ; l‐ homoserinato, 2 ; l‐ tyrosinato, 3 ; l‐ serinato, 4 ; l‐ prolinato, 5 ; trans ‐4‐hydroxyl‐ l‐ prolinato, 6 ; l‐ threoninato, 7 ; glycinato, 8 ) were synthesized in high yields by the reactions of [Ru(η 6 ‐ p ‐cymene)Cl 2 ] 2 with aa/MOH (M = Na, K). The salt [Ru(η 6 ‐ p ‐cymene)(κ 2 N,O ‐ l ‐serinato)(PPh 3 )][CF 3 SO 3 ], 9 [CF 3 SO 3 ], was prepared in 68 % yield from 4 and AgSO 3 CF 3 /PPh 3 . All the products were fully characterized by analytical and spectroscopic methods, moreover the X‐ray structures of 1 and 2 were elucidated by X‐ray diffraction. Compounds 1 – 7 and 9 [CF 3 SO 3 ] were studied as catalytic precursors for the transfer hydrogenation reaction (THR) of acetophenone, using 2‐propanol or sodium formate (in water) as hydrogen sources, under variable experimental conditions. The catalytic process was investigated also under microwave irradiation. In general, all the catalytic reactions selectively afforded 1‐phenylethanol, and the best results were achieved with 5 and 6 , in terms of both activity and enantioselectivity (enantiomeric excess up to 78 %). The in vitro cytotoxicity of 1 , 4 , 5 and 9 [CF 3 SO 3 ] was assessed towards the human pancreatic cancer cell line BxPC3 and the mouse embryo fibroblast Balb/3T3 Clone A31 cell line, all of the investigated compounds showing to be substantially inactive. The catalytic and biological results will be discussed in relation to the relevant chemical behaviour of the compounds in water solution.