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Synthesis, structural and chemosensitivity studies of arene d 6 metal complexes having N‐phenyl‐N´‐(pyridyl/pyrimidyl)thiourea derivatives
Author(s) -
Adhikari Sanjay,
Hussain Omar,
Phillips Roger M.,
Kaminsky Werner,
Kollipara Mohan Rao
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4362
Subject(s) - chemistry , thiourea , denticity , ruthenium , ligand (biochemistry) , cytotoxicity , chelation , cationic polymerization , medicinal chemistry , metal , stereochemistry , iridium , bromide , cisplatin , in vitro , polymer chemistry , inorganic chemistry , organic chemistry , receptor , medicine , biochemistry , surgery , chemotherapy , catalysis
The d 6 metal complexes of thiourea derivatives were synthesized to investigate its cytotoxicity. Treatment of various N‐phenyl‐N´ pyridyl/pyrimidyl thiourea ligands with half‐sandwich d 6 metal precursors yielded a series of cationic complexes. Reactions of ligand (L1‐L3) with [( p ‐cymene)RuCl 2 ] 2 and [Cp*MCl 2 ] 2 (M = Rh/Ir) led to the formation of a series of cationic complexes bearing general formula [(arene)M(L1)к 2 ( N,S ) Cl] + , [(arene)M(L2)к 2 ( N,S ) Cl] + and [(arene)M(L3)к 2 ( N,S ) Cl] + [arene = p ‐cymene, M = Ru ( 1 , 4 , 7 ); Cp*, M = Rh ( 2 , 5 , 8 ); Cp*, Ir ( 3 , 6 , 9 )]. These compounds were isolated as their chloride salts. X‐ray crystallographic studies of the complexes revealed the coordination of the ligands to the metal in a bidentate chelating N,S‐ manner. Further the cytotoxicity studies of the thiourea derivatives and its complexes evaluated against HCT‐116 (human colorectal cancer), MIA‐PaCa‐2 (human pancreatic cancer) and ARPE‐19 (non‐cancer retinal epithelium) cancer cell lines showed that the thiourea ligands displayed no activity. Upon complexation however, the metal compounds possesses cytotoxicity and whilst potency is less than cisplatin, several complexes exhibited greater selectivity for HCT‐116 or MIA‐PaCa‐2 cells compared to ARPE‐19 cells than cisplatin in vitro . Rhodium complexes of thiourea derivatives were found to be more potent as compared to ruthenium and iridium complexes.