TY - JOUR
T1 - Neutral and cationic half-sandwich arene d6 metal complexes containing pyridyl and pyrimidyl thiourea ligands with interesting bonding modes
T2 - Synthesis, structural and anti-cancer studies
AU - Adhikari, Sanjay
AU - Hussain, Omar
AU - Phillips, Roger M.
AU - Kaminsky, Werner
AU - Kollipara, Mohan Rao
PY - 2018/9/1
Y1 - 2018/9/1
N2 - The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) with benzoyl (2-pyrimidyl) thiourea (L1) and benzoyl (4-picolyl) thiourea (L2) led to the formation of cationic complexes bearing formula [(arene) M (L1)к2
(N,S)Cl]+ and [(arene) M (L2)к2
(N,S)Cl]+ [(arene) = p-cymene, M = Ru, (1, 4); Cp*, M = Rh (2, 5) and Ir (3, 6)]. Precursor compounds reacted with benzoyl (6-picolyl) thiourea (L3) affording neutral complexes having formula [(arene) M (L3)к1
(S)Cl2] [arene = p-cymene, M = Ru, (7); Cp*, M = Rh (8), Ir (9)]. X-ray studies revealed that the methyl substituent attached to the pyridine ring in ligands L2 and L3 affects its coordination mode. When methyl group is at the para position of the pyridine ring (L2), the ligand coordinated metal in a bidentate chelating N, S- mode whereas methyl group at ortho position (L3), it coordinated in a monodentate mode. Further the anti-cancer studies of the thiourea derivatives and its complexes carried out against HCT-116, HT-29 (human colorectal cancer), Mia-PaCa-2 (human pancreatic cancer) and ARPE-19 (non-cancer retinal epithelium) cell lines showed that the thiourea ligands are inactive but upon complexation, the metal compounds displayed potent and selective activity against cancer cells in vitro. Iridium complexes were found to be more potent as compared to ruthenium and rhodium complexes.
AB - The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) with benzoyl (2-pyrimidyl) thiourea (L1) and benzoyl (4-picolyl) thiourea (L2) led to the formation of cationic complexes bearing formula [(arene) M (L1)к2
(N,S)Cl]+ and [(arene) M (L2)к2
(N,S)Cl]+ [(arene) = p-cymene, M = Ru, (1, 4); Cp*, M = Rh (2, 5) and Ir (3, 6)]. Precursor compounds reacted with benzoyl (6-picolyl) thiourea (L3) affording neutral complexes having formula [(arene) M (L3)к1
(S)Cl2] [arene = p-cymene, M = Ru, (7); Cp*, M = Rh (8), Ir (9)]. X-ray studies revealed that the methyl substituent attached to the pyridine ring in ligands L2 and L3 affects its coordination mode. When methyl group is at the para position of the pyridine ring (L2), the ligand coordinated metal in a bidentate chelating N, S- mode whereas methyl group at ortho position (L3), it coordinated in a monodentate mode. Further the anti-cancer studies of the thiourea derivatives and its complexes carried out against HCT-116, HT-29 (human colorectal cancer), Mia-PaCa-2 (human pancreatic cancer) and ARPE-19 (non-cancer retinal epithelium) cell lines showed that the thiourea ligands are inactive but upon complexation, the metal compounds displayed potent and selective activity against cancer cells in vitro. Iridium complexes were found to be more potent as compared to ruthenium and rhodium complexes.
KW - cytotoxicity
KW - iridium
KW - rhodium
KW - ruthenium
KW - thiourea
UR - http://www.scopus.com/inward/record.url?scp=85051481344&partnerID=8YFLogxK
U2 - 10.1002/aoc.4476
DO - 10.1002/aoc.4476
M3 - Article
AN - SCOPUS:85051481344
VL - 32
JO - Applied Organometallic Chemistry
JF - Applied Organometallic Chemistry
SN - 0268-2605
IS - 9
M1 - e4476
ER -
