Platinum‐Group Chelate Complexes with 9‐Hydroxyphenalenone Derivatives: Synthesis, Structures, Spectroscopic Properties and Cytotoxic Activities

Abstract

The following platinum‐group chelate complexes with 5‐R‐9‐hydroxyphenalenone (L1: R = H; L2: R = Me; L3: R = Pr) have been prepared: [RhI(L)(CO)2] (1a: L = L1; 1b: L = L2; 1c: L = L3), [PdII(L)2] (2a: L = L2; 2b: L = L3), [PtII(L1)(NH3)2](NO3) (3), and (Bu4N)[PtII(L1)(Cl)2] (4). Compounds 1a and 1b are different colors in the solid state: yellow and deep red, respectively. X‐ray analysis revealed that 1a has a regular π–π stacking structure while 1b has a dimer‐like arrangement with a RhI–RhI distance of 3.2336(6) Å. Both solids were luminescent at 77 K. Compounds 2a and 2b are planar extended π‐conjugated complexes, which exhibit two‐dimensional stacking modes in the crystal. The solid‐state structure of complex 3 is hydrogen‐bonded in a polar arrangement. The cytotoxic activities of 1a, 3, and 4, evaluated in vitro against HL60 human acute myeloid leukemia cell lines, were comparable to that of cisplatin. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

FeIII, CuII and ZnII Complexes of the Rigid 9-Oxido-phenalenone Ligand—Spectroscopy, Electrochemistry, and Cytotoxic Properties

“…The absorption spectra of Hopo exhibits absorptions in the range of 300 to 450 nm attributed to π−π* transitions ( Table 2 ) [ 26 , 27 , 29 , 35 , 50 , 52 ]. For the Zn complex, most of the absorption maxima were almost identical to those of Hopo in keeping with the very similar electrochemical properties ( Figure S7 in the Supplementary Materials ).…”

“…In a benchmarking study of the opo complexes of Rh I , Pd II and Pt II , their cytotoxic activities against HL60 human acute myeloid leukemia cell lines were reported in 2006 to be comparable to that of cisplatin [ 29 ]. After that, the opo Pt II complex [Pt(opo)(NH 3 ) 2 ] + was studied through DFT calculations alongside other Pt II -containing complexes with anti-cancer activities [ 30 ], and very recently [Pt(opo)(dach)](NO 3 ) (dach = 1,2-diaminocyclohexane) was found to have high antiproliferative activity in a murine NSCLC (lung cancer) tumour model [ 31 ].…”

In vitro activity of 1H-phenalen-1-one derivatives against Leishmania spp. and evidence of programmed cell death

“…In the absence of an effective vaccine, there is an urgent need for new and more effective drugs to replace or supplement those in current use. Natural and synthetic 1H-phenalen-1-one (PH) containing compounds exhibit a diverse range of biological activities, antifungal [8–12], antiprotozoal [10, 13–15], bactericidal [16] and cytotoxic activity against human cancer cells [17]. The active 1H-phenalen-1-one analogs were evaluated against Leishmania spp.…”

5‐(Hetero)aryl‐Substituted 9‐Hydroxyphenalenones: Synthesis and Electronic Properties of Multifunctional Donor–Acceptor Conjugates

“…But, to the best of our knowledge, the functionalization in the 5‐position of the 9‐hydroxyphenalenone has remained quite rare with the exception of two reports . On one hand methyl and propyl derivatives of palladium and rhodium complexes were investigated and in the other publication a trifunctional 1,9‐dithiophenalenylium salt was synthesized and its neutral radical was studied. An alkyl protected 5,5′,5′′‐(1,3,5‐phenylene)tris[9‐(2‐ethylhexoxy)‐1‐oxophenalene] was obtained as an intermediate product .…”

“…Interestingly, some complexes can be employed as catalysts, neutral radical conductors, and a europium complex embedded in mesoporous silica shows pronounced daylight‐excited luminescence . But, to the best of our knowledge, the functionalization in the 5‐position of the 9‐hydroxyphenalenone has remained quite rare with the exception of two reports . On one hand methyl and propyl derivatives of palladium and rhodium complexes were investigated and in the other publication a trifunctional 1,9‐dithiophenalenylium salt was synthesized and its neutral radical was studied.…”