Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity (original) (raw)
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2013
Two ligands: 4-hydrazinyl-1-(4-methoxyphenyl)-2,5-dihydro-1H-pyrrole-3-carbonitrile (H2L) and 4-(2(1H-pyrrol-2-yle)hydrazinyl)-1-4(4-methoxyphenyl)-2,5-dihydro-1H-pyrrol-3-carbonitrile (H2L) have been prepared and characterized. Their copper(II), nickel(II), cobalt(II), manganese(II) and zinc(II) complexes have been also synthesized and characterized by infrared, electronic spectra, magnetic and conductivity measurements in addition to elemental and thermal analyses. Octahedral structures are suggested for the H2L complexes of Cu(II) and Mn(II) and the H2L complexes of Cu(II), Ni(II) and Mn(II), whereas tetrahedral structures are proposed for the H2L complexes of Co(II) and Zn(II) and the H2L complex of Co(II). Moreover, the results showed that both ligands are tetradentate in all of their complexes. They also indicated that the complexes exhibit higher antimicrobial activity than their ligands and Mn(II) exhibits a wide range of antimicrobial activity against gram positive, gram ne...
Journal of the American Chemical Society, 2003
Supporting Information I. Preparation and NMR data of new complexes General Details. All experiments were preformed in inert atmosphere using standard gloveboxe or Schlenk line techniques. Acetonitrile, benzene, hexamethyldisiloxane and methylene chloride were dried over 4Å molecular sieves. Diethyl ether, hexanes and toluene were dried by passage through cylinders of activated alumina and 4Å molecular sieves. C 6 D 6 was dried and stored over 4Å molecular sieves. 2-iminopyrroles, 1 [(SMe 2)PtMe 2 ] 2 2 and (SMe 2) 2 Pt(Me)Cl 2 were prepared via literature methods. The lithium salts of 2-iminopyrroles were prepared by reaction with BuLi in hexanes and isolated by suction filtration in the glovebox. Complexes cis-2a-c were synthesized via the following method: [(SMe 2)PtMe 2 ] 2 and 2 molar equivalents of 2-iminopyrrole were dissolved in benzene in scintillation vials. The resulting yellow, homogenous solutions was stirred for 2-3 days at room temperature. The solvent was removed and the yellow solids were recrystallized from cold CH 2 Cl 2 solutions layered with hexamethyldisiloxane in moderate yields. Complexes trans-2a,b,d were prepared via the following method: trans-(SMe 2) 2 Pt(Me)Cl was suspended in 6 mL Et 2 O in a scintillation vial. One molar equivalent of the lithium salt of 2-1
Inorganica Chimica Acta, 2010
Platinum(II) and platinum(IV) complexes with 3-amino-5-methyl-5-(4-pyridyl)-2,4-imidazolidenedione (L) with general formulaеcis-[PtL2X2]·nH2O and [PtL2Cl4], where X=Cl−, Br−, I− and n=2–4) were synthesized. The novel compounds were fully characterized by elemental analysis, IR, 1H, 13C, 195Pt NMR spectra, thermal analysis and molar conductivity. The geometry of Pt(II) complexes and of the organic ligand in the gas phase were optimized using the hybrid DFT
New palladium (Pd)II and platinum (Pt)II complexes (C1−C5) from the Schiff base ligands, R-(phenyl)methanamine (L1), R-(pyridin-2-yl)methanamine (L2), and R-(furan-2-yl)methanamine (L3) (R-(E)-N-((1H-pyrrol-2-yl) methylene)) are herein reported. The complexes (C1−C5) were characterized by FTIR, 1 H and 13 C NMR, UV−vis, and microanalyses. Single-crystal X-ray crystallographic analysis was performed for the two ligands (L1−L2) and a Pt complex. Both L1 and L2 belong to P2 1 /n monoclinic and P-1 triclinic space systems, respectively. The complex C5 belongs to the P21/c monoclinic space group. The investigated molar conductivity of the complexes in DMSO gave the range 4.0−8.8 μS/cm, suggesting neutrality, with log P values ≥ 1.2692 ± 0.004, suggesting lipophilicity. The anticancer activity and mechanism of the complexes were investigated against various human cancerous (Caco-2, HeLa, HepG2, MCF-7, and PC-3) and noncancerous (MCF-12A) cell lines using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and Apopercentage assays, respectively. C5 demonstrated strong DNA-binding affinity for calf thymus DNA (CT-DNA) with a binding constant of 8.049 × 10 4 M −1. C3 reduced cell viability of all the six cell lines, which included five cancerous cell lines, by more than 80%. The C5 complex also demonstrated remarkably high selectivity with no cytotoxic activity toward the noncancerous breast cell line but reduced the viability of the five cancerous cell lines, which included one breast cancer cell line, by more than 60%. Further studies are required to evaluate the selective toxicity of these two complexes and to fully understand their mechanism of action.
2013
The dinuclear complexes [Pd 2 (L) 2 (bipy) 2 ] (1), [Pd 2 (L) 2 (phen) 2 ] (2), [Pt 2 (L) 2 (bipy) 2 ] (3) and [Pt 2 (L) 2 (phen) 2 ] (4), where bipy = 2,2 0 -bipyridine, phen = 1,10-phenanthroline and L = 2,2 0 -azanediyldibenzoic dianion) dibridged by H 2 L ligands have been synthesized and characterized. The binding of the complexes with fish sperm DNA (FS-DNA) were investigated by fluorescence spectroscopy. The results indicate that the four complexes bound to DNA with different binding affinity, in the order complex 4 > complex 3 > complex 2 > complex 1, and the complex 3 binds to DNA in both coordination and intercalative mode. Gel electrophoresis assay demonstrates the ability of the complexes to cleave the pBR 322 plasmid DNA. The cytotoxic activity of the complexes was tested against four different cancer cell lines. The four complexes exhibited cytotoxic specificity and significant cancer cell inhibitory rate. Crown j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l oc a t e / j i n o r g b i o calcd. (%) for C 96 H 68 N 12 O 16 Pd 4 Á H 2 O (1): C, 64.38; H, 3.38; N, 6.93. Found (%): C, 64.45; H, 3.30; N, 6.85; IR (cm À1 , s, strong; m, medium; w, weak): m(O-H) 3421(m); m(@C-H) 3083(m); m(C@O) 1636(s); m(C@C) 1500(s), 1452(m); m(C-N) 1327(s); m(C@O) 1281(m); m(C-H) 750(m). 1 H NMR (DMF-d 7 , 300 MHz); tt, two triplet; t, triplet; d, doublet: d 7.48(tt, J = 7.5 Hz, 2H, Hf, Hf 0 ), 7.86(2t, 4H, Hb, Hb 0 , Hg, Hg 0 ), 7.96(d, J = 6.5 Hz, 2H, He, He 0 ), 8.40(tt, J = 13.8 Hz, 2H, Hc, Hc 0 ), 8.46(d, J = 6.9 Hz, 2H, Hh, Hh 0 ), 8.70(d, J = 7.5 Hz, 2H, Ha, Ha 0 ), 8.72(d, 2H, Hd, Hd 0 ).
Journal of Chemical Sciences, 2012
The chelating ligands 3-chloro-6-(3-pyridyl-1-pyrazolyl)pyridazine (pp-Cl) and 3,6-bis(3-pyridyl-1-pyrazolyl)pyridazine (bppp), were prepared by the condensation of pyridylpyrazole and 3,6-dichloropyridazine. The mononuclear complexes [(η 6-arene)Ru(pp-Cl)Cl] + {η 6-arene = C 6 H 6 (1); p-i PrC 6 H 4 Me (2)}, [(η 5-C 5 Me 5)M(pp-Cl)] + {M = Rh (3); Ir (4)}, [(η 6-arene)Ru(bppp)Cl] + {η 6-arene = C 6 H 6 (5); pi PrC 6 H 4 Me (6)}, [(η 5-C 5 Me 5)M(bppp)] + {M =Rh (7); Ir (8)} as well as the binuclear complexes [{(η 6arene)RuCl} 2 (bppp)] 2+ {η 6-arene =C 6 H 6 (9); p-i PrC 6 H 4 Me (10)} and [{(η 5-C 5 Me 5)MCl} 2 (bppp)] 2+ {M = Rh (11); Ir (12)} have been synthesized from 3-chloro-6-(3-pyridyl-1-pyrazolyl)pyridazine (pp-Cl) or 3,6-bis(3-pyridyl-1-pyrazolyl)pyridazine (bppp) and the corresponding dimers [(η 6-arene)Ru(μ-Cl)Cl] 2 and [Cp*M(μ-Cl)Cl] 2 , respectively. All complexes were isolated as their hexafluorophosphate salts and characterized by IR, NMR, mass spectrometry and UV-visible spectroscopy. The molecular structures of [2]PF 6 and [7]PF 6 have been established by single crystal X-ray structure analysis.
Inorganica Chimica Acta, 2003
Os compostos hidrotris(2-mercaptotiazolil)borato de potássio, KMt, (1), e hidrotris(2metimazolil)borato de potássio, KTm, (2), foram preparados ao se reagir a amina tiol correspondente com KBH 4 . Foram caracterizados por métodos espectroscópicos e análise elementar. As estruturas no estado sólido de KMt.4H 2 O e do composto 2 foram determinadas por análises de difração de raios-X. A maior maciez do ânion em KMt.4H 2 O, em comparação com 2, é indicada pela ausência de interação entre ele e o cátion, que possui moléculas de água em sua esfera de coordenação. Em KMt.4H 2 O a geometria em torno do íon potássio é octaédrica distorcida e em 2, pirâmide de base quadrada distorcida. Em 2 o íon potássio está coordenado a dois átomos de enxofre dos anéis de um mesmo ânion e a três outros átomos de enxofre pertencentes a unidades KTm vizinhas. Ambos os compostos possuem uma estrutura polimérica.
European Journal of Medicinal Chemistry, 2008
New platinum(II) and platinum(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione and various halogen ions with general formula [PtL2X2] and [PtL2Cl4], where L is the organic ligand and X is Cl−, Br−, J−, were synthesized. The molecular formulae of all the complexes were confirmed by elemental analysis, IR, 1H, 13C NMR spectral analyses and molar conductivity. The cytotoxic effects of these complexes were examined
Chemistry: A European Journal, 2014
A wide variety of 2,5-di(2-pyridyl)pyrroles (dppHs) substituted at the C3 and C4 positions of the pyrrole core were obtained by direct condensation of a 2-pyridylcarboxaldehyde (2 equiv), an a-methylene ketone with at least one electron-withdrawing substituent and ammonium acetate. A novel 2,5-di(1,10-phenanthrolin-2-yl)pyrrole was also characterised. The dppHs provide a direct, quick entry to dipyridylpyrrolato (dpp À)-metal complexes. The meridial tridentate dpp À ligand is a useful anionic analogue of the terpyridyl ligand. The first (dpp)Ru complexes are described; the 3,4substitution of the central pyrrole significantly perturbs the potentials of the redox processes of these complexes. A [(dpp)Ru(bpy)(MeCN)] + (bpy = 2,2'-bipyridine) complex is an electrocatalyst for the reductive disproportionation of carbon dioxide to carbon monoxide and the carbonate ion.
Dalton Transactions, 2008
A series of new mononuclear and dinuclear platinum(II) compounds based on two bipyridyl systems, linked by an alkyl chain {1,2-bis[4-(4¢-methyl-2,2¢-bipyridinyl)]ethane, L2, (a), and 1,6-bis[4-(4¢-methyl-2,2¢-bipyridinyl)]hexane, L6, (b)} have been synthesized and characterized by IR and multinuclear and multidimensional NMR spectroscopy. The coordination sphere of the complexes, designed to give intercalating and/or covalent interactions with DNA, is completed only by exchangeable (Cl -, Ior H 2 O) and/or not leaving (chelate ethylenediamine, en) saturating ligands. Quenching of the DNA-ethidium fluorescence was performed in order to verify the intercalating capability of the water soluble compounds. Furthermore, the in vitro cytotoxicity of all water soluble complexes has been assessed with respect to cisplatin on platinum-sensitive human endometrium (HeLa) and platinum-resistant human breast (MCF-7) cancer cell lines.