Synthesis of new chiral diimine palladium(II) and nickel(II) complexes bearing oxazoline- and myrtanyl-based nitrogen ligands. Crystal structure of the C2-symmetric complex [{(1R,2S)-inda-box}PdCl2]

Abu‐Surrah, Adnan S.; Kettunen, Mika; Lappalainen, Kristian; Piironen, Ulla; Klinga, Martti; Leskelä, Markku

doi:10.1016/s0277-5387(01)00952-4

Cited by 30 publications

(7 citation statements)

References 22 publications

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“…Aiming at overcoming cis → trans isomerisation around the metal ion, the presence of bidentate amines has been an almost constant feature of new Pd(II) agents [90,94,240,[281][282][283][284]. Various chelating nonleaving groups have been evaluated, from amine neutral ligands such as ethylenediamine [262,285,286] and diaminocyclohexane (DACH) [240] to alkylaminophosphine oxides [274], mercaptoimidazoles, and pyridine and pyrimidine derivatives [275,276,287].…”

Section: Palladium For Platinum Substitution In Polyamine Complexesmentioning

confidence: 99%

“…Various chelating nonleaving groups have been evaluated, from amine neutral ligands such as ethylenediamine [262,285,286] and diaminocyclohexane (DACH) [240] to alkylaminophosphine oxides [274], mercaptoimidazoles, and pyridine and pyrimidine derivatives [275,276,287]. Several strategies have therefore been attempted to imposing a lower liability to palladium(II) complexes, from the use of polydentate amines, for example, ethylenediamine [93,95], NH 3 and diaminocyclohexane [288], or tetradentate phenanthroline-type N 4 ligands [289] to the combination of two distinct molecular sub units around a metal centre, for example, a diamine and a pyridine derivative [282] or tridentate NNS ligands [267]. As to the leaving groups, two chlorides, a nitrato or a chelating dicarboxylate moiety have yielded good results.…”

Section: Palladium For Platinum Substitution In Polyamine Complexesmentioning

confidence: 99%

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Platinum and Palladium Polyamine Complexes as Anticancer Agents: The Structural Factor

Marques

2013

ISRN Spectroscopy

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Since the introduction of cisplatin to oncology in 1978, Pt(II) and Pd(II) compounds have been intensively studied with a view to develop the improved anticancer agents. Polynuclear polyamine complexes, in particular, have attracted special attention, since they were found to yield DNA adducts not available to conventional drugs (through long-distance intra- and interstrand cross-links) and to often circumvent acquired cisplatin resistance. Moreover, the cytotoxic potency of these polyamine-bridged chelates is strictly regulated by their structural characteristics, which renders this series of compounds worth investigating and their synthesis being carefully tailored in order to develop third-generation drugs coupling an increased spectrum of activity to a lower toxicity. The present paper addresses the latest developments in the design of novel antitumor agents based on platinum and palladium, particularly polynuclear chelates with variable length aliphatic polyamines as bridging ligands, highlighting the close relationship between their structural preferences and cytotoxic ability. In particular, studies by vibrational spectroscopy techniques are emphasised, allowing to elucidate the structure-activity relationships (SARs) ruling anticancer activity.

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Section: Palladium For Platinum Substitution In Polyamine Complexesmentioning

confidence: 99%

Section: Palladium For Platinum Substitution In Polyamine Complexesmentioning

confidence: 99%

Platinum and Palladium Polyamine Complexes as Anticancer Agents: The Structural Factor

Marques

2013

ISRN Spectroscopy

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“…As an augmentation to our studies upon both the coordination chemistry of heteroatom-containing ligands [27,28] and their catalytic application [15][16][17][18][29][30][31], we now report on the application of some iron(II) and cobalt(II) complexes containing aldimine 2,6-bis[(imino)methyl]pyridine with bulky myrtanyl-, bornyl or naphthyl groups on the axial position for the polymerization of tert-butyl acrylate (t-BA) in the presence of MAO as a cocatalyst. In contrast to the poor activity observed for the aldimine-based pentacoordinated iron(II) catalyst systems bearing aromatic or aliphatic terminal moieties toward polymerization of nonpolar alkenes, those systems showed higher monomer conversion in polymerization of tert-butylacrylate.…”

Section: Introductionmentioning

confidence: 96%

Aldimine 2,6-bis(imino)pyridine iron(II) and cobalt(II)/methyl aluminoxane catalyst systems for polymerization of tert-butylacrylate

Abu‐Surrah

Lappalainen

Leskelä

et al. 2009

Transition Met Chem

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Aldimine 2,6-bis[(imino)methyl]pyridine iron(II) (1, 4, and 6) and cobalt(II) (3 and 5) complexes bearing bulky cycloaliphatic (bornyl and myrtanyl) or aromatic (naphthyl) terminal groups have been applied successfully, after activation with methyl aluminoxane (MAO), as catalysts for the polymerization of tert-butylacrylate. For comparison reasons, complex 2 that contains the ketimine ligand, 2,6-bis[(-)-cismyrtanylimino)ethyl]pyridine (BMEP), has also been utilized. All studied complexes showed moderate polymerization activities, and they produced high molar mass syndiorichatactic polymers. Surprisingly, the aldimine-based catalyst systems showed comparable activities compared with the corresponding ketimine complex (2), and they produced high molar mass polymers. In addition, complexes with bulky terminal cycloaliphatic substituents on the tridentate aldimine ligands showed higher polymerization activity compared with the aromatic ones (6). Polymerization activity and polymer molar masses are dependent on the ligand framework.

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“…To date, although the X-ray structures of several metal complexes of chiral bisoxazolines have been reported [6][7][8][9][10], there appear to have been no structural studies of chiral bisoxazolines alone. Here, we report a study of the bisoxazoline, 1, using ab initio density functional theory (DFT) [11,12], in combination with vibrational unpolarised absorption (IR) and vibrational circular dichroism (VCD) [13][14][15][16] spectroscopies.…”

Section: Introductionmentioning

confidence: 99%

Conformational Analysis in Solution of a Chiral BisoxazolineMolecule: Vibrational Circular Dichroism Spectroscopy and DensityFunctional Theory Study

Aamouche

Stephens

2011

International Journal of Spectroscopy

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The conformations of the chiral bisoxazoline: 2,2 -methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (also named IndaBOX), have been studied. Density functional theory (DFT) calculations identify four inequivalent stable conformations. Two, I and II have, C 2 symmetry; two, III and IV, have C 1 symmetry. The electronic energies of I-IV are ordered: I < II < III < IV. The span in energy is <1.0 kcal/mole. Vibrational unpolarised absorption and circular dichroism spectra have been predicted for the four conformations using DFT. Comparison of population-weighted spectra to experimental spectra of CHCl 3 and CDCl 3 solutions in mid-IR region strongly supports the DFT predictions of the number, structures, and relative energies of the conformations of IndaBOX. This shows that DFT predicts spectra with a high degree of reliability. We will undoubtedly illustrate the advantage added by vibrational circular dichroism spectroscopy in conformational analysis and in the absolute configuration determination.

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Synthesis of new chiral diimine palladium(II) and nickel(II) complexes bearing oxazoline- and myrtanyl-based nitrogen ligands. Crystal structure of the C2-symmetric complex [{(1R,2S)-inda-box}PdCl2]

Cited by 30 publications

References 22 publications

Platinum and Palladium Polyamine Complexes as Anticancer Agents: The Structural Factor

Platinum and Palladium Polyamine Complexes as Anticancer Agents: The Structural Factor

Aldimine 2,6-bis(imino)pyridine iron(II) and cobalt(II)/methyl aluminoxane catalyst systems for polymerization of tert-butylacrylate

Conformational Analysis in Solution of a Chiral BisoxazolineMolecule: Vibrational Circular Dichroism Spectroscopy and DensityFunctional Theory Study

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