Metallkomplexe mit biologisch wichtigen Liganden, CXL. Halbsandwich-Komplexe von Ruthenium(II), Rhodium(III), Iridium(III) sowie Palladium(II)-und Platin(II)-Komplexe mit N,O-Chelaten von Fluor-und Thiophen-haltigen α-Aminosäuren/Metal Complexes of Biologically Important Ligands, CXL. Halfsandwich Complexes of Ruthenium(II), Rhodium(III), Iridium(III) and Palladium(II), Platinum(II) Complexes with N, O-Chelates of Fluorine and Thiophene Containing α-Amino Acids

Koch, Daniela; Beck, Wolfgang

doi:10.1515/znb-2001-1204

Cited by 4 publications

(4 citation statements)

References 7 publications

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“…Anal. (C6H13N4F3O5Pt) C, H, N. MS MALDI-TOF: M + (% relative abundance) ) 410 (23), 411 (33), 412 (29), 413 (9), 414 (6). NMR data: 1 H, δ ) 2.60 (4H, pseudo triplet with platinum satellites, 3 JPt-H ) 45.2 Hz) and 1.85 (3H, s) ppm; 19 F, δ ) -75.89 ppm; 195 Pt, δ ) -2470 ppm (br) (D2O, pH* 6.00).…”

Section: Preparation Of the Platinum Complexes [Pt(no 3)2-(me2phen)]mentioning

confidence: 99%

“…To the best of our knowledge this is the first reported synthesis and characterization of platinum(II) complexes containing an optically pure R-Tfm-AA. 33…”

Section: Introductionmentioning

confidence: 99%

“…In this paper we report on a series of platinum(II) complexes containing optically pure α-trifluoromethylalanine as ligand (Scheme ). To the best of our knowledge this is the first reported synthesis and characterization of platinum(II) complexes containing an optically pure α-Tfm-AA 1 Sketches of the Novel Compounds a a The chirality of the aminoacid is not indicated. …”

Section: Introductionmentioning

confidence: 99%

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Platinum-Based Antitumor Drugs Containing Enantiomerically Pure α-Trifluoromethyl Alanine as Ligand

et al. 2005

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Synthetic amino acids such as fluorinated alpha-amino acids are currently actively investigated for their biological activity. Herein, we report on the synthesis and characterization of platinum complexes containing an N,O-chelated pure enantiomer of alpha-trifluoromethylalanine (alpha-Tfm-Ala). The compounds are either anionic, K[PtCl2(alpha-Tfm-Ala)], or cationic, [PtAm2(alpha-Tfm-Ala)](NO3) (Am2= (NH3)2, ethylendiamine (en), 1,10-phenanthroline (phen), and 2,9-dimethyl-1,10-phenanthroline (Me2phen)). All complexes are highly soluble in water and have been fully characterized by NMR spectroscopy. In vitro cytotoxicity assays on different human tumor cell lines have been performed on some of the isolated compounds. [Pt(NH3)2(alpha-Tfm-Ala)] with R configuration of the amino acid proved to have an activity comparable to that of the reference compound cisplatin. Flow cytometric analysis on NCI-H460 tumor cells (absence of G2/M arrest, which instead is observed in the case of cisplatin) suggests a mechanism of action different from that of cisplatin.

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Section: Preparation Of the Platinum Complexes [Pt(no 3)2-(me2phen)]mentioning

confidence: 99%

“…To the best of our knowledge this is the first reported synthesis and characterization of platinum(II) complexes containing an optically pure R-Tfm-AA. 33…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Platinum-Based Antitumor Drugs Containing Enantiomerically Pure α-Trifluoromethyl Alanine as Ligand

et al. 2005

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“…Stoichiometric model reactions give an insight into the transmetallation step. To prevent the functional groups of the phenylalanine moiety from coordinating to the transition metal, as described in the literature, both functionalities were protected by either acetyl or ester moieties –…”

Section: Introductionmentioning

confidence: 99%

Suzuki–Miyaura Cross‐Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step

Kohlmann

Braun

Laubenstein

et al. 2017

Chemistry A European J

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Metallkomplexe mit biologisch wichtigen Liganden. CLXV N,O‐Chelat‐Komplexe von α‐Aminosäureanionen mit cyclopalladiertem N,N‐Dimethylferrocencarbothiamid

Hauck

Sünkel

Beck

2006

Zeitschrift anorg allge chemie

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A short literature review on the reactions of various chlorobridged complexes with α-aminoacidates, α-amino acid esters, peptide ester or derivatives of amino acids is given. The chloro bridged o-palladated N,N-dimethylferrocenecarbothioamide [(fct)Pd(µ-Cl) 2 Pd(fct)] reacts with the anions of glycine, L-alanine, L-proline, L-valine, L-phenylalanine, L-leucine, L-isoleucine to give the N,O-chelates [(fct)Pd(N,O-α-aminocarboxylate)] Einleitung Chloroverbrückte Komplexe [2] L n M(µ-Cl) 2 ML n sind ideale Ausgangsverbindungen für die Synthese von metallorganischen Komplexen mit Aminosäuren und deren Derivaten [3]. Sie setzen sich mit den Anionen von Aminosäuren unter Spaltung der Chlorobrücken und Substitution von Chlorid zu N,O-Chelaten L n M(NH 2 CHRCO 2 ) um. Mit Neutralliganden wie a-Aminosäure-bzw. Peptid-Estern oder Schiff-Basen von Aminosäuren reagieren chloroverbrückte Komplexe meist nur unter Öffnung der Chlorobrücken. Im Folgenden sind die halogenoverbrückten Komplexe aufgeführt, die mit Aminosäure-Anionen und Aminosäure-Derivaten umgesetzt wurden: [(ON) 2 M(µ-Cl)] 2 (M ϭ Fe,Co) [4], [(allyl)Pd(µ-Cl)] 2305 (1Ϫ7). Due to the planary chirality of the unsymmetrically disubstituted cyclopentadienyl iron moiety of fct the complexes 2Ϫ7 with optically active amino acidate ligands are formed as a mixture of two diastereoisomers, which can be detected by their NMR spectra.

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Cited by 4 publications

References 7 publications

Platinum-Based Antitumor Drugs Containing Enantiomerically Pure α-Trifluoromethyl Alanine as Ligand

Platinum-Based Antitumor Drugs Containing Enantiomerically Pure α-Trifluoromethyl Alanine as Ligand

Suzuki–Miyaura Cross‐Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step

Metallkomplexe mit biologisch wichtigen Liganden. CLXV N,O‐Chelat‐Komplexe von α‐Aminosäureanionen mit cyclopalladiertem N,N‐Dimethylferrocencarbothiamid

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