Publications by authors named "Petra Bombicz"

16 Publications

  • Page 1 of 1

Exploring Cyclic Aminopolycarboxylate Ligands for Sb(III) Complexation: PCTA and Its Derivatives as a Promising Solution.

Inorg Chem 2021 Sep 31;60(18):14253-14262. Epub 2021 Aug 31.

Department of Physical Chemistry, Faculty of Science and Technology, University of Debrecen, H-4032 Debrecen, Hungary.

In recent years Auger electron emitters have been suggested as promising candidates for radiotherapy with no side effects in cancer treatment. In this work we report a detailed coordination chemistry study of [Sb(PCTA)] (PCTA: 3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triacetic acid), a macrocyclic aminopolycarboxylate-type complex of antimony(III), whose Sb isotope could be a suitable low-energy electron emitter for radiotherapy. The thermodynamic stability of the chelate obtained by pH-potentiometry and UV-vis spectrophotometry is high enough (log = 23.2(1)) to prevent the hydrolysis of the metal ion near physiological pH. The formation of [Sb(PCTA)] is confirmed by NMR and electrospray ionization mass spectrometry measurements in solution; furthermore, the structure of [Sb(PCTA)]·NaCl·3HO and [Sb(PCTA)]·HCl·3HO is described by X-ray and density functional theory calculations. Consequently, the [Sb(PCTA)] is the first thermodynamically stable antimony(III) complex bearing polyamino-polycarboxylate macrocyclic platform. Our results demonstrate the potential of rigid (pyclen derivative) ligands as chelators for future applications of Sb(III) in a targeted radiotherapy based on the Sb isotope.
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http://dx.doi.org/10.1021/acs.inorgchem.1c01765DOI Listing
September 2021

Crystal structures of zinc(II) complexes with β-hydroxypyridinecarboxylate ligands: examples of structure-directing effects used in inorganic crystal engineering.

Acta Crystallogr B Struct Sci Cryst Eng Mater 2021 Apr 27;77(Pt 2):193-204. Epub 2021 Feb 27.

Centre for Structural Sciences, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, H-1117, Hungary.

The coordination properties of four hydroxypyridinecarboxylates, designed for the treatment of iron-overloading conditions as bidentate O,O'-donor ligands, have been studied with Zn in the solid state. The coordination compounds [Zn(A1)(HO)] (1), [Zn(A2)(HO)] (2), [Zn(A3)(HO)]·2HO (3) and [Zn(B1)(HO)]·4HO (4), where the ligands are 1-methyl-4-oxidopyridinium-3-carboxylate (A1, CHNO), 1,6-dimethyl-4-oxidopyridinium-3-carboxylate (A2, CHNO), 1,5-dimethyl-4-oxido-pyridinium-3-carboxylate (A3, CHNO) and 1-methyl-3-oxidopyridinium-4-carboxylate (B1, CHNO), have been synthesized and analysed by single-crystal X-ray diffraction. The ligands were chosen to probe (i) the electronic effects of inverting the positions of the O-atom donor groups (i.e. A1 versus B1) and (ii) the electronic and steric effects of the addition of a second methyl group in different positions on the pyridine ring. Two axially coordinated water molecules resulting in a six-coordinated symmetrical octahedron complement the bis-ligand complex of A1. Ligands A2 and A3 form five-coordinated trigonal bipyramidal complexes with one additional water molecule in the coordination sphere, which is a rarely reported geometry for Zn complexes. Ligand B1 shows a dimeric structure, where the two Zn dications have slightly distorted octahedral geometry and the pyridinolate O atom of the neighbouring complex bridges them. The coordination spheres of the Zn dications and the supramolecular structures are discussed in detail. The packing arrangements of 1-3 are similar, having alternating hydrophilic and hydrophobic layers, however the similarity is broken in 4. The obtained coordination geometries are compared with their previously determined Cu analogues. The study of the individual complexes is complemented with a comprehensive analysis of Zn complexes with oxygen donor ligands with data from the Cambridge Structural Database.
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http://dx.doi.org/10.1107/S2052520621000299DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8040096PMC
April 2021

Diterpenoids from Euphorbia dulcis with Potassium Ion Channel Inhibitory Activity with Selective G Protein-Activated Inwardly Rectifying Ion Channel (GIRK) Blocking Effect.

J Nat Prod 2018 11 9;81(11):2483-2492. Epub 2018 Nov 9.

Institute of Environmental Sciences, Faculty of Water and Environmental Management , Szent István University , 5540 Szarvas , Hungary.

Nine new (1-9) and two known (10, 11) jatrophane diterpenoids were isolated from the methanol extract of Euphorbia dulcis. The structure elucidation of the compounds was performed by means of extensive spectroscopic analysis, including HRESIMS, 1D (H, JMOD), and 2D (HSQC, HMBC, H-H-COSY, NOESY) NMR experiments. The absolute configuration of compound 1 was determined by single-crystal X-ray diffraction. The electrophysiological effects of compounds 1-11 and the five diterpenoids (12-16) previously isolated from Euphorbia taurinensis were investigated on stable transfected HEK-GIRK1/4 (Kir3.1/3.4) and HEK-hERG (Kv11.1) cell lines using automated patch-clamp equipment. The majority of the diterpenoids showed significant blocking activity on GIRK channels (60.8-88.7% at 10 μM), while compounds 1, 2, 9-11, 13, and 14 exerted notable inhibitory effects even at 1 μM concentration. None of the jatrophane diterpenoids interfered with the function of hERG proteins; however, compound 14 remarkably hampered K flow through hERG channels. These selective activities suggest that jatrophane diterpenoids may represent a group of potential lead compounds for the development of novel therapeutic agents against atrial fibrillation.
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http://dx.doi.org/10.1021/acs.jnatprod.8b00500DOI Listing
November 2018

Expanding the Pillararene Chemistry: Synthesis and Application of a 10 + 1 Functionalized Pillar[5]arene.

Org Lett 2017 09 21;19(17):4528-4531. Epub 2017 Aug 21.

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics , 1521 Budapest, Hungary.

A novel functionality was introduced in the pillararene family by the Claisen rearrangement of monoallyl pillar[5]arene. This new key derivative can lead to the formation of a 10 + 1 functionalized derivative, a useful scaffold for further derivatization. Except for the previously known monodeprotection reaction, all steps proceed efficiently with high yields and easy separation. In addition, a solvent-responsive pseudo[1]rotaxane was synthesized based on this novel functionality.
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http://dx.doi.org/10.1021/acs.orglett.7b02092DOI Listing
September 2017

Crystal structure of levomepromazine maleate.

Acta Crystallogr E Crystallogr Commun 2016 May 5;72(Pt 5):612-5. Epub 2016 Apr 5.

Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1519 Budapest, POB 206, Hungary.

The asymmetric unit of the title salt, C19H25N2OS(+)·C4H3O4 (-) [systematic name: (S)-3-(2-meth-oxy-pheno-thia-zin-10-yl)-N,N,2-tri-methyl-propanaminium hydrogen maleate], comprises two (S)-levomepromazine cations and two hydrogen maleate anions. The conformations of the two cations are similar. The major difference relates to the orientation of the meth-oxy substituent at the pheno-thia-zine ring system. The crystal components form a three-dimensional supra-molecular network via N-H⋯O, C-H⋯O and C-H⋯π inter-actions. A comparison of the conformations of the levomepromazine cations with those of the neutral mol-ecule and similar protonated mol-ecules reveals significant conformational flexibility of the pheno-thia-zine ring system and the substituent at the pheno-thia-zine N atom.
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http://dx.doi.org/10.1107/S2056989016004916DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908531PMC
May 2016

Modular Copper-Catalyzed Synthesis of Chromeno[4,3-b]quinolines with the Utilization of Diaryliodonium Salts.

J Org Chem 2016 Feb 8;81(3):920-31. Epub 2016 Jan 8.

MTA-ELTE, Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University , Pázmány Péter stny. 1/a, H-1117 Budapest, Hungary.

A novel, highly modular synthetic method with high functional group tolerance was developed for the construction of chromenoquinoline derivatives from arylpropynyloxy-benzonitriles and diaryliodonium triflates via an oxidative arylation-cyclization path. The copper(I) chloride catalyzed reaction is presumed to involve the formation of highly active arylcopper(III) species.
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http://dx.doi.org/10.1021/acs.joc.5b02490DOI Listing
February 2016

Supramolecular interactions in the solid state.

IUCrJ 2015 Nov 22;2(Pt 6):675-90. Epub 2015 Sep 22.

Division of Advanced Materials Science, Pohang University of Science and Technonlogy , 77 Cheongam-Ro Nam-Gu, Pohang 790-784, South Korea.

In the last few decades, supramolecular chemistry has been at the forefront of chemical research, with the aim of understanding chemistry beyond the covalent bond. Since the long-range periodicity in crystals is a product of the directionally specific short-range intermolecular interactions that are responsible for molecular assembly, analysis of crystalline solids provides a primary means to investigate intermolecular interactions and recognition phenomena. This article discusses some areas of contemporary research involving supramolecular interactions in the solid state. The topics covered are: (1) an overview and historical review of halogen bonding; (2) exploring non-ambient conditions to investigate intermolecular interactions in crystals; (3) the role of intermolecular interactions in morphotropy, being the link between isostructurality and polymorphism; (4) strategic realisation of kinetic coordination polymers by exploiting multi-interactive linker molecules. The discussion touches upon many of the prerequisites for controlled preparation and characterization of crystalline materials.
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http://dx.doi.org/10.1107/S2052252515014608DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645112PMC
November 2015

Utilization of Copper-Catalyzed Carboarylation-Ring Closure for the Synthesis of New Oxazoline Derivatives.

Org Lett 2015 Sep 18;17(17):4136-9. Epub 2015 Aug 18.

MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University , Pázmány Péter stny. 1/a, H-1117 Budapest, Hungary.

A copper-catalyzed carboarylation-ring-closure strategy was used for the modular synthesis of oxazolines via the reaction of 1-aryl- and 1-alkylpropargylamides and diaryliodonium salts. The novel approach enables the efficient, modular synthesis of oxazoline derivatives bearing fully substituted exo double bonds.
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http://dx.doi.org/10.1021/acs.orglett.5b01860DOI Listing
September 2015

Transformation of Zwitterionic Pyridine Derivatives to a Spiro-Fused Ring System: Azoniabenzo[de]fluorine. Synthesis and Mechanistic Rationalization.

J Org Chem 2015 Jan 5;80(1):174-9. Epub 2014 Dec 5.

Research Centre for Natural Sciences, Institute of Organic Chemistry, Hungarian Academy of Sciences, Magyar tudósok körútja 2, H-1117 Budapest, Hungary.

Reaction of aryl- and benzylsulfanopyridinium amidates bearing a methyl group in position 6 with 2 equiv of diphenylketene afforded a spiro-fused ring system: azoniabenzo[de]fluorine. By use of an excess amount of ketene, a distinct reaction was observed via which a 1H-pyrrolo[3,2-b]pyridin-2(3H)-one derivative was furnished. The structure of the tetracyclic spiro-fused ring system was unambiguously confirmed by X-ray diffraction, and its formation was rationalized by DFT calculations.
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http://dx.doi.org/10.1021/jo5022663DOI Listing
January 2015

Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators.

Bioorg Med Chem 2012 Jul 5;20(14):4258-70. Epub 2012 Jun 5.

Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary.

N-dienylphenothiazines synthesized from tetrazolo[1,5-a]pyridinium salts by treatment with phenothiazine were subjected to catalytic hydrogenation to yield N-butylphenothiazines, whereas transformation of these dienes with borane dimethyl sulfide (BH(3) × Me(2)S) resulted in selective hydroboration of one double bond and full reduction of the other double bond to give 2-hydroxybutylphenothiazines. Position of the hydroxyl group was supported by NMR spectroscopy and verified by X-ray analysis. Comparison of MDR modulatory activity of the new derivatives revealed that the hydroxybutyl compounds are promising candidates for development of novel MDR inhibitors.
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http://dx.doi.org/10.1016/j.bmc.2012.05.065DOI Listing
July 2012

Influence of benzylamine on the resolution of ibuprofen with (+)-(R)-phenylethylamine via supercritical fluid extraction.

Chirality 2009 Jun;21(6):628-36

Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, Hungary.

The resolution of racemic ibuprofen was studied by partial diastereomer salt formation. The resolution was performed via two methods: resolution with (+)-(R)-phenylethylamine as chiral agent and resolution with a mixture of (+)-(R)-phenylethylamine and benzylamine. The diastereomers and unreacted enantiomers were separated by supercritical fluid extraction with carbon dioxide at 15 MPa and 33 degrees C. The influence of the achiral benzylamine on the resolution efficiency was studied by varying the concentrations of the structurally related amines in their mixtures, keeping the sum molar ratio of the amines to racemic ibuprofen constant at 0.55 +/- 0.02. The presence of benzylamine positively influenced the resolution efficiency at certain concentrations. The crystal structure of the salts of (+)-(R)-phenylethylamine with (-)-(R)-ibuprofen and (+)-(S)-ibuprofen, respectively, as well as the cocrystal of the benzylamine-ibuprofen salt with neutral ibuprofen molecules are presented. These structures were determined by single crystal X-ray diffraction, proving the significantly different stoichiometry of the related amines with the chiral acid, in accordance with mass balance calculations.
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http://dx.doi.org/10.1002/chir.20655DOI Listing
June 2009

Optical resolution of 1-(1-naphthyl)ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair.

Chirality 2009 Mar;21(3):331-8

Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, H-1521 Budapest, Hungary.

Optical resolution methods were established for racemic 1-(1-naphthyl) ethylamine. The resolving agents were synthesized by N-derivatizing (R)-1-(1-naphthyl) ethylamine with dicarboxylic acids. Oxalic, malonic, and succinic acid derivatives were found to be suitable resolving agents. These resolutions are parallel to a series of optical resolutions of 1-phenylethylamine which had been previously performed by our research group using similar derivative resolving agents (Balint et al., Tetrahedron: Asymmetry 2001;12:1511-1518.) The comparison of the results of the enantiomer separations is performed. The diastereomeric salts formed with (R)-N-[1-(1-naphthyl)ethyl]oxalamic acid were investigated by single crystal X-ray diffraction. The crystal structures were compared with the previously published structures of the diastereomers of the phenyl-substituted analogue, namely (R)- and (S)-1-phenylethylammonium (R)-N-(1-phenylethyl)oxalamates (Balint et al., Tetrahedron: Asymmetry 2001;12:1511-1518).
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http://dx.doi.org/10.1002/chir.20535DOI Listing
March 2009

Highly enantioselective organocatalytic conjugate addition of nitromethane to benzylidene acetones.

Chirality 2008 Nov;20(10):1120-6

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary.

Six active 4-aryl-5-nitro-pentan-2-ones were synthesized enantioselectively from the corresponding 5-aryl-butenones by asymmetric Michael addition of nitromethane using an imidazolidine-type enantioselective organocatalyst. The ee ratio of the products were between 67 and 100%, determined by HPLC with Chiracel OD. Molecular and crystal structure of 3,4-methylenedioxy-phenyl-5-nitro-pentan-2-one has been studied by single crystal X-ray diffraction.
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http://dx.doi.org/10.1002/chir.20567DOI Listing
November 2008

Modified Mg : Al hydrotalcite in the synthesis of oxazolidin-2-ones.

Org Biomol Chem 2005 Mar 10;3(6):967-9. Epub 2005 Feb 10.

Department of Organic Chemical Technology, Budapest University of Technology and Economics, H-1521, Budapest, Hungary.

The modified Mg : Al (3 : 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield.
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http://dx.doi.org/10.1039/b418848aDOI Listing
March 2005

Supramolecular [6]chochin and "Big Mac" made from chiral Piedfort assemblies.

Chemistry 2003 Aug;9(16):3741-7

Institute of Chemistry Chemical Research Center, Hungarian Academy of Science PO Box 17, 1525 Budapest, Hungary.

Facile chemical synthesis of the natural chiral-pool-derived host 1 and its subsequent crystallization ("supramolecular synthesis") from different solvents yielded crystalline assemblies. Crystal structure determinations of five of the so formed solvent-inclusion compounds (1 a-1 e) reveal hexagonal symmetries in four cases. The structural characteristics of these chiral host-guest ensembles with varying stoichiometries can be best described as assemblies formed through intra-pair hydrogen bridges of host molecules into Piedfort pairs of differing complexity. Hitherto undescribed, these Piedfort pairs also form even larger regular assemblies that we designate "Big Mac"-like shapes. In the only nonhexagonal case, six independent host molecules form a huge supramolecular analogue of [6]benzocyclophane, also known as [6]chochin, extending this giant supermolecule through intermolecular hydrogen bonds into macroscopic (mm-size) dimensions. As all these crystals are inherently chiral, and new model systems for solid-state applications can be envisaged.
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http://dx.doi.org/10.1002/chem.200304969DOI Listing
August 2003

A classical example of a disappearing polymorph and the shortest intermolecular H...H separation ever found in an organic crystal structure.

Angew Chem Int Ed Engl 2003 Apr;42(17):1957-60

Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, PBox 17, 1525 Budapest, Hungary.

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http://dx.doi.org/10.1002/anie.200219504DOI Listing
April 2003
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