@article{MTMT:34749525, title = {Synthesis of spiro[piperidine-4,3′-pyrrolo[3,4-c]quinolines via 1,3-dipolar cycloaddition of azomethine ylides and 3-Nitro-2(1H)-quinolones}, url = {https://m2.mtmt.hu/api/publication/34749525}, author = {Molnár, Márk and Gáti, Tamás and Bényei, Attila Csaba and Nyerges, Miklós}, doi = {10.1016/j.tetlet.2024.155001}, journal-iso = {TETRAHEDRON LETT}, journal = {TETRAHEDRON LETTERS}, volume = {139}, unique-id = {34749525}, issn = {0040-4039}, keywords = {X-ray diffraction; PIPERIDINE; 1,3-Dipolar cycloaddition; Quinolines; Azomethine ylide}, year = {2024}, eissn = {1873-3581} } @article{MTMT:34742565, title = {“Inverted” Cyclic(Alkyl)(Amino)Carbene (CAAC) Ruthenium Complex Catalyzed Isomerization Metathesis (ISOMET) of Long Chain Olefins to Propylene at Low Ethylene Pressure}, url = {https://m2.mtmt.hu/api/publication/34742565}, author = {Farkas, Vajk and Csókás, Dániel and Erdélyi, Ádám and Turczel, Gábor and Bényei, Attila Csaba and Nagy, Tibor and Kéki, Sándor and Pápai, Imre and Tuba, Róbert}, doi = {10.1002/advs.202400118}, journal-iso = {ADV SCI}, journal = {ADVANCED SCIENCE}, volume = {11}, unique-id = {34742565}, abstract = {Isomerization Metathesis (ISOMET) reaction is an emerging tool for “open loop” chemical recycling of polyethylene to propylene. Novel, latent N ‐Alkyl substituted Cyclic(Alkyl)(Amino)Carbene (CAAC)–ruthenium catalysts ( 5a‐Ru , 3b‐Ru – 6c‐Ru ) are developed rendering “inverted” chemical structure while showing enhanced ISOMET activity in combination with (RuHCl)(CO)(PPh 3 ) 3 ( RuH ) double bond isomerization co‐catalyst. Systematic investigations reveal that the steric hindrance of the substituents on nitrogen and carbon atom adjacent to carbene moiety in the CAAC ligand have significantly improved the catalytic activity and robustness. In contrast to the NHC‐Ru and CAAC‐Ru catalyst systems known so far, these systems show higher isomerization metathesis (ISOMET) activity (TON: 7400) on the model compound 1‐octadecene at as low as 3.0 bar optimized pressure, using technical grade (3.0) ethylene. The propylene content formed in the gas phase can reach up to 20% by volume.}, year = {2024}, eissn = {2198-3844}, orcid-numbers = {Farkas, Vajk/0000-0002-1189-0032; Csókás, Dániel/0000-0002-4150-477X; Erdélyi, Ádám/0009-0008-0715-8907; Turczel, Gábor/0000-0002-6753-6796; Nagy, Tibor/0000-0001-8568-914X; Pápai, Imre/0000-0002-4978-0365; Tuba, Róbert/0000-0001-8929-2713} } @article{MTMT:34558201, title = {Diastereoselective cycloaddition of isatin derived azomethine ylides to 3-nitro-2(1H)-quinolones}, url = {https://m2.mtmt.hu/api/publication/34558201}, author = {Molnár, Márk and Balázs, Barbara and Bényei, Attila Csaba and Nyerges, Miklós}, doi = {10.1016/j.tet.2024.133848}, journal-iso = {TETRAHEDRON}, journal = {TETRAHEDRON}, volume = {153}, unique-id = {34558201}, issn = {0040-4020}, year = {2024}, eissn = {1464-5416} } @article{MTMT:34555466, title = {Ruthenium complexes of new chiral phosphine‐amine‐ether ligands (Ru‐PNO) for asymmetric hydrogenation – the role of backbone chirality in pincer ligand design}, url = {https://m2.mtmt.hu/api/publication/34555466}, author = {Császár, Zsófia and Pőrgye, Zsanett E. and Farsang, Evelin and Kovács, Margit and Bényei, Attila Csaba and Bakos, József and Farkas, Gergely}, doi = {10.1002/aoc.7379}, journal-iso = {APPL ORGANOMET CHEM}, journal = {APPLIED ORGANOMETALLIC CHEMISTRY}, unique-id = {34555466}, issn = {0268-2605}, abstract = {New chiral phosphine‐amine‐ether (PNO) ligands of the general formula Ph 2 PCH(R 1 )(CH 2 ) n CH(R 1 )N(R 2 )CH(R 3 )CH 2 OMe, where R 1 , R 2 , and R 3 = H or Me, n = 0 or 1, and their ruthenium complexes of the type [RuCl 2 (PPh 3 )(PNO)] have been synthesized. The coordination compounds were characterized by 1D and 2D NMR spectroscopy, modeled by DFT calculations, and in one case analyzed by X‐ray crystallography. The combined spectroscopic and theoretical investigations revealed that the relative configuration of the stereogenic elements in the P–N and N–O backbone represents a crucial factor in determining the conformation of the pincer‐type chelates and may also affect the configuration of the coordinated stereogenic nitrogen in the NH subunit, an essential element of stereochemical communication in outer sphere bifunctional catalysis. The new complexes were applied in the asymmetric hydrogenation of fused ring bicyclic ketones (i.e., 1‐tetralone and 4‐chromanone derivatives), a challenging substrate class, where enantioselectivities up to 97% could be obtained. Based on the spectroscopic and theoretical studies and catalytic experiments, structural features affecting the stereochemistry of the coordination could be identified and a qualitative enantioinduction model has been proposed.}, keywords = {asymmetric hydrogenation; Chromanone}, year = {2024}, eissn = {1099-0739}, orcid-numbers = {Császár, Zsófia/0000-0002-7211-4790; Pőrgye, Zsanett E./0009-0007-1600-9316; Farsang, Evelin/0000-0003-2484-0920} } @article{MTMT:34492221, title = {Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation}, url = {https://m2.mtmt.hu/api/publication/34492221}, author = {Chniti, Sami and Pongrácz, Péter and Kollár, László and Bényei, Attila Csaba and Dörnyei, Ágnes and Takács, Attila}, doi = {10.1021/acs.joc.3c02337}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {89}, unique-id = {34492221}, issn = {0022-3263}, abstract = {Palladium-catalyzed aminocarbonylation of 3-iodochromone was studied in the presence of primary and secondary amines using atmospheric pressure of carbon monoxide as a carbonyl source. This procedure successfully provided a library of chromone-3-carboxamides and 3-substituted chroman-2,4-diones in 40 to 92% isolated yields. The reaction proceeded via highly chemoselective aminocarbonylation (up to 100%) in the presence of secondary amines by using monodentate or bidentate phosphine ligands. The tendency of 3-iodochromone substrate to undergo ANRORC rearrangement with N-nucleophiles was crucial to shift the reaction toward an unprecedented chemoselective carbonylative transformation, where a late-stage carbonyl insertion is favored concomitantly to the last ring-closure step. The proposed azaMichael addition/ring-opening/intramolecular aryloxycarbonylation sequence showed compatibility, uniquely, to primary amines when XantPhos was used as a ligand. The solid-state structures of chromone-3-carboxamide (2a) and chroman-2,4-dione (3s) were undoubtedly established by single-crystal XRD analysis. A catalytic cycle was proposed to rationalize the formation of the two types of carbonylated compounds.}, year = {2024}, eissn = {1520-6904}, pages = {1175-1183}, orcid-numbers = {Pongrácz, Péter/0009-0006-5782-2883; Dörnyei, Ágnes/0000-0002-6552-8522; Takács, Attila/0000-0003-2773-8788} } @article{MTMT:33785458, title = {Application of alkane-diyl based chiral phosphine-aminophosphine (P-NP) and thioether-aminophosphine (S-NP) ligands in Rh-catalyzed asymmetric hydrogenation}, url = {https://m2.mtmt.hu/api/publication/33785458}, author = {Farkas, Gergely and Császár, Zsófia and Farsang, Evelin and Bényei, Attila Csaba and Bakos, József}, doi = {10.1016/j.jorganchem.2023.122723}, journal-iso = {J ORGANOMET CHEM}, journal = {JOURNAL OF ORGANOMETALLIC CHEMISTRY}, volume = {994}, unique-id = {33785458}, issn = {0022-328X}, year = {2023}, eissn = {1872-8561}, orcid-numbers = {Császár, Zsófia/0000-0002-7211-4790; Farsang, Evelin/0000-0003-2484-0920} } @article{MTMT:33734265, title = {Half-Sandwich Type Platinum-Group Metal Complexes of C-Glucosaminyl Azines: Synthesis and Antineoplastic and Antimicrobial Activities}, url = {https://m2.mtmt.hu/api/publication/33734265}, author = {Kacsir, István and Sipos, Adrienn and Major, Evelin and Bajusz, Nikolett and Bényei, Attila Csaba and Buglyó, Péter and Somsák, László and Kardos, Gábor and Bay, Péter and Bokor, Éva}, doi = {10.3390/molecules28073058}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {28}, unique-id = {33734265}, issn = {1420-3049}, abstract = {While platinum-based compounds such as cisplatin form the backbone of chemotherapy, the use of these compounds is limited by resistance and toxicity, driving the development of novel complexes with cytostatic properties. In this study, we synthesized a set of half-sandwich complexes of platinum-group metal ions (Ru(II), Os(II), Ir(III) and Rh(III)) with an N,N-bidentate ligand comprising a C-glucosaminyl group and a heterocycle, such as pyridine, pyridazine, pyrimidine, pyrazine or quinoline. The sugar-containing ligands themselves are unknown compounds and were obtained by nucleophilic additions of lithiated heterocycles to O-perbenzylated 2-nitro-glucal. Reduction of the adducts and, where necessary, subsequent protecting group manipulations furnished the above C-glucosaminyl heterocycles in their O-perbenzylated, O-perbenzoylated and O-unprotected forms. The derived complexes were tested on A2780 ovarian cancer cells. Pyridine, pyrazine and pyridazine-containing complexes proved to be cytostatic and cytotoxic on A2780 cells, while pyrimidine and quinoline derivatives were inactive. The best complexes contained pyridine as the heterocycle. The metal ion with polyhapto arene/arenyl moiety also impacted on the biological activity of the complexes. Ruthenium complexes with p-cymene and iridium complexes with Cp* had the best performance in ovarian cancer cells, followed by osmium complexes with p-cymene and rhodium complexes with Cp*. Finally, the chemical nature of the protective groups on the hydroxyl groups of the carbohydrate moiety were also key determinants of bioactivity; in particular, O-benzyl groups were superior to O-benzoyl groups. The IC50 values of the complexes were in the low micromolar range, and, importantly, the complexes were less active against primary, untransformed human dermal fibroblasts; however, the anticipated therapeutic window is narrow. The bioactive complexes exerted cytostasis on a set of carcinomas such as cell models of glioblastoma, as well as breast and pancreatic cancers. Furthermore, the same complexes exhibited bacteriostatic properties against multiresistant Gram-positive Staphylococcus aureus and Enterococcus clinical isolates in the low micromolar range.}, keywords = {RHODIUM; Osmium; Staphylococcus aureus; iridium; RUTHENIUM; Enterococcus; cytostasis; azines; Ovarian cancer; methicillin-resistant Staphylococcus aureus (MRSA); Half-sandwich complex; vancomycin-resistant Enterococcus (VRE); C-glucosaminyl heterocycles}, year = {2023}, eissn = {1420-3049}, orcid-numbers = {Buglyó, Péter/0000-0002-6714-7598; Somsák, László/0000-0002-9103-9845} } @article{MTMT:33727451, title = {Effect of Molecular Weight on the Dissolution Profiles of PEG Solid Dispersions Containing Ketoprofen}, url = {https://m2.mtmt.hu/api/publication/33727451}, author = {Le Khanh, Ha Pham and Haimhoffer, Ádám and Nemes, Dániel and Józsa, Liza and Vasvári, Gábor and Budai, István and Bényei, Attila Csaba and Ujhelyi, Zoltán and Siposné Fehér, Pálma and Bácskay, Ildikó}, doi = {10.3390/polym15071758}, journal-iso = {POLYMERS-BASEL}, journal = {POLYMERS}, volume = {15}, unique-id = {33727451}, abstract = {Solid dispersions are typically binary systems with a hydrophilic matrix polymer and a lipophilic active substance. During formulation, the drug undergoes a crystalline to amorphous phase transition, which leads to a supersaturated solution providing enhanced bioavailability. The interaction of the active substance and the polymer is unique and influences the level of supersaturation. We aimed to investigate the relationship between low molecular weight polyethylene glycol derivates PEG 1000, 1500, and 2000 and ketoprofen regarding the effect of molecular weight. The physicochemical properties of solid dispersions prepared with hot melt homogenization and their respective physical mixtures were investigated with Fourier transform infrared spectroscopy, powder X-ray diffraction and scanning electron microscopy techniques. A phase solubility study was carried out in hydrochloric acid media which showed no difference between the three polymers, but the dissolution curves differed considerably. PEG 1000 had higher percentage of released drug than PEG 1500 and 2000, which had similar results. These results indicate that when multiple low molecular weight PEGs are suitable as matrix polymers of solid dispersions, the molecular weight has only limited impact on physicochemical characteristics and interactions and further investigation is needed to select the most applicable candidate.}, year = {2023}, eissn = {2073-4360}, pages = {1-15}, orcid-numbers = {Le Khanh, Ha Pham/0000-0003-4172-2184; Nemes, Dániel/0000-0002-5477-0540; Budai, István/0000-0002-8966-3817} } @article{MTMT:33683947, title = {Multifaceted Domino Knoevenagel‐Cyclization Reactions; Four Movements for 2H‐Chromenes and Chromans}, url = {https://m2.mtmt.hu/api/publication/33683947}, author = {Király, Sándor Balázs and Tóth, László and Kovács, Tibor and Bényei, Attila Csaba and Lisztes, Erika and Tóth, Balázs István and Bíró, Tamás and Kiss, Attila and E Kövér, Katalin and Mándi, Attila and Kurtán, Tibor}, doi = {10.1002/adsc.202300083}, journal-iso = {ADV SYNTH CATAL}, journal = {ADVANCED SYNTHESIS & CATALYSIS}, volume = {365}, unique-id = {33683947}, issn = {1615-4150}, abstract = {Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain was carried out to produce four series of chiral condensed heterocycles representing four novel skeletons and exhibiting antiproliferative activity. The cyclization step occurred with four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a new route to hydroxyindoles by an inverse Cadogan-type cyclization, in which the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and their stereoselectivity were studied by DFT calculations, based on which we proposed a mechanism for the multi-step cyclization to hydroxyindoles and explained the observed diastereoselectivity.}, keywords = {HETEROCYCLES; configuration determination; diastereoselectivity; domino reactions; cycloaddition; MOLECULAR DIVERSITY}, year = {2023}, eissn = {1615-4169}, pages = {3301-3319}, orcid-numbers = {Kiss, Attila/0000-0003-3601-5143} } @article{MTMT:33657380, title = {Triaza-tricyclanos – synthesis of a new class of tricyclic nucleoside analogues by stereoselective cascade cyclocondensation}, url = {https://m2.mtmt.hu/api/publication/33657380}, author = {Bege, Miklós and Herczeg, Mihály and Bakai-Bereczki, Ilona and Debreczeni, Nóra and Bényei, Attila Csaba and Herczegh, Pál and Borbás, Anikó}, doi = {10.1039/D3OB00154G}, journal-iso = {ORG BIOMOL CHEM}, journal = {ORGANIC & BIOMOLECULAR CHEMISTRY}, volume = {21}, unique-id = {33657380}, issn = {1477-0520}, abstract = {Conformationally constrained tricyclic morpholino-nucleosides containing three new chirality centers were prepared with full stereoselectivity, through two consecutive hemiaminal-imidazolidine cascade reactions.}, year = {2023}, eissn = {1477-0539}, pages = {2213-2219}, orcid-numbers = {Herczeg, Mihály/0000-0002-7938-9789; Bakai-Bereczki, Ilona/0000-0003-4601-7257; Borbás, Anikó/0000-0001-8462-4547} }