@article{MTMT:34801853, title = {Continuous-flow hydrogenation of cinnamaldehyde over catalysts derived from modified CoAl4 layered double hydroxides incorporating Mn, Ni, Cu and Zn ions}, url = {https://m2.mtmt.hu/api/publication/34801853}, author = {Mészáros, Rebeka Ildikó and Szabó, Vivien and Kutus, Bence and Baán, Kornélia and Kónya, Zoltán and Kukovecz, Ákos and Sipos, Pál Miklós and Szabados, Márton}, doi = {10.1016/j.apcata.2024.119738}, journal-iso = {APPL CATAL A-GEN}, journal = {APPLIED CATALYSIS A-GENERAL}, volume = {679}, unique-id = {34801853}, issn = {0926-860X}, year = {2024}, eissn = {1873-3875}, orcid-numbers = {Mészáros, Rebeka Ildikó/0000-0002-2860-3431; Kutus, Bence/0000-0001-5023-0152; Baán, Kornélia/0000-0001-7511-4422; Kónya, Zoltán/0000-0002-9406-8596; Kukovecz, Ákos/0000-0003-0716-9557; Sipos, Pál Miklós/0000-0003-1407-0950; Szabados, Márton/0000-0002-7588-335X} } @article{MTMT:34791082, title = {Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers}, url = {https://m2.mtmt.hu/api/publication/34791082}, author = {Háznagy, Márton Benedek and Csámpai, Antal and Ugrai, Imre and Barnabás, Molnár and Matti, Haukka and Szakonyi, Zsolt}, doi = {10.3390/ijms25084325}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {25}, unique-id = {34791082}, issn = {1661-6596}, abstract = {A library of regioisomeric monoterpene-based aminodiols was synthesised and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The synthesis of the first type of aminodiols was achieved starting from (−)-8,9-dihydroperillaldehyde via reductive amination, followed by Boc protection and dihydroxylation with the OsO4/NMO system. Separation of formed stereoisomers resulted in a library of aminodiol diastereoisomers. The library of regioisomeric analogues was obtained starting from (−)-8,9-dihydroperillic alcohol, which was transformed into a mixture of allylic trichloroacetamides via Overman rearrangement. Changing the protecting group to a Boc function, the protected enamines were subjected to dihydroxylation with the OsO4/NMO system, leading to a 71:16:13 mixture of diastereoisomers, which were separated, affording the three isomers in isolated form. The obtained primary aminodiols were transformed into secondary derivatives. The regioselectivity of the ring closure of the N-benzyl-substituted aminodiols with formaldehyde was also investigated, resulting in 1,3-oxazines in an exclusive manner. To explain the stability difference between diastereoisomeric 1,3-oxazines, a series of comparative theoretical modelling studies was carried out. The obtained potential catalysts were applied in the reaction of aromatic aldehydes and diethylzinc with moderate to good enantioselectivities (up to 94% ee), whereas the opposite chiral selectivity was observed between secondary aminodiols and their ring-closed 1,3-oxazine analogues.}, year = {2024}, eissn = {1422-0067}, orcid-numbers = {Csámpai, Antal/0000-0003-2107-7309; Matti, Haukka/0000-0002-6744-7208; Szakonyi, Zsolt/0000-0003-2432-8409} } @article{MTMT:34743321, title = {The Impact of C-3 Side Chain Modifications on Kynurenic Acid: A Behavioral Analysis of Its Analogs in the Motor Domain}, url = {https://m2.mtmt.hu/api/publication/34743321}, author = {Martos, Diána and Lőrinczi, Bálint and Szatmári, István and Vécsei, László and Tanaka, Masaru}, doi = {10.3390/ijms25063394}, journal-iso = {INT J MOL SCI}, journal = {INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}, volume = {25}, unique-id = {34743321}, issn = {1661-6596}, abstract = {The central nervous system (CNS) is the final frontier in drug delivery because of the blood–brain barrier (BBB), which poses significant barriers to the access of most drugs to their targets. Kynurenic acid (KYNA), a tryptophan (Trp) metabolite, plays an important role in behavioral functions, and abnormal KYNA levels have been observed in neuropsychiatric conditions. The current challenge lies in delivering KYNA to the CNS owing to its polar side chain. Recently, C-3 side chain-modified KYNA analogs have been shown to cross the BBB; however, it is unclear whether they retain the biological functions of the parent molecule. This study examined the impact of KYNA analogs, specifically, SZR-72, SZR-104, and the newly developed SZRG-21, on behavior. The analogs were administered intracerebroventricularly (i.c.v.), and their effects on the motor domain were compared with those of KYNA. Specifically, open-field (OF) and rotarod (RR) tests were employed to assess motor activity and skills. SZR-104 increased horizontal exploratory activity in the OF test at a dose of 0.04 μmol/4 μL, while SZR-72 decreased vertical activity at doses of 0.04 and 0.1 μmol/4 μL. In the RR test, however, neither KYNA nor its analogs showed any significant differences in motor skills at either dose. Side chain modification affects affective motor performance and exploratory behavior, as the results show for the first time. In this study, we showed that KYNA analogs alter emotional components such as motor-associated curiosity and emotions. Consequently, drug design necessitates the development of precise strategies to traverse the BBB while paying close attention to modifications in their effects on behavior.}, year = {2024}, eissn = {1422-0067}, orcid-numbers = {Lőrinczi, Bálint/0000-0001-7773-0034; Szatmári, István/0000-0002-8571-5229; Vécsei, László/0000-0001-8037-3672} } @article{MTMT:34721105, title = {Synthesis of bioactive evodiamine and rutaecarpine analogues under a ball milling condition}, url = {https://m2.mtmt.hu/api/publication/34721105}, author = {Hu, Hao-Chun and Yu, Szu-Yin and Tsi, Yi-Hong and Hsieh, Pei-Wen and Wang, Hui-Chun and Chen, Yan-Ning and Chuang, Ya-Ting and Lee, Min-Yu and Chang, Hsueh-Wei and Hu, Hao-Chun and Wu, Yang-Chang and Chang, Fang-Rong and Szatmári, István and Fülöp, Ferenc}, doi = {10.1039/D4OB00056K}, journal-iso = {ORG BIOMOL CHEM}, journal = {ORGANIC & BIOMOLECULAR CHEMISTRY}, volume = {22}, unique-id = {34721105}, issn = {1477-0520}, abstract = {Mechanochemical reactions achieved by processes such as milling and grinding offer a promising alternative to traditional solution-based chemistry. This approach not only eliminates the need for large quantities of solvents,...}, year = {2024}, eissn = {1477-0539}, pages = {2620-2629}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:34715381, title = {Cyclic Amines Coupled to Indole Derivatives With Improved Efflux Pump Inhibiting Activity in Bacteria and Cancer Cells}, url = {https://m2.mtmt.hu/api/publication/34715381}, author = {Hegedűs, Dóra and Szemerédi, Nikoletta and Gábor, Maja and Sas, Judit and Belasri, Khadija and Szatmári, István and Spengler, Gabriella}, doi = {10.21873/anticanres.16910}, journal-iso = {ANTICANCER RES}, journal = {ANTICANCER RESEARCH}, volume = {44}, unique-id = {34715381}, issn = {0250-7005}, year = {2024}, eissn = {1791-7530}, pages = {1149-1160}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Spengler, Gabriella/0000-0001-8085-0950} } @article{MTMT:34689790, title = {Tryptophanhydroxamic Acid-Stabilized Ultrasmall Gold Nanoclusters: Tuning the Selectivity for Metal Ion Sensing}, url = {https://m2.mtmt.hu/api/publication/34689790}, author = {Gombár, Gyöngyi and Ungor, Ditta Anita and Szatmári, István and Juhász, Ádám and Csapó, Edit}, doi = {10.3390/nano14050434}, journal-iso = {NANOMATERIALS-BASEL}, journal = {NANOMATERIALS}, volume = {14}, unique-id = {34689790}, abstract = {Sub-nanometer-sized gold nanoclusters (Au NCs) were prepared via the spontaneous reduction of [AuCl4]−- ions with a hydroxamate derivative of L-tryptophan (Trp) natural amino acid (TrpHA). The prepared TrpHA-Au NCs possess intense blue emission (λem = 470 nm; λex = 380 nm) with a 2.13% absolute quantum yield and 1.47 ns average lifetime. The Trp-stabilized noble metal NCs are excellent metal ion sensors for Fe3+, but in this work, we highlighted that the incorporation of the hydroxamate functional group with an excellent metal ion binding capability can tune the selectivity and sensitivity of these NCs, which is a promising way to design novel strategies for the detection of other metal ions as well. Moreover, their simultaneous identification can also be realized. By decreasing the sensitivity of our nano-sensor for Fe3+ (limit of detection (LOD) ~11 µM), it was clearly demonstrated that the selectivity for Cu2+-ions can be significantly increased (LOD = 3.16 µM) in an acidic (pH = 3–4) condition. The surface-bounded TrpHA molecules can coordinate the Cu2+ confirmed by thermodynamic data, which strongly generates the linking of the NCs via the Cu2+ ions in acidic pH, and a parallel fluorescence quenching occurs. In the case of Fe3+, the degree of quenching strongly depends on the metal ion concentration, and it only occurs when the NCs are not able to bind more Fe3+ (~10 µM) on the surface, causing the NCs’ aggregation.}, year = {2024}, eissn = {2079-4991}, orcid-numbers = {Ungor, Ditta Anita/0000-0002-7659-0428; Szatmári, István/0000-0002-8571-5229; Juhász, Ádám/0000-0003-0033-7968; Csapó, Edit/0000-0002-6980-9524} } @article{MTMT:34666945, title = {Synthesis and Study of the Structure–Activity Relationship of Antiproliferative N-Substituted Isosteviol-Based 1,3-Aminoalcohols}, url = {https://m2.mtmt.hu/api/publication/34666945}, author = {Ozsvár, Dániel and Bózsity-Faragó, Noémi and Zupkó, István and Szakonyi, Zsolt}, doi = {10.3390/ph17020262}, journal-iso = {PHARMACEUTICALS-BASE}, journal = {PHARMACEUTICALS}, volume = {17}, unique-id = {34666945}, abstract = {Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were prepared via stereoselective transformations. The acid-catalysed hydrolysis and rearrangement of natural stevioside produced isosteviol, which was transformed into the key intermediate methyl ester. In the next step, an 1,3-aminoalcohol library was prepared by the reductive amination of the intermediate 3-hydroxyaldehyde obtained from isosteviol in a two-step synthesis. To study the effect of the carboxylate ester function at position 4, the free carboxylic acid, benzyl ester and acryloyl ester analogues were prepared as elongated derivatives in comparison with our earlier results in this field. The antiproliferative activity of compounds against human tumour cell lines (A2780, HeLa, MCF-7 and MDA-MB-231) was investigated. In our preliminary study, the 1,3-aminoalcohol function with N-benzyl or (1H-imidazol-1-yl)-propyl substitution and benzyl ester moiety seemed essential for the reliable antiproliferative activity. The results obtained could be a good starting point to further functionalisation towards more efficient antiproliferative diterpenes.}, year = {2024}, eissn = {1424-8247}, orcid-numbers = {Zupkó, István/0000-0003-3243-5300; Szakonyi, Zsolt/0000-0003-2432-8409} } @article{MTMT:34577084, title = {Stereoselective synthesis and antiproliferative activity of allo-gibberic acid-based 1,3-aminoalcohols regioisomers}, url = {https://m2.mtmt.hu/api/publication/34577084}, author = {Khdar, Zein Alabdeen and Le Minh, Tam and Schelz, Zsuzsanna and Zupkó, István and Szakonyi, Zsolt}, doi = {10.1039/D3MD00665D}, journal-iso = {RSC MED CHEM}, journal = {RSC MEDICINAL CHEMISTRY}, volume = {15}, unique-id = {34577084}, abstract = {A new library of allo -gibberic acid-based aminoalcohol regioisomers was synthesised stereoselectively starting from commercially available gibberellic acid, which yields allo -gibberic acid under mild acidic conditions. The successful formation of hydroxymethyl...}, year = {2024}, eissn = {2632-8682}, pages = {874-887}, orcid-numbers = {Le Minh, Tam/0000-0002-8296-887X; Schelz, Zsuzsanna/0000-0002-8519-4830; Zupkó, István/0000-0003-3243-5300; Szakonyi, Zsolt/0000-0003-2432-8409} } @article{MTMT:34535772, title = {High-performance liquid chromatographic enantioseparation of azole analogs of monoterpene lactones and amides focusing on the separation characteristics of polysaccharide-based chiral stationary phases}, url = {https://m2.mtmt.hu/api/publication/34535772}, author = {Németi, Gábor and Berkecz, Róbert and Le Minh, Tam and Szakonyi, Zsolt and Péter, Antal and Ilisz, István}, doi = {10.1016/j.chroma.2024.464660}, journal-iso = {J CHROMATOGR A}, journal = {JOURNAL OF CHROMATOGRAPHY A}, volume = {1717}, unique-id = {34535772}, issn = {0021-9673}, year = {2024}, eissn = {1873-3778}, orcid-numbers = {Németi, Gábor/0000-0001-7312-8353; Berkecz, Róbert/0000-0002-9076-2177; Le Minh, Tam/0000-0002-8296-887X; Szakonyi, Zsolt/0000-0003-2432-8409; Ilisz, István/0000-0001-8282-457X} } @article{MTMT:34502096, title = {Asymmetric transfer hydrogenation of 2,3-diphenylpropenoic acids over heterogeneous palladium catalysts modified by cinchona alkaloids}, url = {https://m2.mtmt.hu/api/publication/34502096}, author = {Szőllősi, György and Resch, Vivien Erzsébet and Kolcsár, Vanessza Judit}, doi = {10.1016/j.jcat.2024.115290}, journal-iso = {J CATAL}, journal = {JOURNAL OF CATALYSIS}, volume = {429}, unique-id = {34502096}, issn = {0021-9517}, year = {2024}, eissn = {1090-2694}, orcid-numbers = {Szőllősi, György/0000-0003-4418-9530; Resch, Vivien Erzsébet/0000-0003-0044-5731} }