TY - GEN AU - Éva, A. Enyedy AU - Kormányosné Pósa, Vivien AU - Safyanova, Inna AU - Mészáros, János Péter AU - Pivarcsik, Tamás AU - Nóra, V. May AU - Spengler, Gabriella AU - Pósa, Szonja Polett AU - Szilárd, Tóth AU - Gergely, Szakács AU - Csuvik, Oszkár AU - Szatmári, István TI - Water-soluble 8-hydroxyquinoline-amino acid hybrids and their interaction with various metal ions: relationship between solution chemistry and cytotoxicity. PY - 2022 UR - https://m2.mtmt.hu/api/publication/35322535 ID - 35322535 LA - English DB - MTMT ER - TY - CONF AU - Shahmohammadi, Sayeh AU - Faragó, Tünde AU - Palkó, Márta AU - Forró, Enikő TI - Green enzymatic strategies for the preparation of enantiomeric carbocyclic beta-amino acid derivatives T2 - GreenCat 2022 Book of Abstracts PY - 2022 PG - 1 UR - https://m2.mtmt.hu/api/publication/33672957 ID - 33672957 LA - English DB - MTMT ER - TY - JOUR AU - Bamou Zahra, Fatima AU - Le Minh, Tam AU - Tayeb, Bizhar Ahmed AU - Senobar Tahaei, Seyyed Ashkan AU - Minorics, Renáta AU - Zupkó, István AU - Szakonyi, Zsolt TI - Antiproliferative Activity of (-)-Isopulegol-based 1,3-Oxazine, 1,3-Thiazine and 2,4-Diaminopyrimidine Derivative JF - CHEMISTRYOPEN J2 - CHEMISTRYOPEN VL - 11 PY - 2022 IS - 10 PG - 11 SN - 2191-1363 DO - 10.1002/open.202200169 UR - https://m2.mtmt.hu/api/publication/33128234 ID - 33128234 AB - A series of novel heterocyclic structures, namely 1,3-oxazines, 1,3-thiazines and 2,4-diaminopyrimidines, were designed and synthesised. The bioassay tests demonstrated that, among these analogues, 2,4-diaminopyridine derivatives showed significant antiproliferative activity against different human cancer cell lines (A2780, SiHa, HeLa, MCF-7 and MDA-MB-231). Pyrimidines substituted with N-2-(p-trifluoromethyl)aniline, in particular, displayed a potent inhibitory effect on the growth of cancer cells. Structure-activity relationships were also studied from the aspects of stereochemistry on the aminodiol moiety as well as exploring the effects of substituents on the pyrimidine scaffold. LA - English DB - MTMT ER - TY - JOUR AU - Khdar, Zein Alabdeen AU - Le Minh, Tam AU - Schelz, Zsuzsanna AU - Zupkó, István AU - Szakonyi, Zsolt TI - Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 23 PY - 2022 IS - 18 PG - 24 SN - 1661-6596 DO - 10.3390/ijms231810366 UR - https://m2.mtmt.hu/api/publication/33087002 ID - 33087002 AB - A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according to literature methods. Epoxidation of key intermediate and subsequent ring-opening of the corresponding epoxide with different nucleophiles resulted in N-substituted aminodiols. The regioselective ring closure of N-benzyl-substituted aminodiol with formaldehyde was also investigated. All aminodiol derivatives were well characterized using modern spectroscopic techniques and evaluated for their antiproliferative activity against a panel of human cancer cell lines. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol systems. The results indicated that aminodiols containing aromatic rings on their nitrogen substituents displayed significant cytotoxic effects. Among these agents, N-naphthylmethyl-substituted aminodiols were found to be the most potent candidates in this series. One of these molecules exhibited a modest cancer selectivity determined by non-cancerous fibroblast cells. A docking study was also made to exploit the observed results. LA - English DB - MTMT ER - TY - JOUR AU - Forró, Enikő AU - Fülöp, Ferenc TI - Enzymatic Strategies for the Preparation of Pharmaceutically Important Amino Acids through Hydrolysis of Amino Carboxylic Esters and Lactams JF - CURRENT MEDICINAL CHEMISTRY J2 - CURR MED CHEM VL - 29 PY - 2022 IS - 41 SP - 6218 EP - 6227 PG - 10 SN - 0929-8673 DO - 10.2174/0929867329666220718123153 UR - https://m2.mtmt.hu/api/publication/33025006 ID - 33025006 N1 - Funding Agency and Grant Number: Hungarian Scientific Research Council (OTKA) [K129049]; Ministry of National Economy, National Research, Development and Innovation Office (GINOP) [2.3.2-15-2016-00014]; ITM NKFIA [TKP2021-EGA-32] Funding text: The authors thank the Hungarian Scientific Research Council (OTKA, K129049) and the Ministry of National Economy, National Research, Development and Innovation Office (GINOP, 2.3.2-15-2016-00014) and ITM NKFIA TKP2021-EGA-32 for financial support. LA - English DB - MTMT ER - TY - JOUR AU - Pape, Veronika AU - Kovács, Hajnal Anna AU - Szatmári, István AU - Ugrai, Imre AU - Szikora, Bence AU - Kacskovics, Imre AU - May, Zoltán AU - Szoboszlai, Norbert AU - Sirokmány, Gábor AU - Geiszt, Miklós TI - Measuring peroxidasin activity in live cells using bromide addition for signal amplification JF - REDOX BIOLOGY J2 - REDOX BIOL VL - 54 PY - 2022 PG - 14 SN - 2213-2317 DO - 10.1016/j.redox.2022.102385 UR - https://m2.mtmt.hu/api/publication/32918558 ID - 32918558 N1 - Department of Physiology, Semmelweis University, Faculty of Medicine, Tűzoltó utca 37-47, Budapest, H-1094, Hungary Institute of Pharmaceutical Chemistry and Stereochemistry Research Group of Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary ImmunoGenes Ltd., Budakeszi, Hungary Research Centre for Natural Sciences, Eötvös Loránd Research Network, Magyar Tudósok körútja 2, Budapest, H-1117, Hungary Institute of Chemistry, Eötvös Loránd University, Pázmány Péter sétány 1/A, Budapest, H-1117, Hungary Export Date: 20 July 2022 Correspondence Address: Geiszt, M.; Department of Physiology, Tűzoltó utca 37-47, Hungary; email: geiszt.miklos@med.semmelweis-univ.hu Correspondence Address: Pape, V.F.S.; Department of Physiology, Tűzoltó utca 37-47, Hungary; email: veronika.pape@med.semmelweis-univ.hu LA - English DB - MTMT ER - TY - JOUR AU - Lőrinczi, Bálint AU - Simon, Péter AU - Szatmári, István TI - Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases JF - INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES J2 - INT J MOL SCI VL - 23 PY - 2022 IS - 13 PG - 13 SN - 1661-6596 DO - 10.3390/ijms23137152 UR - https://m2.mtmt.hu/api/publication/32911266 ID - 32911266 N1 - Export Date: 11 April 2023 Correspondence Address: Szatmári, I.; Institute of Pharmaceutical Chemistry, Eötvös u. 6, Hungary; email: szatmari.istvan@szte.hu Chemicals/CAS: Indoles; Mannich Bases Funding details: TKP-2021-EGA-32 Funding details: Gedeon Richter Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding text 1: The authors’ thanks are due to the Hungarian Research Foundation (OTKA No. K-138871) and the Ministry of Human Capacities, Hungary grant, TKP-2021-EGA-32, and to the Gedeon Richter Plc. Centenarial Foundation. The authors would also thank Rita Ambrus (Institute of Pharmaceutical Technology and Regulatory Affairs, University of Szeged) for the FTIR investigations. Funding text 2: Acknowledgments: The authors’ thanks are due to the Hungarian Research Foundation (OTKA No. K-138871) and the Ministry of Human Capacities, Hungary grant, TKP-2021-EGA-32, and to the Gedeon Richter Plc. Centenarial Foundation. The authors would also thank Rita Ambrus (Institute of Pharmaceutical Technology and Regulatory Affairs, University of Szeged) for the FTIR investigations. LA - English DB - MTMT ER - TY - JOUR AU - Pape, Veronika AU - Palkó, Roberta AU - Tóth, Szilárd AU - Szabó, Miklós J. AU - Sessler, Judit AU - Dormán, György AU - Enyedy, Éva Anna AU - Soós, Tibor AU - Szatmári, István AU - Szakács, Gergely TI - Structure–Activity Relationships of 8-Hydroxyquinoline-Derived Mannich Bases with Tertiary Amines Targeting Multidrug-Resistant Cancer JF - JOURNAL OF MEDICINAL CHEMISTRY J2 - J MED CHEM VL - 65 PY - 2022 IS - 11 SP - 7729 EP - 7745 PG - 17 SN - 0022-2623 DO - 10.1021/acs.jmedchem.2c00076 UR - https://m2.mtmt.hu/api/publication/32843044 ID - 32843044 LA - English DB - MTMT ER - TY - JOUR AU - Hegedűs, Dóra AU - Szemerédi, Nikoletta AU - Spengler, Gabriella AU - Szatmári, István TI - Application of partially aromatic ortho-quionone-methides for the synthesis of novel naphthoxazines with improved antibacterial activity JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 237 PY - 2022 PG - 8 SN - 0223-5234 DO - 10.1016/j.ejmech.2022.114391 UR - https://m2.mtmt.hu/api/publication/32790854 ID - 32790854 N1 - Institute of Pharmaceutical Chemistry and Research Group for Stereochemistry, Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, Szeged, H-6720, Hungary Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary Excellence Center, Eötvös u. 6, Szeged, H-6720, Hungary Department of Medical Microbiology, Albert Szent-Györgyi Health Center and Albert Szent-Györgyi Medical School, University of Szeged, Semmelweis utca 6, Szeged, 6725, Hungary Cited By :1 Export Date: 6 April 2023 CODEN: EJMCA Correspondence Address: Szatmári, I.; Institute of Pharmaceutical Chemistry and Research Group for Stereochemistry, Eötvös u. 6, Hungary; email: szatmari.istvan@szte.hu Chemicals/CAS: reserpine, 50-55-5, 8001-95-4; amino acid, 65072-01-7; imine, 13774-92-0; Amino Acids; Anti-Bacterial Agents; Imines Funding details: EFOP-3.6.3-VEKOP-16-2017-00009, TKP-2021-EGA-32 Funding details: Hungarian Scientific Research Fund, OTKA, K-138871 Funding text 1: The authors' thanks are due to the Hungarian Research Foundation (OTKA No. K-138871 ) and the Ministry of Human Capacities , Hungary grant, TKP-2021-EGA-32 . N.S. was supported by the project EFOP-3.6.3-VEKOP-16-2017-00009 (Hungary). Funding text 2: To start our investigation on the formation of partially aromatic ortho-quinone methides (o-QM) via [4 + 2] cycloaddition, 2-naphthol-substituted glycine precursor 3 was synthesised. Accordingly, 2-naphthol (1) and morpholine (2) were reacted in the presence of ethyl glyoxylate as an aldehyde component. In one of our previous works, it was found, that hydroxynaphthyl-substituted glycine derivatives can be generated from 2- or 1-naphthol, benzyl carbamate and glyoxylic acid via the modified Mannich reaction. We pointed out that in the presence of p-toluenesulfonic acid the reaction yield increased. Furthermore, the absolute configuration of the enantiomers was determined by circular dichroism (CD) analysis supported by TDDFT calculations [21]. Moreover, in the case of glycine ester analogues substituted with 2- or 1-naphthol, the separation of enantiomers was achieved via HPLC measurements and a systematic influence was observed between the character of the ester function and HPLC parameters [22]. In order to form functionalised aminonaphthol derivatives, morpholine (2) as stable cyclic secondary amine was selected as substrate in the reactions. The crude reaction mixtures formed under microwave irradiation in 30 min at 80 ?C and in 30 min at 100 ?C in toluene were examined by 1H NMR measurements. It is interesting to note that using conventional heating, the formation of the desired product 3 could not be detected (Scheme 1).The authors' thanks are due to the Hungarian Research Foundation (OTKA No. K-138871) and the Ministry of Human Capacities, Hungary grant, TKP-2021-EGA-32. N.S. was supported by the project EFOP-3.6.3-VEKOP-16-2017-00009 (Hungary). LA - English DB - MTMT ER - TY - JOUR AU - Shahmohammadi, Sayeh AU - Faragó, Tünde AU - Palkó, Márta AU - Forró, Enikő TI - Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis JF - MOLECULES J2 - MOLECULES VL - 27 PY - 2022 IS - 8 PG - 11 SN - 1431-5157 DO - 10.3390/molecules27082600 UR - https://m2.mtmt.hu/api/publication/32787510 ID - 32787510 N1 - Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, Szeged, H-6720, Hungary MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Szeged, H-6720, Hungary Export Date: 4 June 2023 CODEN: MOLEF Correspondence Address: Forró, E.; Institute of Pharmaceutical Chemistry, Hungary; email: forro.eniko@szte.hu Chemicals/CAS: amino acid, 65072-01-7; Amino Acids; Esters; Fungal Proteins; Solvents Funding details: 2.3.2-15-2016-00014, EFOP 3.6.3-VEKOP-16-2017-00009 Funding details: Hungarian Scientific Research Fund, OTKA, K129049, K138871 Funding details: National Research, Development and Innovation Office Funding text 1: Funding: The authors thank the Hungarian Scientific Research Council (OTKA, K129049 and K138871) and the Ministry of National Economy, National Research, Development and Innovation Office (GINOP, 2.3.2-15-2016-00014) and (EFOP 3.6.3-VEKOP-16-2017-00009) for financial support. LA - English DB - MTMT ER -