TY - JOUR AU - Ábrányi-Balogh, Péter AU - Molnárné Samu, Erika AU - Pánczél, János K. AU - Benkő, Zoltán AU - Simig, Gyula AU - Volk, Balázs TI - Computational Studies on the Diastereospecific Lithium Variant of Oppenauer Oxidation of a Tofisopam Intermediate JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM PY - 2024 PG - 6 SN - 0022-3263 DO - 10.1021/acs.joc.3c02660 UR - https://m2.mtmt.hu/api/publication/34778896 ID - 34778896 N1 - Medicinal Chemistry Research Group, Research Centre for Natural Sciences, Magyar tudósok krt. 2, Budapest, H-1117, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, Budapest, H-1111, Hungary National Laboratory for Drug Research and Development, Magyar tudósok krt. 2, Budapest, H-1117, Hungary Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., Budapest, H-1475, Hungary Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szt. Gellért tér 4, Budapest, H-1111, Hungary Export Date: 12 April 2024 CODEN: JOCEA Correspondence Address: Ábrányi-Balogh, P.; Medicinal Chemistry Research Group, Magyar tudósok krt. 2, Hungary; email: abranyi-balogh.peter@ttk.hu Correspondence Address: Volk, B.; Directorate of Drug Substance Development, Hungary; email: volk.balazs@egis.hu LA - English DB - MTMT ER - TY - JOUR AU - Keeley, Aaron Brian AU - Kopranovic, Aleksandra AU - Di Lorenzo, Vincenzo AU - Ábrányi-Balogh, Péter AU - Jänsch, Niklas AU - Lai, Linh N. AU - Petri, László AU - Orgován, Zoltán AU - Pölöske, Daniel AU - Orlova, Anna AU - Németh, András György AU - Desczyk, Charlotte AU - Imre, Timea AU - Bajusz, Dávid AU - Moriggl, Richard AU - Meyer-Almes, Franz-Josef AU - Keserű, György Miklós TI - Electrophilic MiniFrags Revealed Unprecedented Binding Sites for Covalent HDAC8 Inhibitors JF - JOURNAL OF MEDICINAL CHEMISTRY J2 - J MED CHEM VL - 67 PY - 2024 IS - 1 SP - 572 EP - 585 PG - 14 SN - 0022-2623 DO - 10.1021/acs.jmedchem.3c01779 UR - https://m2.mtmt.hu/api/publication/34445373 ID - 34445373 N1 - Medicinal Chemistry Research Group, Research Centre for Natural Sciences, Magyar tudósok krt 2, Budapest, H-1117, Hungary Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Müegyetem rkp. 3., Budapest, H-1111, Hungary National Laboratory for Drug Research and Development, Budapest, H-1117, Hungary Department of Chemical Engineering and Biotechnology, University of Applied Sciences Darmstadt, Haardtring 100, Darmstadt, 64295, Germany Institute of Animal Breeding and Genetics, University of Veterinary Medicine, Vienna, 1210, Austria MS Metabolomics Research Group, Research Centre for Natural Sciences, Magyar tudósok krt 2, Budapest, H-1117, Hungary Export Date: 14 March 2024 CODEN: JMCMA Correspondence Address: Meyer-Almes, F.-J.; Department of Chemical Engineering and Biotechnology, Haardtring 100, Germany; email: franz-josef.meyer-almes@h-da.de Correspondence Address: Keserü, G.M.; Medicinal Chemistry Research Group, Magyar tudósok krt 2, Hungary; email: keseru.gyorgy@ttk.hu AB - Screening of ultra-low-molecular weight ligands (MiniFrags) successfully identified viable chemical starting points for a variety of drug targets. Here we report the electrophilic analogues of MiniFrags that allow the mapping of potential binding sites for covalent inhibitors by biochemical screening and mass spectrometry. Small electrophilic heterocycles and their N-quaternized analogues were first characterized in the glutathione assay to analyze their electrophilic reactivity. Next, the library was used for systematic mapping of potential covalent binding sites available in human histone deacetylase 8 (HDAC8). The covalent labeling of HDAC8 cysteines has been proven by tandem mass spectrometry measurements, and the observations were explained by mutating HDAC8 cysteines. As a result, screening of electrophilic MiniFrags identified three potential binding sites suitable for the development of allosteric covalent HDAC8 inhibitors. One of the hit fragments was merged with a known HDAC8 inhibitor fragment using different linkers, and the linker length was optimized to result in a lead-like covalent inhibitor. © 2023 The Authors. Published by American Chemical Society LA - English DB - MTMT ER - TY - JOUR AU - Csorba, Noémi AU - Ábrányi-Balogh, Péter AU - Keserű, György Miklós TI - Covalent fragment approaches targeting non-cysteine residues JF - TRENDS IN PHARMACOLOGICAL SCIENCES J2 - TRENDS PHARMACOL SCI VL - 44 PY - 2023 IS - 11 SP - 802 EP - 816 PG - 15 SN - 0165-6147 DO - 10.1016/j.tips.2023.08.014 UR - https://m2.mtmt.hu/api/publication/34160949 ID - 34160949 N1 - Export Date: 6 October 2023 CODEN: TPHSD Correspondence Address: Keserű, G.M.; Medicinal Chemistry Research Group, Magyar tudósok krt. 2, 1117, Hungary; email: keseru.gyorgy@ttk.hu LA - English DB - MTMT ER - TY - JOUR AU - Orgován, Zoltán AU - Péczka, Nikolett AU - Petri, László AU - Ábrányi-Balogh, Péter AU - Randelovic, Ivan AU - Tóth, Szilárd AU - Szakács, Gergely AU - Nyíri, Kinga AU - Vértessy, Beáta (Grolmuszné) AU - Pálfy, Gyula AU - Vida, István AU - Perczel, András AU - Tóvári, József AU - Keserű, György Miklós TI - Covalent fragment mapping of KRasG12C revealed novel chemotypes with in vivo potency JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 250 PY - 2023 PG - 7 SN - 0223-5234 DO - 10.1016/j.ejmech.2023.115212 UR - https://m2.mtmt.hu/api/publication/33647485 ID - 33647485 N1 - Medicinal Chemistry Research Group, Research Centre for Natural Sciences, and National Drug Discovery and Development Laboratory, Budapest, Hungary Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Budapest, Hungary KINETO Lab Ltd, Budapest, Hungary Institute of Enzymology, Research Centre for Natural Sciences, Budapest, Hungary Department of Applied Biotechnology and Food Science, Budapest University of Technology and Economics, Hungary Laboratory of Structural Chemistry and Biology, Eötvös Loránd University, Budapest, Hungary MTA-ELTE Protein Modelling Research Group, Eötvös Loránd University, Budapest, Hungary Department of Experimental Pharmacology and the National Tumor Biology Laboratory, National Institute of Oncology, Budapest, Hungary CODEN: EJMCA Correspondence Address: Keserű, G.M.; Medicinal Chemistry Research Group, 2 Magyar tudósok kӧrútja, Hungary; email: keseru.gyorgy@ttk.hu AB - G12C mutant KRas is considered druggable by allele-specific covalent inhibitors due to the nucleophilic character of the oncogenic mutant cysteine at position 12. Discovery of these inhibitors requires the optimization of both covalent and noncovalent interactions. Here, we report covalent fragment screening of our electrophilic fragment library of diverse non-covalent scaffolds equipped with 40 different electrophilic functionalities to identify fragments as suitable starting points targeting Cys12. Screening the library against KRasG12C using Ellman's free thiol assay, followed by protein NMR and cell viability assays, resulted in two potential inhibitor chemotypes. Characterization of these scaffolds in in vitro cellular- and in vivo xenograft models revealed them as promising starting points for covalent drug discovery programs. LA - English DB - MTMT ER - TY - JOUR AU - Petri, László AU - Ábrányi-Balogh, Péter AU - Csorba, Noémi AU - Keeley, Aaron Brian AU - Simon, József AU - Randelovic, Ivan AU - Tóvári, József AU - Schlosser, Gitta (Vácziné) AU - Szabó, Dániel AU - Drahos, László AU - Keserű, György Miklós TI - Activation-Free Sulfonyl Fluoride Probes for Fragment Screening JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 7 PG - 17 SN - 1420-3049 DO - 10.3390/molecules28073042 UR - https://m2.mtmt.hu/api/publication/33729477 ID - 33729477 N1 - Medicinal Chemistry Research Group, Research Centre for Natural Sciences, Magyar Tudósok Krt. 2, Budapest, 1117, Hungary National Laboratory for Drug Research and Development, Research Centre for Natural Sciences, Magyar Tudósok Krt. 2, Budapest, 1117, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, Budapest, 1111, Hungary Research Centre for Natural Sciences, MS Metabolomics Research Group, Magyar Tudósok Krt. 2, Budapest, 1117, Hungary KINETO Lab Ltd, Zápor u. 55, Budapest, 1032, Hungary Department of Experimental Pharmacology and National Tumor Biology Laboratory, National Institute of Oncology, POB 21, Budapest, 1525, Hungary MTA-ELTE Lendület Ion Mobility Mass Spectrometry Research Group, Institute of Chemistry, ELTE Eötvös Loránd University, Pázmány Péter Sétány 1/A, Budapest, 1117, Hungary MS Proteomics Research Group, Research Centre for Natural Sciences, Magyar Tudósok Krt. 2, Budapest, 1117, Hungary Cited By :3 Export Date: 13 March 2024 CODEN: MOLEF Correspondence Address: Keserű, G.M.; Medicinal Chemistry Research Group, Magyar Tudósok Krt. 2, Hungary; email: keseru.gyorgy@ttk.hu AB - SuFEx chemistry is based on the unique reactivity of the sulfonyl fluoride group with a range of nucleophiles. Accordingly, sulfonyl fluorides label multiple nucleophilic amino acid residues, making these reagents popular in both chemical biology and medicinal chemistry applications. The reactivity of sulfonyl fluorides nominates this warhead chemotype as a candidate for an external, activation-free general labelling tag. Here, we report the synthesis and characterization of a small sulfonyl fluoride library that yielded the 3-carboxybenzenesulfonyl fluoride warhead for tagging tractable targets at nucleophilic residues. Based on these results, we propose that coupling diverse fragments to this warhead would result in a library of sulfonyl fluoride bits (SuFBits), available for screening against protein targets. SuFBits will label the target if it binds to the core fragment, which facilitates the identification of weak fragments by mass spectrometry. LA - English DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Chiovini, Balázs AU - Müller, Dalma AU - Tóth, Estilla Zsófia AU - Fülöp, Anna AU - Ábrányi-Balogh, Péter AU - Wittner, Lucia AU - Várady, György AU - Farkas, Ödön AU - Turczel, Gábor AU - Katona, Gergely AU - Győrffy, Balázs AU - Keserű, György Miklós AU - Mucsi, Zoltán AU - Rózsa J., Balázs AU - Kovács, Ervin TI - Synthesis and Application of Two-Photon Active Fluorescent Rhodol Dyes for Antibody Conjugation and In Vitro Cell Imaging JF - ACS OMEGA J2 - ACS OMEGA VL - 8 PY - 2023 IS - 25 SP - 22836 EP - 22843 PG - 8 SN - 2470-1343 DO - 10.1021/acsomega.3c01796 UR - https://m2.mtmt.hu/api/publication/34015800 ID - 34015800 LA - English DB - MTMT ER - TY - JOUR AU - Szepesi Kovács, Dénes AU - Kontra, Bence AU - Chiovini, Balázs AU - Müller, Dalma AU - Tóth, Estilla Zsófia AU - Ábrányi-Balogh, Péter AU - Wittner, Lucia AU - Várady, György AU - Turczel, Gábor AU - Farkas, Ödön AU - Owen, Michael Christopher AU - Katona, Gergely AU - Győrffy, Balázs AU - Keserű, György Miklós AU - Mucsi, Zoltán AU - Rózsa J., Balázs AU - Kovács, Ervin TI - Effective Synthesis, Development and Application of a Highly Fluorescent Cyanine Dye for Antibody Conjugation and Microscopy Imaging JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 21 PY - 2023 IS - 44 SP - 8829 EP - 8836 PG - 8 SN - 1477-0520 DO - 10.1039/D3OB01471A UR - https://m2.mtmt.hu/api/publication/34205650 ID - 34205650 AB - An asymmetric cyanine-type fluorescent dye was designed and synthesized via a versatile, multi-step process, aiming to conjugate with an Her2+ receptor specific antibody by an azide-alkyne click reaction. The aromaticity and the excitation and relaxation energetics of the fluorophore were characterized by computational methods. The synthesized dye exhibited excellent fluorescence properties for confocal microscopy, offering efficient applicability in in vitro imaging due to its merits such as a high molar absorption coefficient (36 816 M-1 cm-1), excellent brightness, optimal wavelength (627 nm), larger Stokes shift (26 nm) and appropriate photostability compared to cyanines. The conjugated cyanine-trastuzumab was constructed via an effective, metal-free, strain-promoted azide-alkyne click reaction leading to a regulated number of dyes being conjugated. This novel cyanine-labelled antibody was successfully applied for in vitro confocal imaging and flow cytometry of Her2+ tumor cells. An azido cyanine dye was synthesized and characterized by computational and experimental techniques and applied in tumor cell imaging. LA - English DB - MTMT ER - TY - CHAP AU - Ábrányi-Balogh, Péter AU - Keserű, György Miklós ED - Xudong, Yao ED - Michael, Bryant Smith TI - Warheads for designing covalent inhibitors and chemical probes T2 - Advances in Chemical Proteomics PB - Elsevier CY - Amsterdam SN - 9780128214350 PY - 2022 SP - 47 EP - 73 PG - 27 DO - 10.1016/B978-0-12-821433-6.00007-6 UR - https://m2.mtmt.hu/api/publication/33650196 ID - 33650196 AB - Covalent labeling of amino acid residues has emerged as a significant protocol in both medicinal chemistry and chemical biology applications in the last decades. In this chapter, we focus on those functional groups, so called warheads that form covalent bonds with the targeted amino acid side chains in proteins. We discuss the residues targeted by more than a hundred functional groups, together with their reported selectivity, reactivity and labeling mechanism. The collection of relevant literature is up to date until first May 2020. From this compilation one can conclude that there are available targets with only a few reported warheads, thus the discovery of new chemistries could contribute to the suitable labeling with a wider selection of functional groups. In addition, this wide landscape of warheads enables choosing the appropriate one and tailoring the functionality to the amino acid targeted as an efficient and selective methodology. © 2022 Elsevier Inc. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Ábrányi-Balogh, Péter AU - Keeley, Aaron AU - Ferenczy, György AU - Petri, László AU - Imre, Timea AU - Grabrijan, Katarina AU - Hrast, Martina AU - Knez, Damijan AU - Ilaš, Janez AU - Gobec, Stanislav AU - Keserű, György Miklós TI - Next-Generation Heterocyclic Electrophiles as Small-Molecule Covalent MurA Inhibitors JF - PHARMACEUTICALS J2 - PHARMACEUTICALS-BASE VL - 15 PY - 2022 IS - 12 SN - 1424-8247 DO - 10.3390/ph15121484 UR - https://m2.mtmt.hu/api/publication/33298396 ID - 33298396 AB - Heterocyclic electrophiles as small covalent fragments showed promising inhibitory activity on the antibacterial target MurA (UDP-N-acetylglucosamine 1-carboxyvinyltransferase, EC:2.5.1.7). Here, we report the second generation of heterocyclic electrophiles: the quaternized analogue of the heterocyclic covalent fragment library with improved reactivity and MurA inhibitory potency. Quantum chemical reaction barrier calculations, GSH (L-glutathione) reactivity assay, and thrombin counter screen were also used to demonstrate and explain the improved reactivity and selectivity of the N-methylated heterocycles and to compare the two generations of heterocyclic electrophiles. LA - English DB - MTMT ER - TY - JOUR AU - Ábrányi-Balogh, Péter AU - Harsági, Nikoletta AU - Drahos, László AU - Keglevich, György TI - A Study on the Direct Esterification of Monoalkylphosphates and Dialkylphosphates; The Conversion of the Latter Species to Trialkylphosphates by Alkylating Esterification JF - MOLECULES J2 - MOLECULES VL - 27 PY - 2022 IS - 15 PG - 9 SN - 1420-3049 DO - 10.3390/molecules27154674 UR - https://m2.mtmt.hu/api/publication/33050385 ID - 33050385 N1 - Medicinal Chemistry Research Group, Research Centre for Natural SciencesBudapest 1117, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology and EconomicsBudapest 1521, Hungary MS Proteomics Research Group, Research Centre for Natural SciencesBudapest 1117, Hungary Export Date: 18 August 2022 AB - The microwave (MW)-assisted direct esterification of certain P-acids is a green method. Quantum chemical calculations revealed that the activation enthalpy (ΔH#) for the exothermic monoalkylphosphate → dialkylphosphate transformation was on the average 156.6 kJ mol−1, while ΔH# for the dialkylphosphate → trialkylphosphate conversion was somewhat higher, 171.2 kJ mol−1, and the energetics of the elemental steps of this esterification was less favorable. The direct monoesterification may be performed on MW irradiation in the presence of a suitable ionic liquid additive. However, the second step, with the less favorable energetics as a whole, could not be promoted by MWs. Hence, dialkylphosphates had to be converted to triesters by another method that was alkylation. In this way, it was also possible to synthesize triesters with different alkyl groups. Eventually a green, P-chloride free MW-promoted two-step method was elaborated for the synthesis of phosphate triesters. LA - English DB - MTMT ER - TY - JOUR AU - Grabrijan, K. AU - Hrast, M. AU - Proj, M. AU - Dolšak, A. AU - Zdovc, I. AU - Imre, Timea AU - Petri, László AU - Ábrányi-Balogh, Péter AU - Keserű, György Miklós AU - Gobec, S. TI - Covalent inhibitors of bacterial peptidoglycan biosynthesis enzyme MurA with chloroacetamide warhead JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 243 PY - 2022 PG - 15 SN - 0223-5234 DO - 10.1016/j.ejmech.2022.114752 UR - https://m2.mtmt.hu/api/publication/33126961 ID - 33126961 N1 - Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, Ljubljana, 1000, Slovenia Veterinary Faculty, University of Ljubljana, Gerbičeva 60, Ljubljana, 1000, Slovenia Medicinal Chemistry Research Group, Research Centre for Natural Sciences, Magyar tudósok krt. 2, Budapest, H-1117, Hungary MS Proteomics Research Group, Research Centre for Natural Sciences, Magyar tudósok krt. 2, Budapest, H-1117, Hungary Department of Organic Chemistry and Technology, Budapest University of Technology, Szt. Gellért tér 4., Budapest, H-1117, Hungary Export Date: 5 October 2022 CODEN: EJMCA Correspondence Address: Gobec, S.; Faculty of Pharmacy, Aškerčeva 7, Slovenia; email: stanislav.gobec@ffa.uni-lj.si LA - English DB - MTMT ER - TY - JOUR AU - Harsági, Nikoletta AU - Kiss, Nóra Zsuzsa AU - Ábrányi-Balogh, Péter AU - Keglevich, György TI - Microwave-assisted esterification of P-acids JF - PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS J2 - PHOSPHOR SULFUR SIL REL ELEM VL - 197 PY - 2022 IS - 5-6 SP - 529 EP - 531 PG - 3 SN - 1042-6507 DO - 10.1080/10426507.2021.1990925 UR - https://m2.mtmt.hu/api/publication/32518471 ID - 32518471 N1 - This project was supported by the National Research, Development and Innovation Office (K134318). AB - The possibilities for the preparation of dialky phenylphosphonates were evaluated. On the one hand, the oxidation of phenyl-H-phosphinates gave the corresponding phenylphosphonic acid monoesters. On the other hand, phenylphosphonates may be prepared by MW-assisted direct esterification of phenylphosphonic acid. The reaction with alcohols was performed under MW irradiation in the presence of an ionic liquid as the catalyst. The second ester function was established by alkylating esterification carried out with alkyl halides in the presence of triethylamine under MW conditions. LA - English DB - MTMT ER - TY - JOUR AU - Koványiné Lax, Györgyi AU - Hargitai, Csilla Eszter AU - Ábrányi-Balogh, Péter AU - Nagy, Tamás AU - Tóth, Gábor AU - Garádi, Zsófia AU - Németh, Gábor AU - Pandur, Angéla AU - Horváth, Simon AU - Dancsó, András AU - Simig, Gyula AU - Volk, Balázs TI - Experimental and computational study of BF3-catalyzed transformations of ortho-(pivaloylaminomethyl)benzaldehydes: an unexpected difference from TFA catalysis JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 20 PY - 2022 IS - 9 SP - 1933 EP - 1944 PG - 12 SN - 1477-0520 DO - 10.1039/D1OB02308J UR - https://m2.mtmt.hu/api/publication/32672327 ID - 32672327 N1 - Funding Agency and Grant Number: Ministry for Innovation and Technology - National Research, Development and Innovation Fund [KDP-1007075] Funding text: The authors are grateful to Ms Viktoria Garbacz for carrying out several experiments and to Dr Eva Sipos for supervising these. We also thank to Ms Monika Mezovari for IR and HRMS, to Mr Peter Kovago for NMR measurements, to Dr Maria Toth-Lauritz and Ms Dora Nemeth for HRMS measurements, furthermore to Ms Agnes Turcsik, Ms Beata Makai and Ms Zita Kasko-Bisztriczki for elemental analysis tests. The manuscript was prepared with the professional support of the Doctoral Student Scholarship Program of the Co-operative Doctoral Program of the Ministry for Innovation and Technology, financed by the National Research, Development and Innovation Fund (KDP-1007075, Z. G.). LA - English DB - MTMT ER - TY - JOUR AU - Mayer, Szabolcs AU - Nagy, Nóra AU - Keglevich, Péter AU - Ábrányi-Balogh, Péter AU - Hazai, László TI - Sejtosztódásgátló hatású vindolin- és flavonoidszármazékok előállítása JF - MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-) J2 - MAGY KÉM FOLY KÉM KÖZL VL - 128 PY - 2022 IS - 3-4 SP - 137 EP - 142 PG - 6 SN - 1418-9933 DO - 10.24100/MKF.2022.03-4.137 UR - https://m2.mtmt.hu/api/publication/33543663 ID - 33543663 N1 - "Mayer Szabolcs PhD értekezéséhez kapcsolódó tézisfüzet alapján készült." LA - Hungarian DB - MTMT ER - TY - JOUR AU - Németh, András György AU - Szabó, Renáta AU - Németh, Krisztina AU - Keserű, György Miklós AU - Ábrányi-Balogh, Péter TI - A stepwise one-pot synthesis of aliphatic thiols and their derivatives from acrylamides and sulfur JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 20 PY - 2022 SP - 4361 EP - 4368 PG - 8 SN - 1477-0520 DO - 10.1039/D2OB00512C UR - https://m2.mtmt.hu/api/publication/32832471 ID - 32832471 N1 - Funding Agency and Grant Number: Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences Funding text: P. a-B. is grateful for the support of the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences. R. Sz. is grateful for the support of uNKP-21-2-II-BME-276 grant. AB - Elemental sulfur enables the convenient formation of C–S bonds and the direct incoporation of S–S bonds. The reactivity of easily accessible electron deficient alkenes towards sulfur, however, is barely disclosed. Herein, we investigated the reactivity of acrylamides with sulfur and eventually developed a new pseudo-multicomponent reaction for the preparation of polysulfides. Sequential one-pot reduction led to diversely substituted thiols. Additional third stage one-pot modifications provided thioethers, unsymmetric disulfide and thioester. LA - English DB - MTMT ER - TY - JOUR AU - Péczka, Nikolett AU - Orgován, Zoltán AU - Ábrányi-Balogh, Péter AU - Keserű, György Miklós TI - Electrophilic warheads in covalent drug discovery: an overview JF - EXPERT OPINION ON DRUG DISCOVERY J2 - EXPERT OPIN DRUG DIS VL - 17 PY - 2022 SP - 413 EP - 422 PG - 10 SN - 1746-0441 DO - 10.1080/17460441.2022.2034783 UR - https://m2.mtmt.hu/api/publication/32756662 ID - 32756662 N1 - CAplus AN 2022:310212; MEDLINE PMID: 35129005 (Journal; General Review; Article); LA - English DB - MTMT ER - TY - JOUR AU - Petri, László AU - Ábrányi-Balogh, Péter AU - Vagrys, Darius AU - Imre, Timea AU - Varró, Nikolett AU - Mándity, István AU - Rácz, Anita AU - Wittner, Lucia AU - Tóth, Kinga AU - Tóth, Estilla Zsófia AU - Juhász, Tünde AU - Davis, Ben AU - Keserű, György Miklós TI - A covalent strategy to target intrinsically disordered proteins: Discovery of novel tau aggregation inhibitors JF - EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY J2 - EUR J MED CHEM VL - 231 PY - 2022 PG - 13 SN - 0223-5234 DO - 10.1016/j.ejmech.2022.114163 UR - https://m2.mtmt.hu/api/publication/32649994 ID - 32649994 LA - English DB - MTMT ER - TY - JOUR AU - Ábrányi-Balogh, Péter AU - Greiner, István AU - Keglevich, György TI - A Mechanistic Study on the Formation of Dronic Acids JF - MOLECULES J2 - MOLECULES VL - 26 PY - 2021 IS - 24 PG - 11 SN - 1420-3049 DO - 10.3390/molecules26247587 UR - https://m2.mtmt.hu/api/publication/32557263 ID - 32557263 N1 - Export Date: 3 January 2022 CODEN: MOLEF Correspondence Address: Ábrányi-Balogh, P.; Research Centre for Natural Sciences, Hungary; email: abranyi-balogh.peter@ttk.mta.hu Correspondence Address: Keglevich, G.; Department of Organic Chemistry and Technology, Hungary; email: keglevich.gyorgy@vbk.bme.hu AB - Dronic acid derivatives, important drugs against bone diseases, may be synthesized from the corresponding substituted acetic acid either by reaction with phosphorus trichloride in methanesulfonic acid as the solvent or by using also phosphorous acid as the P-reactant if sulfolane is applied as the medium. The energetics of the two protocols were evaluated by high-level quantum chemical calculations on the formation of fenidronic acid and benzidronic acid. The second option, involving (HO)2P-O-PCl2 as the nucleophile, was found to be more favorable over the first variation, comprising Cl2P-O-SO2Me as the real reagent, especially for the case of benzidronate. LA - English DB - MTMT ER - TY - JOUR AU - Deák, Andrea Beáta AU - Jobbágy, Csaba AU - Demeter, Attila AU - Čelko, Ladislav AU - Cihlář, Jaroslav AU - Szabó, Pál Tamás AU - Ábrányi-Balogh, Péter AU - Crawford, Deborah E. AU - Virieux, David AU - Colacino, Evelina TI - Mechanochemical synthesis of mononuclear gold( i ) halide complexes of diphosphine ligands with tuneable luminescent properties JF - JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS J2 - J CHEM SOC DALTON TRANS VL - 50 PY - 2021 IS - 38 SP - 13337 EP - 13344 PG - 8 SN - 1472-7773 DO - 10.1039/D1DT01751A UR - https://m2.mtmt.hu/api/publication/32234667 ID - 32234667 N1 - Supramolecular Chemistry Research Group, Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Eötvös Loránd Research Network (ELKH), Magyar Tudósok körútja 2, Budapest, 1117, Hungary Renewable Energy Research Group, Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Eötvös Loránd Research Network (ELKH), Magyar Tudósok körútja 2, Budapest, 1117, Hungary Central European Institute of Technology, Brno University of Technology, Purkyňova 123, Brno, 61200, Czech Republic Centre for Structure Study, Research Centre for Natural Sciences, Eötvös Loránd Research Network (ELKH), 1117 Budapest, Magyar Tudósok körútja 2, Hungary Medicinal Chemistry Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Eötvös Loránd Research Network (ELKH), 1117 Budapest, Magyar Tudósok körútja 2, Hungary School of Chemistry and Biosciences, University of Bradford Richmond Road, Bradford, BD7 1DP, United Kingdom ICGM, Univ Montpellier CNRS, ENSCM, Montpellier, France Export Date: 19 February 2022 CODEN: DTARA Correspondence Address: Deák, A.; Supramolecular Chemistry Research Group, Magyar Tudósok körútja 2, Hungary; email: deak.andrea@ttk.hu Funding details: European Cooperation in Science and Technology, COST Funding details: Vysoké Učení Technické v Brně, BUT Funding details: Central European Institute of Technology, CEITEC Funding text 1: This article is based upon work from COST Action CA18112,72,73 supported by COST (European Cooperation in Science and Technology).‡§ The authors are indebted to Dr Tamás Holczbauer, Dr Nóra May and Laura Nagyné Dr Bereczki for single crystal X-ray diffraction (Research Centre for Natural Sciences, Eötvös Loránd Research Network, Budapest, Hungary) and Mariano Casas Luna (Central European Institute of Technology, Brno University of Technology, Brno, Czech Republic) for the PXRD measurements. Funding text 2: This article is based upon work from COST Action CA18112,72,73supported by COST (European Cooperation in Science and Technology).The authors are indebted to Dr Tam?s Holczbauer, Dr N?ra May and Laura Nagyn? Dr Bereczki for single crystal X-ray diffraction (Research Centre for Natural Sciences, E?tv?s Lor?nd Research Network, Budapest, Hungary) and Mariano Casas Luna (Central European Institute of Technology, Brno University of Technology, Brno, Czech Republic) for the PXRD measurements. LA - English DB - MTMT ER - TY - JOUR AU - Gao, Qinghe AU - Sun, Zhenhua AU - Xia, Qinfei AU - Li, Ruonan AU - Wang, Wenlong AU - Ma, Siwei AU - Chai, Yixin AU - Wu, Manman AU - Hu, Wei AU - Ábrányi-Balogh, Péter AU - Keserű, György Miklós AU - Han, Xinya TI - Vinylation of alpha-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment JF - ORGANIC LETTERS J2 - ORG LETT VL - 23 PY - 2021 IS - 7 SP - 2664 EP - 2669 PG - 6 SN - 1523-7060 DO - 10.1021/acs.orglett.1c00571 UR - https://m2.mtmt.hu/api/publication/32404469 ID - 32404469 AB - A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon. LA - English DB - MTMT ER -