@article{MTMT:34778896, title = {Computational Studies on the Diastereospecific Lithium Variant of Oppenauer Oxidation of a Tofisopam Intermediate}, url = {https://m2.mtmt.hu/api/publication/34778896}, author = {Ábrányi-Balogh, Péter and Molnárné Samu, Erika and Pánczél, János K. and Benkő, Zoltán and Simig, Gyula and Volk, Balázs}, doi = {10.1021/acs.joc.3c02660}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, unique-id = {34778896}, issn = {0022-3263}, year = {2024}, eissn = {1520-6904}, orcid-numbers = {Benkő, Zoltán/0000-0001-6647-8320; Simig, Gyula/0000-0002-2569-6476; Volk, Balázs/0000-0002-2019-1874} } @article{MTMT:34445373, title = {Electrophilic MiniFrags Revealed Unprecedented Binding Sites for Covalent HDAC8 Inhibitors}, url = {https://m2.mtmt.hu/api/publication/34445373}, author = {Keeley, Aaron Brian and Kopranovic, Aleksandra and Di Lorenzo, Vincenzo and Ábrányi-Balogh, Péter and Jänsch, Niklas and Lai, Linh N. and Petri, László and Orgován, Zoltán and Pölöske, Daniel and Orlova, Anna and Németh, András György and Desczyk, Charlotte and Imre, Timea and Bajusz, Dávid and Moriggl, Richard and Meyer-Almes, Franz-Josef and Keserű, György Miklós}, doi = {10.1021/acs.jmedchem.3c01779}, journal-iso = {J MED CHEM}, journal = {JOURNAL OF MEDICINAL CHEMISTRY}, volume = {67}, unique-id = {34445373}, issn = {0022-2623}, abstract = {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}, year = {2024}, eissn = {1520-4804}, pages = {572-585}, orcid-numbers = {Di Lorenzo, Vincenzo/0000-0002-3140-3561; Bajusz, Dávid/0000-0003-4277-9481; Meyer-Almes, Franz-Josef/0000-0002-1001-3249} } @article{MTMT:34160949, title = {Covalent fragment approaches targeting non-cysteine residues}, url = {https://m2.mtmt.hu/api/publication/34160949}, author = {Csorba, Noémi and Ábrányi-Balogh, Péter and Keserű, György Miklós}, doi = {10.1016/j.tips.2023.08.014}, journal-iso = {TRENDS PHARMACOL SCI}, journal = {TRENDS IN PHARMACOLOGICAL SCIENCES}, volume = {44}, unique-id = {34160949}, issn = {0165-6147}, year = {2023}, eissn = {1873-3735}, pages = {802-816} } @article{MTMT:33647485, title = {Covalent fragment mapping of KRasG12C revealed novel chemotypes with in vivo potency}, url = {https://m2.mtmt.hu/api/publication/33647485}, author = {Orgován, Zoltán and Péczka, Nikolett and Petri, László and Ábrányi-Balogh, Péter and Randelovic, Ivan and Tóth, Szilárd and Szakács, Gergely and Nyíri, Kinga and Vértessy, Beáta (Grolmuszné) and Pálfy, Gyula and Vida, István and Perczel, András and Tóvári, József and Keserű, György Miklós}, doi = {10.1016/j.ejmech.2023.115212}, journal-iso = {EUR J MED CHEM}, journal = {EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY}, volume = {250}, unique-id = {33647485}, issn = {0223-5234}, abstract = {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.}, year = {2023}, eissn = {1768-3254}, orcid-numbers = {Randelovic, Ivan/0000-0003-0161-0022; Pálfy, Gyula/0000-0003-1590-5331; Perczel, András/0000-0003-1252-6416; Tóvári, József/0000-0002-5543-3204} } @article{MTMT:33729477, title = {Activation-Free Sulfonyl Fluoride Probes for Fragment Screening}, url = {https://m2.mtmt.hu/api/publication/33729477}, author = {Petri, László and Ábrányi-Balogh, Péter and Csorba, Noémi and Keeley, Aaron Brian and Simon, József and Randelovic, Ivan and Tóvári, József and Schlosser, Gitta (Vácziné) and Szabó, Dániel and Drahos, László and Keserű, György Miklós}, doi = {10.3390/molecules28073042}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {28}, unique-id = {33729477}, issn = {1420-3049}, abstract = {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.}, keywords = {fragment screening; chemical probe; Electrophilic warhead; Sulfonyl fluoride; Targeted covalent inhibitor; covalent fragment}, year = {2023}, eissn = {1420-3049}, orcid-numbers = {Randelovic, Ivan/0000-0003-0161-0022; Tóvári, József/0000-0002-5543-3204; Schlosser, Gitta (Vácziné)/0000-0002-7637-7133; Szabó, Dániel/0000-0003-3375-395X; Drahos, László/0000-0001-9589-6652} } @article{MTMT:34015800, title = {Synthesis and Application of Two-Photon Active Fluorescent Rhodol Dyes for Antibody Conjugation and In Vitro Cell Imaging}, url = {https://m2.mtmt.hu/api/publication/34015800}, author = {Szepesi Kovács, Dénes and Chiovini, Balázs and Müller, Dalma and Tóth, Estilla Zsófia and Fülöp, Anna and Ábrányi-Balogh, Péter and Wittner, Lucia and Várady, György and Farkas, Ödön and Turczel, Gábor and Katona, Gergely and Győrffy, Balázs and Keserű, György Miklós and Mucsi, Zoltán and Rózsa J., Balázs and Kovács, Ervin}, doi = {10.1021/acsomega.3c01796}, journal-iso = {ACS OMEGA}, journal = {ACS OMEGA}, volume = {8}, unique-id = {34015800}, issn = {2470-1343}, year = {2023}, eissn = {2470-1343}, pages = {22836-22843}, orcid-numbers = {Wittner, Lucia/0000-0001-6800-0953; Várady, György/0000-0003-2012-9680; Farkas, Ödön/0000-0002-4217-0150; Katona, Gergely/0000-0002-4173-0355; Győrffy, Balázs/0000-0002-5772-3766; Mucsi, Zoltán/0000-0003-3224-8847; Kovács, Ervin/0000-0002-3939-6925} } @article{MTMT:34205650, title = {Effective Synthesis, Development and Application of a Highly Fluorescent Cyanine Dye for Antibody Conjugation and Microscopy Imaging}, url = {https://m2.mtmt.hu/api/publication/34205650}, author = {Szepesi Kovács, Dénes and Kontra, Bence and Chiovini, Balázs and Müller, Dalma and Tóth, Estilla Zsófia and Ábrányi-Balogh, Péter and Wittner, Lucia and Várady, György and Turczel, Gábor and Farkas, Ödön and Owen, Michael Christopher and Katona, Gergely and Győrffy, Balázs and Keserű, György Miklós and Mucsi, Zoltán and Rózsa J., Balázs and Kovács, Ervin}, doi = {10.1039/D3OB01471A}, journal-iso = {ORG BIOMOL CHEM}, journal = {ORGANIC & BIOMOLECULAR CHEMISTRY}, volume = {21}, unique-id = {34205650}, issn = {1477-0520}, abstract = {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.}, keywords = {RECEPTOR; REAGENTS; FUTURE}, year = {2023}, eissn = {1477-0539}, pages = {8829-8836}, orcid-numbers = {Kontra, Bence/0000-0001-8293-3637; Wittner, Lucia/0000-0001-6800-0953; Várady, György/0000-0003-2012-9680; Farkas, Ödön/0000-0002-4217-0150; Katona, Gergely/0000-0002-4173-0355; Győrffy, Balázs/0000-0002-5772-3766; Mucsi, Zoltán/0000-0003-3224-8847; Kovács, Ervin/0000-0002-3939-6925} } @{MTMT:33650196, title = {Warheads for designing covalent inhibitors and chemical probes}, url = {https://m2.mtmt.hu/api/publication/33650196}, author = {Ábrányi-Balogh, Péter and Keserű, György Miklós}, booktitle = {Advances in Chemical Proteomics}, doi = {10.1016/B978-0-12-821433-6.00007-6}, unique-id = {33650196}, abstract = {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.}, keywords = {Covalent inhibitor; warhead; Amino acid labeling; Covalent probe; Electrophilic functionality}, year = {2022}, pages = {47-73} } @article{MTMT:33298396, title = {Next-Generation Heterocyclic Electrophiles as Small-Molecule Covalent MurA Inhibitors}, url = {https://m2.mtmt.hu/api/publication/33298396}, author = {Ábrányi-Balogh, Péter and Keeley, Aaron and Ferenczy, György and Petri, László and Imre, Timea and Grabrijan, Katarina and Hrast, Martina and Knez, Damijan and Ilaš, Janez and Gobec, Stanislav and Keserű, György Miklós}, doi = {10.3390/ph15121484}, journal-iso = {PHARMACEUTICALS-BASE}, journal = {PHARMACEUTICALS}, volume = {15}, unique-id = {33298396}, abstract = {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.}, year = {2022}, eissn = {1424-8247}, orcid-numbers = {Ferenczy, György/0000-0002-5771-4616; Hrast, Martina/0000-0003-0488-2445; Knez, Damijan/0000-0001-9917-1384; Ilaš, Janez/0000-0002-0124-0474; Gobec, Stanislav/0000-0002-9678-3083} } @article{MTMT:33050385, title = {A Study on the Direct Esterification of Monoalkylphosphates and Dialkylphosphates; The Conversion of the Latter Species to Trialkylphosphates by Alkylating Esterification}, url = {https://m2.mtmt.hu/api/publication/33050385}, author = {Ábrányi-Balogh, Péter and Harsági, Nikoletta and Drahos, László and Keglevich, György}, doi = {10.3390/molecules27154674}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {27}, unique-id = {33050385}, issn = {1420-3049}, abstract = {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.}, year = {2022}, eissn = {1420-3049}, orcid-numbers = {Drahos, László/0000-0001-9589-6652} } @article{MTMT:33126961, title = {Covalent inhibitors of bacterial peptidoglycan biosynthesis enzyme MurA with chloroacetamide warhead}, url = {https://m2.mtmt.hu/api/publication/33126961}, author = {Grabrijan, K. and Hrast, M. and Proj, M. and Dolšak, A. and Zdovc, I. and Imre, Timea and Petri, László and Ábrányi-Balogh, Péter and Keserű, György Miklós and Gobec, S.}, doi = {10.1016/j.ejmech.2022.114752}, journal-iso = {EUR J MED CHEM}, journal = {EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY}, volume = {243}, unique-id = {33126961}, issn = {0223-5234}, year = {2022}, eissn = {1768-3254} } @article{MTMT:32518471, title = {Microwave-assisted esterification of P-acids}, url = {https://m2.mtmt.hu/api/publication/32518471}, author = {Harsági, Nikoletta and Kiss, Nóra Zsuzsa and Ábrányi-Balogh, Péter and Keglevich, György}, doi = {10.1080/10426507.2021.1990925}, journal-iso = {PHOSPHOR SULFUR SIL REL ELEM}, journal = {PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS}, volume = {197}, unique-id = {32518471}, issn = {1042-6507}, abstract = {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.}, year = {2022}, eissn = {1563-5325}, pages = {529-531} } @article{MTMT:32672327, title = {Experimental and computational study of BF3-catalyzed transformations of ortho-(pivaloylaminomethyl)benzaldehydes: an unexpected difference from TFA catalysis}, url = {https://m2.mtmt.hu/api/publication/32672327}, author = {Koványiné Lax, Györgyi and Hargitai, Csilla Eszter and Ábrányi-Balogh, Péter and Nagy, Tamás and Tóth, Gábor and Garádi, Zsófia and Németh, Gábor and Pandur, Angéla and Horváth, Simon and Dancsó, András and Simig, Gyula and Volk, Balázs}, doi = {10.1039/D1OB02308J}, journal-iso = {ORG BIOMOL CHEM}, journal = {ORGANIC & BIOMOLECULAR CHEMISTRY}, volume = {20}, unique-id = {32672327}, issn = {1477-0520}, year = {2022}, eissn = {1477-0539}, pages = {1933-1944}, orcid-numbers = {Garádi, Zsófia/0000-0002-0152-2746; Németh, Gábor/0000-0003-3114-5125; Dancsó, András/0000-0001-8460-217X; Simig, Gyula/0000-0002-2569-6476; Volk, Balázs/0000-0002-2019-1874} } @article{MTMT:33543663, title = {Sejtosztódásgátló hatású vindolin- és flavonoidszármazékok előállítása}, url = {https://m2.mtmt.hu/api/publication/33543663}, author = {Mayer, Szabolcs and Nagy, Nóra and Keglevich, Péter and Ábrányi-Balogh, Péter and Hazai, László}, doi = {10.24100/MKF.2022.03-4.137}, journal-iso = {MAGY KÉM FOLY KÉM KÖZL}, journal = {MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-)}, volume = {128}, unique-id = {33543663}, issn = {1418-9933}, year = {2022}, eissn = {1418-8600}, pages = {137-142} } @article{MTMT:32832471, title = {A stepwise one-pot synthesis of aliphatic thiols and their derivatives from acrylamides and sulfur}, url = {https://m2.mtmt.hu/api/publication/32832471}, author = {Németh, András György and Szabó, Renáta and Németh, Krisztina and Keserű, György Miklós and Ábrányi-Balogh, Péter}, doi = {10.1039/D2OB00512C}, journal-iso = {ORG BIOMOL CHEM}, journal = {ORGANIC & BIOMOLECULAR CHEMISTRY}, volume = {20}, unique-id = {32832471}, issn = {1477-0520}, abstract = {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.}, year = {2022}, eissn = {1477-0539}, pages = {4361-4368} } @article{MTMT:32756662, title = {Electrophilic warheads in covalent drug discovery: an overview}, url = {https://m2.mtmt.hu/api/publication/32756662}, author = {Péczka, Nikolett and Orgován, Zoltán and Ábrányi-Balogh, Péter and Keserű, György Miklós}, doi = {10.1080/17460441.2022.2034783}, journal-iso = {EXPERT OPIN DRUG DIS}, journal = {EXPERT OPINION ON DRUG DISCOVERY}, volume = {17}, unique-id = {32756662}, issn = {1746-0441}, year = {2022}, eissn = {1746-045X}, pages = {413-422} } @article{MTMT:32649994, title = {A covalent strategy to target intrinsically disordered proteins: Discovery of novel tau aggregation inhibitors}, url = {https://m2.mtmt.hu/api/publication/32649994}, author = {Petri, László and Ábrányi-Balogh, Péter and Vagrys, Darius and Imre, Timea and Varró, Nikolett and Mándity, István and Rácz, Anita and Wittner, Lucia and Tóth, Kinga and Tóth, Estilla Zsófia and Juhász, Tünde and Davis, Ben and Keserű, György Miklós}, doi = {10.1016/j.ejmech.2022.114163}, journal-iso = {EUR J MED CHEM}, journal = {EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY}, volume = {231}, unique-id = {32649994}, issn = {0223-5234}, year = {2022}, eissn = {1768-3254}, orcid-numbers = {Vagrys, Darius/0000-0002-8988-9787; Varró, Nikolett/0000-0003-4161-9021; Mándity, István/0000-0003-2865-6143; Wittner, Lucia/0000-0001-6800-0953; Tóth, Kinga/0000-0002-8751-8499} } @article{MTMT:32557263, title = {A Mechanistic Study on the Formation of Dronic Acids}, url = {https://m2.mtmt.hu/api/publication/32557263}, author = {Ábrányi-Balogh, Péter and Greiner, István and Keglevich, György}, doi = {10.3390/molecules26247587}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {26}, unique-id = {32557263}, issn = {1420-3049}, abstract = {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.}, year = {2021}, eissn = {1420-3049}, orcid-numbers = {Greiner, István/0000-0002-5336-2828} } @article{MTMT:32234667, title = {Mechanochemical synthesis of mononuclear gold( i ) halide complexes of diphosphine ligands with tuneable luminescent properties}, url = {https://m2.mtmt.hu/api/publication/32234667}, author = {Deák, Andrea Beáta and Jobbágy, Csaba and Demeter, Attila and Čelko, Ladislav and Cihlář, Jaroslav and Szabó, Pál Tamás and Ábrányi-Balogh, Péter and Crawford, Deborah E. and Virieux, David and Colacino, Evelina}, doi = {10.1039/D1DT01751A}, journal-iso = {J CHEM SOC DALTON TRANS}, journal = {JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS}, volume = {50}, unique-id = {32234667}, issn = {1472-7773}, year = {2021}, pages = {13337-13344}, orcid-numbers = {Szabó, Pál Tamás/0000-0003-2260-4641; Virieux, David/0000-0002-6495-9478; Colacino, Evelina/0000-0002-1179-4913} } @article{MTMT:32404469, title = {Vinylation of alpha-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment}, url = {https://m2.mtmt.hu/api/publication/32404469}, author = {Gao, Qinghe and Sun, Zhenhua and Xia, Qinfei and Li, Ruonan and Wang, Wenlong and Ma, Siwei and Chai, Yixin and Wu, Manman and Hu, Wei and Ábrányi-Balogh, Péter and Keserű, György Miklós and Han, Xinya}, doi = {10.1021/acs.orglett.1c00571}, journal-iso = {ORG LETT}, journal = {ORGANIC LETTERS}, volume = {23}, unique-id = {32404469}, issn = {1523-7060}, abstract = {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.}, year = {2021}, eissn = {1523-7052}, pages = {2664-2669}, orcid-numbers = {Gao, Qinghe/0000-0002-6207-8933} }