TY - JOUR AU - Szabados-Fürjesi, Péter AU - Pajtás, Dávid AU - Barta, Aliz AU - Csépányi, Evelin AU - Kiss, Attila AU - Tósaki, Árpád AU - Bak, István TI - Synthesis, in Vitro Biological Evaluation, and Oxidative Transformation of New Flavonol Derivatives. The Possible Role of the Phenyl-N,N-Dimethylamino Group. TS - The Possible Role of the Phenyl-N,N-Dimethylamino Group. JF - MOLECULES J2 - MOLECULES VL - 23 PY - 2018 IS - 12 PG - 15 SN - 1420-3049 DO - 10.3390/molecules23123161 UR - https://m2.mtmt.hu/api/publication/30345384 ID - 30345384 AB - Six new flavonols (6a⁻f) were synthesized with Claisen⁻Schmidt and Suzuki reactions and they were fully characterized by spectroscopic methods. In order to evaluate their antioxidant activities, their oxygen radical absorption capacity and ferric reducing antioxidant power were measured, along with their free radical scavenging activity against 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and 2,2-diphenyl-1-picrylhydrazylradicals. In addition, their cytotoxicity on H9c2 cardiomyoblast cells was also assessed by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Compounds bearing the phenyl-N,N-dimethylamino group (6a, 6c, and 6e) exhibited promising antioxidant potency and did not have any cytotoxic effect. After a consideration of these data, the oxidative transformation of the 6c compound was investigated in vitro with a chemical Fenton reaction and the identification of the formed oxidation products was performed by mass spectrometry. Two potential metabolites were detected. Based on these results, compound 6c can be a model compound for future developments. Overall, this work has proved the involvement of the phenyl-N,N-dimethylamino group in the antioxidant activity of flavonols. LA - English DB - MTMT ER - TY - JOUR AU - Jordán, Sándor AU - Pajtás, Dávid AU - Patonay, Tamás AU - Langer, Peter AU - Kónya, Krisztina TI - Synthesis of 6,7-Dibromoflavone and Its Regioselective Diversification via Suzuki-Miyaura Reactions JF - SYNTHESIS-STUTTGART J2 - SYNTHESIS-STUTTGART VL - 49 PY - 2017 IS - 9 SP - 1983 EP - 1992 PG - 10 SN - 0039-7881 DO - 10.1055/s-0036-1588376 UR - https://m2.mtmt.hu/api/publication/26755248 ID - 26755248 AB - The first synthesis pathway to 6,7-dibromoflavone and its transformations to 7-aryl-6-bromo- and 6,7-diarylflavones by Suzuki-Miyaura reactions are presented. Due to the different electronic effects of bromo substituents, the first attack proceeded with good site selectivity at position 7. LA - English DB - MTMT ER - TY - JOUR AU - Pajtás, Dávid AU - Kónya, Krisztina AU - Kiss, Attila AU - Džubák, Petr AU - Pethő, Zoltán Dénes AU - Varga, Zoltán AU - Panyi, György AU - Patonay, Tamás TI - Optimization of the Synthesis of Flavone–Amino Acid and Flavone–Dipeptide Hybrids via Buchwald–Hartwig Reaction JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 82 PY - 2017 IS - 9 SP - 4578 EP - 4587 PG - 10 SN - 0022-3263 DO - 10.1021/acs.joc.7b00124 UR - https://m2.mtmt.hu/api/publication/3245969 ID - 3245969 AB - The article describes the development of Buchwald–Hartwig amination of different bromoflavones with amino acid and peptide derivatives as nitrogen source giving unique structures. The previously observed racemization, which occurred during the synthesis of flavone-amino acid hybrids, was successfully prevented in most cases. The biological assays of these novel structures showed cytotoxic effects on different cancer cell lines. LA - English DB - MTMT ER - TY - JOUR AU - Pajtás, Dávid AU - Károly, Dihen AU - Kónya, Krisztina AU - Peter, Langer TI - Regioselective Suzuki–Miyaura Reactions of the Bis(triflate) of 6,7-Dihydroxy-2,2-dimethylchroman-4-one JF - SYNLETT J2 - SYNLETT VL - 27 PY - 2016 IS - 7 SP - 1073 EP - 1076 PG - 4 SN - 0936-5214 DO - 10.1055/s-0035-1561265 UR - https://m2.mtmt.hu/api/publication/3035601 ID - 3035601 AB - 6,7-Diarylchromanone derivatives were prepared by Suzuki–Miyaura reactions of the bis(triflate) of 6,7-dihydroxy-2,2-dimethylchroman-4-one. Due to electronic factors the first attack proceeded with very good site selectivity at position 7. LA - English DB - MTMT ER - TY - THES AU - Pajtás, Dávid TI - Aminoflavon származékok, valamint flavon-aminosav hibridek előállítása Buchwald-Hartwig reakcióval PY - 2016 UR - https://m2.mtmt.hu/api/publication/3015716 ID - 3015716 N1 - Tudományág: kémiai tudományok Témavezető: Patonay Tamás (1951-2015) Beadás éve: 2015 A védés időpontja: 2015-12-01 11:00 A fokozat odaítélésének dátuma: 2016-01-27 Debreceni Egyetem, Kémia Doktori Iskola Debrecen, Magyarország LA - Hungarian DB - MTMT ER - TY - JOUR AU - Pajtás, Dávid AU - Patonay, Tamás AU - Kónya, Krisztina TI - Synthesis of 8-Bromoflavone and Its Buchwald–Hartwig Reaction with Amines JF - SYNTHESIS-STUTTGART J2 - SYNTHESIS-STUTTGART VL - 48 PY - 2016 IS - 1 SP - 97 EP - 102 PG - 6 SN - 0039-7881 DO - 10.1055/s-0035-1560325 UR - https://m2.mtmt.hu/api/publication/2988364 ID - 2988364 AB - Simple and convenient synthesis of 8-bromoflavone was achieved, starting from 2-bromophenol through 3′-bromo-2′-hydroxyacetophenone whose preparation was managed to be solved by optimized Fries rearrangement. The Buchwald–Hartwig reaction of 8-bromoflavone with different type of primary and secondary amines was carried out. LA - English DB - MTMT ER - TY - JOUR AU - Pajtás, Dávid AU - Károly, Dihen AU - Patonay, Tamás AU - Kónya, Krisztina AU - Alexander, Villinger AU - Peter, Langer TI - Site-Selective Suzuki–Miyaura Reaction of 6,8-Dibromoflavone JF - SYNLETT J2 - SYNLETT VL - 26 PY - 2015 IS - 18 SP - 2601 EP - 2605 PG - 5 SN - 0936-5214 DO - 10.1055/s-0035-1560633 UR - https://m2.mtmt.hu/api/publication/3035594 ID - 3035594 AB - 8-Aryl- and 6,8-diarylflavones were prepared by Suzuki–Miyaura reactions of 6,8-dibromoflavone. In spite of the greater steric hindrance, the first attack proceeded with good site selectivity at position 8. LA - English DB - MTMT ER - TY - JOUR AU - Kónya, Krisztina AU - Pajtás, Dávid AU - Kiss, Attila AU - Patonay, Tamás TI - Buchwald–Hartwig Reactions of Monohaloflavones JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2015 PY - 2015 IS - 4 SP - 828 EP - 839 PG - 12 SN - 1434-193X DO - 10.1002/ejoc.201403108 UR - https://m2.mtmt.hu/api/publication/2873077 ID - 2873077 AB - The article describes the amination of different monobromoor monochloroflavones with primary and secondary alkylamines and aniline derivatives by Buchwald–Hartwig reaction. The influence of the phosphine ligands used is described. The use of amino acid derivatives as a nitrogen source is also demonstrated. This latter reaction allows the synthesis of unique flavone–amino-acid conjugates. LA - English DB - MTMT ER -