@article{MTMT:30345384, title = {Synthesis, in Vitro Biological Evaluation, and Oxidative Transformation of New Flavonol Derivatives. The Possible Role of the Phenyl-N,N-Dimethylamino Group.}, url = {https://m2.mtmt.hu/api/publication/30345384}, author = {Szabados-Fürjesi, Péter and Pajtás, Dávid and Barta, Aliz and Csépányi, Evelin and Kiss, Attila and Tósaki, Árpád and Bak, István}, doi = {10.3390/molecules23123161}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {23}, unique-id = {30345384}, issn = {1420-3049}, abstract = {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.}, keywords = {CYTOTOXICITY; ANTIOXIDANT; flavonoid; Flavonol; Oxidative metabolism}, year = {2018}, eissn = {1420-3049}, orcid-numbers = {Kiss, Attila/0000-0003-3601-5143} } @article{MTMT:26755248, title = {Synthesis of 6,7-Dibromoflavone and Its Regioselective Diversification via Suzuki-Miyaura Reactions}, url = {https://m2.mtmt.hu/api/publication/26755248}, author = {Jordán, Sándor and Pajtás, Dávid and Patonay, Tamás and Langer, Peter and Kónya, Krisztina}, doi = {10.1055/s-0036-1588376}, journal-iso = {SYNTHESIS-STUTTGART}, journal = {SYNTHESIS-STUTTGART}, volume = {49}, unique-id = {26755248}, issn = {0039-7881}, abstract = {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.}, keywords = {PALLADIUM; CATALYSIS; regioselectivity; flavones; Suzuki-Miyaura reaction}, year = {2017}, eissn = {1437-210X}, pages = {1983-1992} } @article{MTMT:3245969, title = {Optimization of the Synthesis of Flavone–Amino Acid and Flavone–Dipeptide Hybrids via Buchwald–Hartwig Reaction}, url = {https://m2.mtmt.hu/api/publication/3245969}, author = {Pajtás, Dávid and Kónya, Krisztina and Kiss, Attila and Džubák, Petr and Pethő, Zoltán Dénes and Varga, Zoltán and Panyi, György and Patonay, Tamás}, doi = {10.1021/acs.joc.7b00124}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {82}, unique-id = {3245969}, issn = {0022-3263}, abstract = {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.}, year = {2017}, eissn = {1520-6904}, pages = {4578-4587}, orcid-numbers = {Kiss, Attila/0000-0003-3601-5143; Panyi, György/0000-0001-6227-3301} } @article{MTMT:3035601, title = {Regioselective Suzuki–Miyaura Reactions of the Bis(triflate) of 6,7-Dihydroxy-2,2-dimethylchroman-4-one}, url = {https://m2.mtmt.hu/api/publication/3035601}, author = {Pajtás, Dávid and Károly, Dihen and Kónya, Krisztina and Peter, Langer}, doi = {10.1055/s-0035-1561265}, journal-iso = {SYNLETT}, journal = {SYNLETT}, volume = {27}, unique-id = {3035601}, issn = {0936-5214}, abstract = {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.}, keywords = {PALLADIUM; CATALYSIS; HETEROCYCLES; regioselectivity; Suzuki-Miyaura reaction}, year = {2016}, eissn = {1437-2096}, pages = {1073-1076} } @mastersthesis{MTMT:3015716, title = {Aminoflavon származékok, valamint flavon-aminosav hibridek előállítása Buchwald-Hartwig reakcióval}, url = {https://m2.mtmt.hu/api/publication/3015716}, author = {Pajtás, Dávid}, unique-id = {3015716}, year = {2016} } @article{MTMT:2988364, title = {Synthesis of 8-Bromoflavone and Its Buchwald–Hartwig Reaction with Amines}, url = {https://m2.mtmt.hu/api/publication/2988364}, author = {Pajtás, Dávid and Patonay, Tamás and Kónya, Krisztina}, doi = {10.1055/s-0035-1560325}, journal-iso = {SYNTHESIS-STUTTGART}, journal = {SYNTHESIS-STUTTGART}, volume = {48}, unique-id = {2988364}, issn = {0039-7881}, abstract = {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.}, keywords = {PALLADIUM; CATALYSIS; flavones; Buchwald-Hartwig; Buchwald–Hartwig reaction; Fries rearrangement}, year = {2016}, eissn = {1437-210X}, pages = {97-102} } @article{MTMT:3035594, title = {Site-Selective Suzuki–Miyaura Reaction of 6,8-Dibromoflavone}, url = {https://m2.mtmt.hu/api/publication/3035594}, author = {Pajtás, Dávid and Károly, Dihen and Patonay, Tamás and Kónya, Krisztina and Alexander, Villinger and Peter, Langer}, doi = {10.1055/s-0035-1560633}, journal-iso = {SYNLETT}, journal = {SYNLETT}, volume = {26}, unique-id = {3035594}, issn = {0936-5214}, abstract = {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.}, keywords = {PALLADIUM; CATALYSIS; regioselectivity; flavones; Suzuki-Miyaura reaction}, year = {2015}, eissn = {1437-2096}, pages = {2601-2605} } @article{MTMT:2873077, title = {Buchwald–Hartwig Reactions of Monohaloflavones}, url = {https://m2.mtmt.hu/api/publication/2873077}, author = {Kónya, Krisztina and Pajtás, Dávid and Kiss, Attila and Patonay, Tamás}, doi = {10.1002/ejoc.201403108}, journal-iso = {EUR J ORG CHEM}, journal = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}, volume = {2015}, unique-id = {2873077}, issn = {1434-193X}, abstract = {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.}, keywords = {PALLADIUM; amino acids; amination; cross-coupling; homogeneous catalysis; Oxygen heterocycles}, year = {2015}, eissn = {1099-0690}, pages = {828-839}, orcid-numbers = {Kiss, Attila/0000-0003-3601-5143} }