@article{MTMT:33913826, title = {Nickel-catalyzed N-arylation of optically pure amino acid esters with activated (hetero)aryl electrophiles}, url = {https://m2.mtmt.hu/api/publication/33913826}, author = {Lundrigan, Travis and Tassone, Joseph P. and Stradiotto, Mark}, doi = {10.1139/cjc-2022-0290}, journal-iso = {CAN J CHEM}, journal = {CANADIAN JOURNAL OF CHEMISTRY}, volume = {101}, unique-id = {33913826}, issn = {0008-4042}, abstract = {An efficient method for the C-N cross-coupling of (hetero)aryl (pseudo)halides with optically pure alpha-amino acid esters em-ploying a commercially available nickel catalyst and weak inorganic base was developed. This is the first example of Ni-catalyzed N-arylation of amino acid esters without the use of electrochemistry, which was shown to effectively couple a variety of amino acid tert-butyl esters with (hetero)aryl chlorides, bromides, and tosylates in high yields and excellent enantioreten-tion. Base-mediated racemization was revealed during control experiments, but increasing the steric bulk of the amino acid ester group limited the amount of racemization of the product.}, keywords = {NICKEL; amination; cross-coupling; amino acid esters}, year = {2023}, eissn = {1480-3291}, pages = {275-283}, orcid-numbers = {Stradiotto, Mark/0000-0002-6913-5160} } @article{MTMT:33856060, title = {Synthesis and In Vitro Anticancer Evaluation of Chrysin Containing Hybrids and Other Chrysin Derivatives}, url = {https://m2.mtmt.hu/api/publication/33856060}, author = {Mayer, Szabolcs and Herr, Dominika Mária and Nagy, Nóra and Donkó-Tóth, Viktória and Keglevich, Péter and Weber, Márton and Dékány, Miklós and Hazai, László}, doi = {10.3311/PPch.21919}, journal-iso = {PERIOD POLYTECH CHEM ENG}, journal = {PERIODICA POLYTECHNICA-CHEMICAL ENGINEERING}, volume = {67}, unique-id = {33856060}, issn = {0324-5853}, abstract = {Chrysin, a well-known naturally occurring flavonoid having several biological effects including antiproliferative activity, was coupled with different pharmacophore structures. Coupling was carried out with spacers of different lengths and types. Structures selected for hybrid formation were amines, cyclic amino acid esters, and (hetero)aromatic compounds. In addition, vindoline, which is a Vinca alkaloid containing an indole skeleton, was also used. The alkylation of amines in the presence of carbonate base resulted in an interesting carbamate side product formation beside the expected amine. We also present the detailed structure elucidation of the carbamates. The in vitro anticancer activities of the synthesized derivatives were examined against 60 human tumor cell lines in National Cancer Institute (NCI, USA).}, year = {2023}, eissn = {1587-3765}, pages = {316-336}, orcid-numbers = {Herr, Dominika Mária/0009-0003-7538-2752} } @article{MTMT:33913827, title = {Synthesis of Mono- and Polyazole Hybrids Based on Polyfluoroflavones}, url = {https://m2.mtmt.hu/api/publication/33913827}, author = {Panova, Mariya A. and Shcherbakov, Konstantin V. and Zhilina, Ekaterina F. and Burgart, Yanina V. and Saloutin, Victor I.}, doi = {10.3390/molecules28020869}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {28}, unique-id = {33913827}, issn = {1420-3049}, abstract = {The possibility of functionalization of 2-(polyfluorophenyl)-4H-chromen-4-ones, with them having different numbers of fluorine atoms, with 1,2,4-triazole or imidazole under conditions of base-promoted nucleophilic aromatic substitution has been shown. A high selectivity of mono-substitution was found with the use of an azole (1.5 equiv.)/NaOBut(1.5 equiv.)/MeCN system. The structural features of fluorinated mono(azolyl)-substituted flavones in crystals were established using XRD analysis. The ability of penta- and tetrafluoroflavones to form persubstituted products with triazole under azole (6 equiv.)/NaOBut(6 equiv.)/DMF conditions was found in contrast to similar transformations with imidazole. On the basis of mono(azolyl)-containing polyfluoroflavones in reactions with triazole and pyrazole, polynuclear hybrid compounds containing various azole fragments were obtained. For poly(pyrazolyl)-substituted flavones, green emission in the solid state under UV-irradiation was found, and for some derivatives, weak fungistatic activity was found.}, keywords = {PHOTOLUMINESCENCE; regioselectivity; IMIDAZOLE; NUCLEOPHILIC AROMATIC SUBSTITUTION; 2; 4-triazole; 1H-1; polyfluoroflavones; azolyl-substituted flavones}, year = {2023}, eissn = {1420-3049} } @article{MTMT:33841551, title = {Stereoselective Synthesis of Flavonoids: A Brief Overview}, url = {https://m2.mtmt.hu/api/publication/33841551}, author = {Pereira, Ana Margarida and Cidade, Honorina and Tiritan, Maria Elizabeth}, doi = {10.3390/molecules28010426}, journal-iso = {MOLECULES}, journal = {MOLECULES}, volume = {28}, unique-id = {33841551}, issn = {1420-3049}, abstract = {Stereoselective synthesis has been emerging as a resourceful tool because it enables the obtaining of compounds with biological interest and high enantiomeric purity. Flavonoids are natural products with several biological activities. Owing to their biological potential and aiming to achieve enantiomerically pure forms, several methodologies of stereoselective synthesis have been implemented. Those approaches encompass stereoselective chalcone epoxidation, Sharpless asymmetric dihydroxylation, Mitsunobu reaction, and the cycloaddition of 1,4-benzoquinone. Chiral auxiliaries, organo-, organometallic, and biocatalysis, as well as the chiral pool approach were also employed with the goal of obtaining chiral bioactive flavonoids with a high enantiomeric ratio. Additionally, the employment of the Diels-Alder reaction based on the stereodivergent reaction on a racemic mixture strategy or using catalyst complexes to synthesise pure enantiomers of flavonoids was reported. Furthermore, biomimetic pathways displayed another approach as illustrated by the asymmetric coupling of 2-hydroxychalcones driven by visible light. Recently, an asymmetric transfer hydrogen-dynamic kinetic resolution was also applied to synthesise (R,R)-cis-alcohols which, in turn, would be used as building blocks for the stereoselective synthesis of flavonoids.}, keywords = {ENANTIOMERS; Flavonoids; enantioselective synthesis; chiral}, year = {2023}, eissn = {1420-3049}, orcid-numbers = {Pereira, Ana Margarida/0000-0002-5468-0932; Tiritan, Maria Elizabeth/0000-0003-3320-730X} } @article{MTMT:33340240, title = {Flavonoids with antioxidant and tyrosinase inhibitory activity from corn silk (Stigma maydis)}, url = {https://m2.mtmt.hu/api/publication/33340240}, author = {Wang, Jia-yi and Zhou, Wei-yu and Huang, Xiao-xiao and Song, Shao-jiang}, doi = {10.1080/14786419.2022.2089986}, journal-iso = {NAT PROD RES}, journal = {NATURAL PRODUCT RESEARCH}, volume = {37}, unique-id = {33340240}, issn = {1478-6419}, abstract = {Corn silk (Stigma maydis), being the styles and stigmas of maize, is a famous traditional medicine and functional tea in China. Research into the chemical composition of corn silk led to the identification of an unreported flavone (1, silkone A), accompanying with three known flavonoids (2-4). And their structures were elucidated through comprehensive spectroscopic analysis. Each obtained compound was evaluated for antioxidant capacity by DPPH, ABTS and FRAP assays. As a result, all tested compounds exhibited stronger radicals scavenging activities than Trolox in ABTS radical assay and displayed relatively weak antioxidant capacity in the other two experiments. Tyrosinase inhibitory activities of compounds 1-4 were also investigated, and compounds 3 and 4 demonstrated moderate inhibitory activities to tyrosinase with IC50 values of 0.49 and 0.21 mM, respectively, which was further investigated through molecular docking calculation. These results may contribute to the development of novel antioxidants and tyrosinase inhibitors from corn silk.}, keywords = {antioxidant activity; flavonoid; Corn silk; Tyrosinase inhibitory activity}, year = {2023}, eissn = {1478-6427}, pages = {835-839} } @article{MTMT:33340241, title = {Eucalyptol, an All-Purpose Product}, url = {https://m2.mtmt.hu/api/publication/33340241}, author = {Campos, Joana F. and Berteina-Raboin, Sabine}, doi = {10.3390/catal12010048}, journal-iso = {CATALYSTS}, journal = {CATALYSTS}, volume = {12}, unique-id = {33340241}, abstract = {Eucalyptus plants have attracted the attention of researchers and environmentalists worldwide because they are a rapidly growing source of wood and a source of oil used for multiple purposes. The main and the most important oil component is 1,8-cineole (eucalyptol: 60-85%). This review summarizes the literature reported to date involving the use of 1,8-cineole for the treatment of disorders. Additionally, we describe our efforts in the use of eucalyptol as a solvent for the synthesis of O,S,N-heterocycles. Solvents used in chemistry are a fundamental element of the environmental performance of processes in corporate and academic laboratories. Their influence on costs, safety and health cannot be neglected. Green solvents such as bio-based systems hold considerable additional promise to reduce the environmental impact of organic chemistry. The first section outlines the process leading to our discovery of an unprecedented solvent and its validation in the first coupling reactions. This section continues with the description of its properties and characteristics and its reuse as reported in the various studies conducted. The second section highlights the use of eucalyptol in a series of coupling reactions (i.e., Suzuki-Miyaura, Sonogashira-Hagihara, Buchwald-Hartwig, Migita-Kosugi-Stille, Hiyama and cyanation) that form O,S,N-heterocycles. We describe the optimization process applied to reach the ideal conditions. We also show that eucalyptol can be a good alternative to build heterocycles that contain oxygen, sulfur and nitrogen. These studies allowed us to demonstrate the viability and potential that bio solvents can have in synthesis laboratories.}, keywords = {Biology; green synthesis; 1; eucalyptol; Heterocyclic chemistry; 8-cineole}, year = {2022}, eissn = {2073-4344}, orcid-numbers = {Berteina-Raboin, Sabine/0000-0002-4577-4988} } @article{MTMT:33340239, title = {Synthesis of functionalized flavones from 3-halo-2-(methylthio)-4H-chromen-4-ones}, url = {https://m2.mtmt.hu/api/publication/33340239}, author = {Elagamy, Amr and Elghoneimy, Laila K. and Arafa, Reem K. and Pratap, Ramendra}, doi = {10.1016/j.tetlet.2022.153882}, journal-iso = {TETRAHEDRON LETT}, journal = {TETRAHEDRON LETTERS}, volume = {100}, unique-id = {33340239}, issn = {0040-4039}, abstract = {A simple and efficient method for the synthesis of flavones was achieved by selective sulfide LiebeskindSrogl cross-coupling reaction of 2-(methylthio)-4H-chromen-4-ones and 3-halo-2-(methylthio)-4H-chromen-4-ones with arylboronic acids. This method is the first example of employing Liebeskind-Srogl coupling for the synthesis of flavones. Various aryl groups can be directly installed to the chromone ring. The structure of all the synthesized compounds were assigned by spectroscopic analysis. (C) 2022 Elsevier Ltd. All rights reserved.}, keywords = {cross-coupling; flavones; 4H-CHROMEN-4-ONES; GSK-3 beta inhibitor}, year = {2022}, eissn = {1873-3581}, orcid-numbers = {Pratap, Ramendra/0000-0003-1846-1561} } @article{MTMT:33897419, title = {Molecular Docking Studies and Application of 6-(1-Arylmethanamino)-2-Phenyl-4H-Chromen-4-Ones as Potent Antibacterial Agents}, url = {https://m2.mtmt.hu/api/publication/33897419}, author = {Thorat, Nitin M. M. and Khodade, Vinnayak S. S. and Ingale, Ajit P. P. and Lokwani, Deepak K. K. and Sarkate, Aniket P. P. and Thopate, Shankar R. R.}, doi = {10.1080/10406638.2022.2150238}, journal-iso = {POLYCYCL AROMAT COMP}, journal = {POLYCYCLIC AROMATIC COMPOUNDS}, unique-id = {33897419}, issn = {1040-6638}, abstract = {The present article depicts the synthesis of the series of 6-(1-arylmethanamino)-2-phenyl-4H-chromen-4-ones and their antibacterial activity against the S. aureus. 6-(1-arylmethanamino)-2-phenyl-4H-chromen-4-ones (1a-1n) were obtained via reductive amination reaction of 6-aminoflavone with various commercially available aldehydes. Synthesized compounds and 6-aminoflavone (1) were assessed for their antimicrobial activities against the S. aureus. 6-aminoflavone (1) was found to have an MIC of 2 mu g/mL. The compounds with side chains 4-fluorobenzyl (1a), 4-chlorobenzyl (1b), 4-nitrobenzyl (1e), 4-methoxybenzyl (1g) and (quinolin-2-yl)methyl (1n) were found to have an MIC of 2 mu g/mL. We have demonstrated that 6-(1-arylmethanamino)-2-phenyl-4H-chromen-4-ones are easily accessible via reductive amination reaction. These compounds are found to have antibacterial effect against S. aureus.}, keywords = {REDUCTIVE AMINATION; Antibacterial agent; Molecular docking; 6-aminoflavone}, year = {2022}, eissn = {1563-5333} } @article{MTMT:32442026, title = {Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System}, url = {https://m2.mtmt.hu/api/publication/32442026}, author = {Ichitsuka, Tomohiro and Komatsuzaki, Shingo and Masuda, Koichiro and Koumura, Nagatoshi and Sato, Kazuhiko and Kobayashi, Shu}, doi = {10.1002/chem.202101439}, journal-iso = {CHEM-EUR J}, journal = {CHEMISTRY-A EUROPEAN JOURNAL}, volume = {27}, unique-id = {32442026}, issn = {0947-6539}, abstract = {The N-arylation of chiral amino acid esters with minimal racemization is a challenging transformation because of the sensitivity of the alpha-stereocenter. A versatile synthetic method was developed to prepare N-arylated amino acid esters using cyclohexanones as aryl sources under continuous-flow conditions. The designed flow system, which consists of a coil reactor and a packed-bed reactor containing a Pd(OH)(2)/C catalyst, efficiently afforded the desired N-arylated amino acids without significant racemization, accompanied by only small amounts of easily removable co-products (i. e., H2O and alkanes). The efficiency and robustness of this method allowed for the continuous synthesis of the desired product in very high yield and enantiopurity with high space-time yield (74.1 g L-1 h(-1)) and turnover frequency (5.9 h(-1)) for at least 3 days.}, keywords = {HETEROGENEOUS CATALYSIS; amino acids; Cyclohexanones; N-ARYLATION; Continuous-flow synthesis}, year = {2021}, eissn = {1521-3765}, pages = {10844-10848}, orcid-numbers = {Ichitsuka, Tomohiro/0000-0003-1099-6457; Sato, Kazuhiko/0000-0002-4929-4973} } @article{MTMT:33340242, title = {Chiral Flavonoids as Antitumor Agents}, url = {https://m2.mtmt.hu/api/publication/33340242}, author = {Pinto, Claudia and Cidade, Honorina and Pinto, Madalena and Tiritan, Maria Elizabeth}, doi = {10.3390/ph14121267}, journal-iso = {PHARMACEUTICALS-BASE}, journal = {PHARMACEUTICALS}, volume = {14}, unique-id = {33340242}, abstract = {Flavonoids are a group of natural products with a great structural diversity, widely distributed in plant kingdom. They play an important role in plant growth, development and defense against aggressors. Flavonoids show a huge variety of biological activities such as antioxidant, anti-inflammatory, anti-mutagenic, antimicrobial and antitumor, being able to modulate a large diversity of cellular enzymatic activities. Among natural flavonoids, some classes comprise chiral molecules including flavanones, flavan-3-ols, isoflavanones, and rotenoids, which have one or more stereogenic centers. Interestingly, in some cases, individual compounds of enantiomeric pairs have shown different antitumor activity. In nature, these compounds are mainly biosynthesized as pure enantiomers. Nevertheless, they are often isolated as racemates, being necessary to carry out their chiral separation to perform enantioselectivity studies. Synthetic chiral flavonoids with promising antitumor activity have also been obtained using diverse synthetic approaches. In fact, several new chiral bioactive flavonoids have been synthesized by enantioselective synthesis. Particularly, flavopiridol was the first cyclin-dependent kinase (CDK) inhibitor which entered clinical trials. The chiral pool approaches using amino acid as chiral building blocks have also been reported to achieve small libraries of chrysin derivatives with more potent in vitro growth inhibitory effect than chrysin, reinforcing the importance of the introduction of chiral moieties to improve antitumor activity. In this work, a literature review of natural and synthetic chiral flavonoids with antitumor activity is reported for the first time.}, keywords = {ENANTIOMERS; Flavonoids; enantioselective synthesis; chiral; antitumor}, year = {2021}, eissn = {1424-8247}, orcid-numbers = {Pinto, Claudia/0000-0002-7292-1517; Pinto, Madalena/0000-0002-4676-1409; Tiritan, Maria Elizabeth/0000-0003-3320-730X} } @article{MTMT:31067372, title = {Mechanochemical Synthesis, in vitro Evaluation and Molecular Docking Studies of 4-Amino-2-arylamino-5-(benzofuran-2-oyl)thiazoles as Antidiabetic Agents}, url = {https://m2.mtmt.hu/api/publication/31067372}, author = {Akhila, Vijayan R. and Priya, Maheswari R. and Sherin, Daisy R. and Krishnapriya, Girija K. and Keerthi, Sreerekha V. and Manojkumar, Thanathu K. and Rajasekharan, Kallikat N.}, doi = {10.2174/1570178615666180815124425}, journal-iso = {LETT ORG CHEM}, journal = {LETTERS IN ORGANIC CHEMISTRY}, volume = {16}, unique-id = {31067372}, issn = {1570-1786}, abstract = {The synthesis of 4-amino-2-arylamino-5-(benzofuran-2-oyl)thiazoles 4a-h, as example of 2,4-diaminothiazole-benzofuran hybrids and an evaluation of their antidiabetic activity, by in vitro and computational methods, are reported. The synthesis of these diaminothiazoles was achieved mechano chemically by a rapid solvent-less method. Their antidiabetic activity was assessed by alpha-glucosidase and alpha-amylase inhibition assays. The, IC50 value for alpha-glucosidase inhibition by 4-amino-5-(benzofuran-2-oyl)-2-(4-methoxyphenylamino)thiazole (4d) was found to be 20.04 mu M and the IC50 value for alpha-amylase inhibition, 195.03 mu M whereas the corresponding values for reference acarbose were 53.38 mu M and 502.03 mu M, respectively. Molecular docking studies at the active sites of alpha-glucosidase and alpha-amylase showed that among the diaminothiazoles 4a-h now studied, 4-amino-5-(benzofuran-2-oyl)-2-(4-methoxyphenylamino)thiazole (4d) has the highest D-scores of -8.63 and -8.08 for alpha-glucosidase and for alpha-amylase, with binding energies -47.76 and -19.73 kcal/mol, respectively.}, keywords = {ALKALOIDS; ALPHA-AMYLASE; Molecular docking; alpha-glucosidase; Mechanochemical; 2,4-diaminothiazoles}, year = {2019}, eissn = {1875-6255}, pages = {560-568} } @article{MTMT:31067370, title = {Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles}, url = {https://m2.mtmt.hu/api/publication/31067370}, author = {Campos, Joana E. and Berteina-Raboin, Sabine}, doi = {10.3390/catal9100840}, journal-iso = {CATALYSTS}, journal = {CATALYSTS}, volume = {9}, unique-id = {31067370}, abstract = {We report here the use of eucalyptol as a bio-based solvent for the Buchwald-Hartwig reaction on O,S,N-heterocycles. These heterocycles containing oxygen, sulfur and nitrogen were chosen as targets or as starting materials. Once again, eucalyptol demonstrated to be a possible sustainable alternative to common solvents.}, keywords = {Buchwald–Hartwig reaction; eucalyptol; bio-based solvent; O,S,N-heterocycles; greener methodology}, year = {2019}, eissn = {2073-4344} } @article{MTMT:31067373, title = {Copper Immobilized on Isonicotinic Acid Hydrazide Functionalized Nano-Magnetite as a Novel Recyclable Catalyst for Direct Synthesis of Phenols and Anilines}, url = {https://m2.mtmt.hu/api/publication/31067373}, author = {Ghiasbeigi, Elahe and Soleiman-Beigi, Mohammad}, doi = {10.1002/slct.201803770}, journal-iso = {CHEMISTRYSELECT}, journal = {CHEMISTRYSELECT}, volume = {4}, unique-id = {31067373}, issn = {2365-6549}, abstract = {A new nano-catalyst which contains a core of magnetic Fe3O4 nanoparticles (NPs) has been fabricated. It is covered via isonicotinic acid hydrazide and copper (Cu). In this sense, Isonicotinic acid hydrazide (INH) is applied because of its ability as a bidendental ligand and pharmaceutical activity in order to be used for the complexion and connection of Cu on Fe3O4 surface for the synthesis of Fe3O4@INH@Cu (INH= Isonicotinic acid hydrazide). In this regard, Fe3O4@INH@Cu as a heterogeneous nanocatalyst for the cross-coupling of aryl halides with potassium hydroxide (KOH) as the hydroxide source and ammonium acetate (NH4OAc), as the amine source in the presence of cesium carbonate (Cs2CO3) in polyethylene glycol (PEG-400), has been applied. The catalyst is a new magnetically recyclable catalytic system with easy preparation and purification, high activity, eco-friendly and economic advantages.}, keywords = {AMINES; phenol; ammonium acetate; cross coupling; Isonicotinic acid hydrazide}, year = {2019}, eissn = {2365-6549}, pages = {3611-3619}, orcid-numbers = {Soleiman-Beigi, Mohammad/0000-0002-7805-5066} } @article{MTMT:31067371, title = {Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas}, url = {https://m2.mtmt.hu/api/publication/31067371}, author = {Scattolin, Thomas and Bouayad-Gervais, Samir and Schoenebeck, Franziska}, doi = {10.1038/s41586-019-1518-3}, journal-iso = {NATURE}, journal = {NATURE}, volume = {573}, unique-id = {31067371}, issn = {0028-0836}, abstract = {Amides and related carbonyl derivatives are of central importance across the physical and life sciences(1,2). As a key biological building block, the stability and conformation of amides affect the structures of peptides and proteins as well as their biological function. In addition, amide-bond formation is one of the most frequently used chemical transformations(3,4). Given their ubiquity, a technology that is capable of modifying the fundamental properties of amides without compromising on stability may have considerable potential in pharmaceutical, agrochemical and materials science. In order to influence the physical properties of organic molecules-such as solubility, lipophilicity, conformation, pK(a) and (metabolic) stability-fluorination approaches have been widely adopted(5-7). Similarly, site-specific modification with isosteres and peptidomimetics(8), or in particular by N-methylation(9), has been used to improve the stability, physical properties, bioactivities and cellular permeabilities of compounds. However, the N-trifluoromethyl carbonyl motif-which combines both N-methylation and fluorination approaches-has not yet been explored, owing to a lack of efficient methodology to synthesize it. Here we report a straightforward method to access N-trifluoromethyl analogues of amides and related carbonyl compounds. The strategy relies on the operationally simple preparation of bench-stable carbamoyl fluoride building blocks, which can be readily diversified to the corresponding N-CF3 amides, carbamates, thiocarbamates and ureas. This method tolerates rich functionality and stereochemistry, and we present numerous examples of highly functionalized compounds-including analogues of widely used drugs, antibiotics, hormones and polymer units.}, year = {2019}, eissn = {1476-4687}, pages = {102-107}, orcid-numbers = {Schoenebeck, Franziska/0000-0003-0047-0929} } @article{MTMT:31067369, title = {Transformations of 3-acyl-4H-polyfluorochromen-4-ones under the action of amino acids and biogenic amines}, url = {https://m2.mtmt.hu/api/publication/31067369}, author = {Shcherbakov, Konstantin V. and Artemyeva, Mariya A. and Burgart, Yanina V. and Evstigneeva, Natalya P. and Gerasimova, Natalya A. and Zilberberg, Natalia V. and Kungurov, Nicolai V. and Saloutin, Victor I. and Chupakhin, Oleg N.}, doi = {10.1016/j.jfluchem.2019.109354}, journal-iso = {J FLUORINE CHEM}, journal = {JOURNAL OF FLUORINE CHEMISTRY}, volume = {226}, unique-id = {31067369}, issn = {0022-1139}, abstract = {For the first time 6,7,8-trifluoro- and 5,6,7,8-tetrafluorinated 3-benzoylflavones have been obtained. Their reactions with amino acids and biogenic amines were studied in comparison with polyfluorinated 3-acetyl-2-methylchromones. For chromones, reactions at the C-2 are preferred, which lead to the pyrone ring opening to form N-substituted aminoenketones. Whereas in the case of flavones the main route is the nucleophilic aromatic substitution of the fluorine atom at the C-7. Flavones and chromones react in the same way both with dopamine to give aminoenketones, and with proline to form 7-amino-substituted chromen-4-ones. All the reactions of chromen-4-ones are accompanied by deacylation, except ones of flavones with proline. Among the synthesized aminoenketones, compounds with high antimycotic and antibacterial action were found.}, keywords = {AMINES; NUCLEOPHILIC AROMATIC SUBSTITUTION; deacylation; 3-acyl-4H-polyfluorochromen-4-ones; Pyrone ring opening; Antimycotic and antibacterial activity}, year = {2019}, eissn = {1873-3328} } @article{MTMT:30965445, title = {Synthesis of Flavone Derivatives through Versatile Palladium-Catalyzed Cross-Coupling Reactions of Tosyloxy- and Mesyloxyflavones}, url = {https://m2.mtmt.hu/api/publication/30965445}, author = {Yuen, On Ying and Pang, Wai Hang and Chen, Xiangmeng and Chen, Zicong and Kwong, Fuk Yee and So, Chau Ming}, doi = {10.1055/s-0037-1611742}, journal-iso = {SYNLETT}, journal = {SYNLETT}, volume = {30}, unique-id = {30965445}, issn = {0936-5214}, abstract = {Tosyloxy- and mesyloxyflavones derived from abundant and biologically important hydroxyflavones were used to synthesize a series of functionalized flavones through versatile palladium-catalyzed cross-coupling reactions. A Pd(OAc) (2) /2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1 H -indole system effectively catalyzed the reactions of a broad range of tosyloxy- and mesyloxyflavones as electrophilic coupling partners with various nucleophiles to give the corresponding products in good to excellent yields. Catalyst loadings of as little as 0.1 mol% Pd were successfully used. Importantly, we demonstrated that this protocol provided a significantly improved efficiency in the synthesis of a potential chromen-4-one-based analogue of a potent inhibitor of DNA-dependent protein kinase.}, keywords = {Mesylates; flavones; CROSS-COUPLING REACTIONS; Palladium catalysis; Phosphine ligands; TOSYLATES}, year = {2019}, eissn = {1437-2096}, pages = {731-737}, orcid-numbers = {So, Chau Ming/0000-0001-6268-651X} } @article{MTMT:27351924, title = {Buchwald-Hartwig reaction: An overview}, url = {https://m2.mtmt.hu/api/publication/27351924}, author = {Heravi, Majid M and Kheilkordi, Zohreh and Zadsirjan, Vahideh and Heydari, Masumeh and Malmir, Masoumeh}, doi = {10.1016/j.jorganchem.2018.02.023}, journal-iso = {J ORGANOMET CHEM}, journal = {JOURNAL OF ORGANOMETALLIC CHEMISTRY}, volume = {861}, unique-id = {27351924}, issn = {0022-328X}, year = {2018}, eissn = {1872-8561}, pages = {17-104} } @article{MTMT:27607161, title = {Modification of Polyfluoro-Containing 3-(Ethoxycarbonyl)flavones by Biogenic Amines and Amino Acids}, url = {https://m2.mtmt.hu/api/publication/27607161}, author = {Shcherbakov, Konstantin V and Burgart, Yanina V and Saloutin, Victor I and Chupakhin, Oleg N}, doi = {10.2174/1570179415666180405120706}, journal-iso = {CURR ORG SYNTH}, journal = {CURRENT ORGANIC SYNTHESIS}, volume = {15}, unique-id = {27607161}, issn = {1570-1794}, year = {2018}, eissn = {1875-6271}, pages = {707-714} } @article{MTMT:30391897, title = {Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules}, url = {https://m2.mtmt.hu/api/publication/30391897}, author = {Shelke, Yogesh G. and Yashmeen, Afsana and Gholap, Aniket V. A. and Gharpure, Santosh J. and Kapdi, Anant R.}, doi = {10.1002/asia.201801020}, journal-iso = {CHEM-ASIAN J}, journal = {CHEMISTRY-AN ASIAN JOURNAL}, volume = {13}, unique-id = {30391897}, issn = {1861-4728}, abstract = {Homogeneous catalysis plays an important and ubiquitous role in the synthesis of simple and complex molecules, including drug compounds, natural products, and agrochemicals. In recent years, the wide-reaching importance of homogeneous catalysis has made it an indispensable tool for the modification of biomolecules, such as carbohydrates (sugars), amino acids, peptides, nucleosides, nucleotides, and steroids. Such a synthetic strategy offers several advantages, which have led to the development of new molecules of biological relevance at a rapid rate relative to the number of available synthetic methods. Given the powerful nature of homogeneous catalysis in effecting these synthetic transformations, this Focus Review has been compiled to highlight these important developments.}, keywords = {PEPTIDES; carbohydrates; amino acids; synthetic methods; homogeneous catalysis}, year = {2018}, eissn = {1861-471X}, pages = {2991-3013} } @article{MTMT:30322288, title = {Synthesis of 1,3-Azol-2-yl O-Heterocycles by Microwave-Irradiation-Assisted Direct C–H Functionalization}, url = {https://m2.mtmt.hu/api/publication/30322288}, author = {Sipos, Zoltán and Kónya, Krisztina}, doi = {10.1055/s-0037-1611012}, journal-iso = {SYNLETT}, journal = {SYNLETT}, volume = {29}, unique-id = {30322288}, issn = {0936-5214}, abstract = {A microwave-irradiation-assisted synthesis of novel 1,3-azol-2-yl-substituted O-heterocycles, namely flavones, chromones, coumarins, and chromanones, is reported. Starting from the appropriate bromo derivatives and 1,3-azoles, this palladium and copper co-catalyzed method provides moderate to good yields and excellent regioselectivity. The ligand- and base-free method can be a useful, generally applicable synthetic tool in the formation of new O-heterocycles.}, keywords = {arylation; microwave heating; Palladium catalysis; O-Heterocycles; azoles; copper catalysis}, year = {2018}, eissn = {1437-2096}, pages = {2412-2416} }