TY - JOUR AU - Keglevich, György TI - Preface JF - CURRENT GREEN CHEMISTRY J2 - CURR GREEN CHEM VL - 13 PY - 2026 IS - 1 SP - v EP - v PG - 1 SN - 2213-3461 DO - 10.2174/0122133461425658250707061016 UR - https://m2.mtmt.hu/api/publication/36276528 ID - 36276528 N1 - Export Date: 18 August 2025; Cited By: 0; Correspondence Address: G. Keglevich; Department of Organic Chemical Technology, Budapest University of Technology and Economics, Hungary; email: keglevich.gyorgy@vbk.bme.hu LA - English DB - MTMT ER - TY - JOUR AU - Keglevich, György TI - Preface JF - CURRENT ORGANIC CHEMISTRY J2 - CURR ORG CHEM VL - 30 PY - 2026 IS - 1 SP - iv EP - iv PG - 1 SN - 1385-2728 DO - 10.2174/0113852728434504250811111213 UR - https://m2.mtmt.hu/api/publication/36306983 ID - 36306983 N1 - Export Date: 29 August 2025; Cited By: 0; CODEN: CORCF LA - English DB - MTMT ER - TY - CHAP AU - Szalai, Zsuzsanna AU - Keglevich, György ED - Demadis, Konstantinos D. TI - Synthesis of phosphonates for pharmaceutical applications T2 - Phosphonate Chemistry, Technology, and Applications PB - Elsevier CY - Amsterdam CY - London CY - Cambridge, Massachusetts SN - 9780443333743 PY - 2026 SP - 67 EP - 87 PG - 21 DO - 10.1016/B978-0-443-33374-3.00040-2 UR - https://m2.mtmt.hu/api/publication/36468793 ID - 36468793 N1 - Export Date: 11 March 2026; Cited By: 0; AB - This chapter focuses on the synthesis of phosphonates relevant for pharmaceutical applications due to their real or potential biological activity. The classes of compounds discussed embrace α-hydroxyphosphonates, methylenebisphosphonates, and dronic acid derivatives. The latter species are useful in the treatment of illnesses including osteoporosis or cancer diseases. The Pudovik reaction is the most common method for the synthesis of α-hydroxyphosphonates. Another pathway for their synthesis is the Abramov reaction. In addition, hydroxyphosphonates may be prepared from α-oxophosphonates by reaction with Grignard reagents, or by the oxidation of alkylphosphonates. Additional potentially bioactive compounds may be obtained by the modification of hydroxyphosphonates by acylation, alkylation, nucleophilic substitution, oxidation, rearrangement and hydrolysis. Hydroxy-methylenebisphosphonates may be obtained by the addition reaction of dialkyl phosphites or diarylphosphine oxides to the C=O group of the α-oxophosphonates. Base catalysts, for example, dialkylamines are applied in this reaction. Using less catalyst at a lower temperature, the adduct is the major component, while using more catalyst at a higher temperature, the rearranged product predominates. The outcome may also be influenced by the substitution pattern. Dronic acids are usually prepared from the corresponding carboxylic acid derivative using various phosphorus reagents, such as phosphorus trichloride and phosphorous acid. Methanesulfonic acid (MSA) and sulfolane are the most often used solvents. When using MSA, there is a need only for phosphorus trichloride. On the one hand, it forms a mixed anhydride with the carboxylic acid, on the other hand, it may form an even more active phosphorus reagent in reaction with phosphorus trichloride. In sulfolane, both phosphorus trichloride and phosphorous acid are needed. Phosphorus trichloride reacts with a carboxylic acid to form an acid chloride, and also forms a dimer or a trimer condensate with phosphorous acid. These species react with either the acid chloride or the carboxylic acid, leading to the formation of ketophosphonic acid, which is further transformed via intermediate steps to establish the dronic acid. LA - English DB - MTMT ER - TY - JOUR AU - Bajusz, Bence AU - Karaghiosoff, Konstantin AU - Drahos, László AU - Gömöry, Ágnes AU - Keglevich, György TI - The Synthesis of Bis(α-aryl-methylphosphonoyl)amines by the Microwave-Assisted Catalyst-Free Tandem Kabachnik–Fields Reaction JF - CATALYSTS J2 - CATALYSTS VL - 16 PY - 2026 IS - 2 PG - 17 SN - 2073-4344 DO - 10.3390/catal16020148 UR - https://m2.mtmt.hu/api/publication/36990134 ID - 36990134 N1 - This project was supported by the National Research, Development and Innovation Office/NKKP ADVANCED-149447. Project no. RRF 2.3.1-21-2022-00015 has been implemented with the support provided by the European Union. AB - Potentially biologically active α-aminophosphonic derivatives were prepared by the Kabachnik–Fields condensation of α-amino-α-aryl-methylphosphonates, arylaldehydes, and diethyl phosphite to afford bis(α-aryl-methylphosphonoyl)-amines as a mixture of racemic and meso isomers. To go “green”—performing the transformations under microwave irradiation—there was no need for a catalyst. On the other hand, the phospha-Mannich reaction of α-amino-α-phenyl-methylphosphonate with arylaldehydes led to (α-aryl-methylphosphonoyl)-(α-phenyl-methylphosphonoyl)-amines as a mixture of SS/RR and SR/RS racemates. Moreover, the respective symmetric products with identical aryl groups were also present. The outcome was similar, when α-amino-α-aryl-methyl-phosphonates were condensed with benzaldehyde and diethyl phosphite. The products were analyzed by 1D and 2D NMR spectroscopy. The combined NMR analysis of the products confirmed their structure. LA - English DB - MTMT ER - TY - JOUR AU - Szalai, Zsuzsanna AU - Facskó, Regina AU - Gömöry, Ágnes AU - Drahos, László AU - Tekula, Szilárd AU - Takács, Angéla AU - Kőhidai, László AU - Keglevich, György TI - The Synthesis of α-Hydroxy-Alkylphosphonate Derivatives and Evaluation of Their Cytotoxic Activity JF - PHARMACEUTICALS J2 - PHARMACEUTICALS-BASE VL - 19 PY - 2026 IS - 3 PG - 17 SN - 1424-8247 DO - 10.3390/ph19030396 UR - https://m2.mtmt.hu/api/publication/36994244 ID - 36994244 AB - Background: It is known that the α-hydroxyphosphonates and their derivatives may have potential biological activity. Methods: Within the prominent class of α-hydroxyphosphonates, α-hydroxy-alkylphosphonates and their derivatives were prepared as new representatives in the hope of obtaining biologically active species. During our work the Pudovik reaction, acylation and phosphinoylation/phosphorylation methods were used. The new compounds were characterized by NMR and MS spectroscopy. The antiproliferative effects were tested on U266 (myeloma multiplex) and A2058 (melanoma) cells. Results: Ethyl methyl ketone–dialkyl phosphite and secondary phosphine oxide adducts were synthesized by the Pudovik reaction on the earlier analogy of acetaldehyde– and acetone adducts. The hydroxyphosphonates and hydroxyphosphine oxides were acylated and phosphinoylated/phosphorylated. Due to the steric hindrance in the case of the preparation of the acetone–and ethyl methyl ketone–diethyl phosphite adducts, a two-step procedure was elaborated that was also suitable for the thiophosphinoylation of the adducts. A part of the α-hydroxyphosphonates could be successfully methanesulfonylated. The new derivatives prepared were tested on myeloma and melanoma cells, and it was found that the antiproliferative activity is primarily driven by phosphinoylation, particularly by diphenylthiophosphinoylation. The most promising compound, the diphenylthiophosphinoylated hydroxyphosphine oxide, reduced the viability of the U266 cells to less than 20% after a treatment with 100 µM concentration in a long-term experiment. Conclusions: A subset of the synthesized α-hydroxyphosphonate derivatives exhibited cytotoxic activity, supporting further structural optimization to identify compounds with enhanced biological efficacy. LA - English DB - MTMT ER - TY - JOUR AU - Szalai, Zsuzsanna AU - Szloboda, Kristóf AU - Karaghiosoff, Konstantin AU - Czugler, Mátyás AU - Takács, Angéla AU - Kőhidai, László AU - Gömöry, Ágnes AU - Drahos, László AU - Keglevich, György TI - Cytotoxic Agents by the Phosphinoylation and Thiophosphinoylation of 3-Hydroxy-1,2,3,6-tetrahydrophosphinine 1-Oxides as β-Hydroxyphosphonates and -Phosphine Oxides JF - ACS OMEGA J2 - ACS OMEGA VL - 11 PY - 2026 IS - 9 SP - 14964 EP - 14975 PG - 12 SN - 2470-1343 DO - 10.1021/acsomega.5c11546 UR - https://m2.mtmt.hu/api/publication/37003377 ID - 37003377 AB - A series of hydroxy-1,2,3,6-tetrahydrophosphinine oxides were prepared by the two-step ring enlargement of 1-substituted 3-phospholene 1-oxides via the corresponding dichlorocarbene adducts. The two diastereomers of the P-ethoxy-3-phosphabicyclo[3.1.0]hexane 3-oxides could be identified by single crystal X-ray analysis, hence the isomers could be characterized by NMR methods. Detailed examination of the crystal structures of the two isomers shows weak O & centerdot;& centerdot;& centerdot;H and Cl & centerdot;& centerdot;& centerdot;H interactions, which are different for the two isomers, in accord with the different arrangements of the molecules in the solid state. The less hindered hydroxy-tetrahydrophosphinine oxide isomers were selectively phosphinoylated and thiophosphinoylated. The cytotoxic effect of the P-heterocycles synthesized was tested on U266 myeloma cells and on A2058 melanoma cells. The results are promising, as the viability of the cells was decreased drastically at the higher 100 mu M concentration, especially in respect of one hydroxy-tetrahydrophosphinine oxide and the two P-functionalized derivatives, independently of the substituent's nature. LA - English DB - MTMT ER - TY - JOUR AU - Czugler, Mátyás AU - Mucsi, Zoltán AU - Drabowicz, Józef AU - Keglevich, György TI - Delocalization and geometries in the P-function of thiophosphinic derivatives: tautomerism and supramolecular interactions JF - STRUCTURAL CHEMISTRY J2 - STRUCT CHEM PY - 2026 PG - 12 SN - 1040-0400 DO - 10.1007/s11224-025-02596-2 UR - https://m2.mtmt.hu/api/publication/37063738 ID - 37063738 N1 - Open access funding provided by Budapest University of Technology and Economics. This project was supported by the National Research, Development and Innovation Office (NKKP-ADVANCED 149447). AB - Model series of thiophosphinic acid derivatives were scrutinized at the B3LYP/6-311 + + G(2d,2p) level of theory, and the resulting geometries were compared with experimental crystal structure data obtained from the Cambridge Structure Database (CSD). Typical bond length and bond angle values were selected for a series of similar fragments from CSD, and mean dimensions were also calculated from the experimental data accumulated. Linking the results of theoretical calculations and the evidences of data mining allowed the reconsideration of a few past experimental models with (thio)phosphinate-anion-(thio)phosphinic acid-type associations. It seems also from this survey that thiophosphinic acid derivatives may be suitable vehicles for transgressing boundaries from a single molecule to supramolecular relations and vice versa. The study shows that a few intramolecular distances such as the P-O bond lengths both in the anionic and in the neutral forms may significantly depend on intermolecular contacts as well. The tautomerism involving the thionic acid and thiolic acid forms was studied by theoretical methods at the B3LYP/6-311 + + G(2d,2p) level of theory assuming monomolecular and different bimolecular mechanisms. The shift toward the thionic actor was supported by the kinetic and thermodynamic energetics. LA - English DB - MTMT ER - TY - JOUR AU - Milen, Mátyás AU - John, Tamás Miklós AU - Pollák, Patrik AU - Keglevich, György TI - The Direct Use of Metallic Ore Minerals as Catalysts in Organic Syntheses JF - CURRENT ORGANIC CHEMISTRY J2 - CURR ORG CHEM VL - 29 PY - 2025 IS - 2 SP - 97 EP - 107 PG - 11 SN - 1385-2728 DO - 10.2174/0113852728327246240821061535 UR - https://m2.mtmt.hu/api/publication/35218541 ID - 35218541 N1 - Available online on: 3 September 2024 Funding text: Declared none. LA - English DB - MTMT ER - TY - JOUR AU - Keglevich, György TI - Preface JF - CURRENT ORGANIC CHEMISTRY J2 - CURR ORG CHEM VL - 29 PY - 2025 IS - 1 SP - 1 EP - 1 PG - 1 SN - 1385-2728 DO - 10.2174/138527282901240905145148 UR - https://m2.mtmt.hu/api/publication/35593965 ID - 35593965 LA - English DB - MTMT ER - TY - JOUR AU - Schindler, József AU - Nagy, Dorka AU - Harján, Rebeka AU - Keglevich, György TI - The scale-up of microwave flow syntheses by recirculation: the chlorine-free preparation of walkyl phenyl- H -phosphinates JF - REACTION CHEMISTRY & ENGINEERING J2 - REACT CHEM ENG VL - 10 PY - 2025 IS - 2 SP - 371 EP - 378 PG - 8 SN - 2058-9883 DO - 10.1039/D4RE00527A UR - https://m2.mtmt.hu/api/publication/35606638 ID - 35606638 AB - The MW flow esterification of phenyl- H -phosphinic acids with alcohols at ca. 150 °C in the presence of 5% of [bmim][PF 6 ] afforded target alkyl phenyl- H -phosphinates with productivity of ca. 6–9 g h −1 by applying a recirculating mode of operation. LA - English DB - MTMT ER -