57735-10-1Relevant academic research and scientific papers
Synthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives
Manap, Sevda
, (2021/09/03)
The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde (2) formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (3). Moreov
Synthesis, Antioxidant Activity, Spectroscopic, Electronic, Nonlinear Optical (NLO) and Thermodynamic Properties of 2-Ethoxy-4-[(5-oxo-3-phenyl-1,5-dihydro-1,2,4-triazol-4-ylimino)-methyl]-phenyl-4-methoxybenzoate: A Theoretical and Experimental Study
Medetalibeyoglu, Hilal
, (2021/10/06)
In the present study, the synthesis, antioxidant activity, spectroscopic, electronic, and thermodynamic properties of 2-ethoxy-4-[(5-oxo-3-phenyl-1,5-dihydro-1,2,4-triazol-4-ylimino)-methyl]-phenyl-4-methoxybenzoate (EPM) were examined. The novel 2-ethoxy
4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors
Baud, Damien,Bebrone, Carine,Becker, Katja,Benvenuti, Manuela,Cerboni, Giulia,Chelini, Giulia,Cutolo, Giuliano,De Luca, Filomena,Docquier, Jean-Denis,Feller, Georges,Fischer, Marina,Galleni, Moreno,Gavara, Laurent,Gresh, Nohad,Kwapien, Karolina,Legru, Alice,Mangani, Stefano,Mercuri, Paola,Pozzi, Cecilia,Sannio, Filomena,Sevaille, Laurent,Tanfoni, Silvia,Verdirosa, Federica,Berthomieu, Dorothée,Bestgen, Beno?t,Frère, Jean-Marie,Hernandez, Jean-Fran?ois
, (2020/09/16)
Resistance to β-lactam antibiotics in Gram-negatives producing metallo-β-lactamases (MBLs) represents a major medical threat and there is an extremely urgent need to develop clinically useful inhibitors. We previously reported the original binding mode of 5-substituted-4-amino/H-1,2,4-triazole-3-thione compounds in the catalytic site of an MBL. Moreover, we showed that, although moderately potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one of the six tested MBLs (L1, VIM-4, VIM-2, NDM-1, IMP-1, CphA) with Ki values in the μM to sub-μM range. Several were broad-spectrum inhibitors, also inhibiting the most clinically relevant VIM-2 and NDM-1. Active compounds generally contained halogenated, bicyclic aryl or phenolic moieties at position 5, and one substituent among o-benzoic, 2,4-dihydroxyphenyl, p-benzyloxyphenyl or 3-(m-benzoyl)-phenyl at position 4. The crystallographic structure of VIM-2 in complex with an inhibitor showed the expected binding between the triazole-thione moiety and the dinuclear centre and also revealed a network of interactions involving Phe61, Tyr67, Trp87 and the conserved Asn233. Microbiological analysis suggested that the potentiation activity of the compounds was limited by poor outer membrane penetration or efflux. This was supported by the ability of one compound to restore the susceptibility of an NDM-1-producing E. coli clinical strain toward several β-lactams in the presence only of a sub-inhibitory concentration of colistin, a permeabilizing agent. Finally, some compounds were tested against the structurally similar di-zinc human glyoxalase II and found weaker inhibitors of the latter enzyme, thus showing a promising selectivity towards MBLs.
In vitro antioxidant and antimicrobial properties of some new 4,5-dihydro-1H-1,2,4-triazole-5-ones
Akta?-Yoku?,Yüksek,Gürsoy-Kol,Alpay-Karao?lu
, p. 389 - 396 (2018/09/29)
In this study, 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (3a-3h) reacted with 3-benzenesulfonyloxy-4-methoxybenzaldehyde (1a-1h) to afford eight new 3-alkyl(aryl)-4-(3-benzenesulfonyloxy-4-methoxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triaz
Synthesis, in vitro antimicrobial and antioxidant activities of some new 4,5-dihydro-1h-1,2,4-triazol-5-one derivatives
Yueksek, Haydar,Akyildirim, Onur,Yola, Mehmet L.,Guersoy-Kol, Oezlem,Celebier, Mustafa,Kart, Didem
, p. 470 - 480 (2013/07/26)
A series of compounds derived from 4,5-dihydro-1H-1,2,4-triazol-5-one were synthesized and characterized by spectral data. The 12 new compounds were analyzed for their potential in vitro antioxidant activities by three different methods. Compound 4f showe
Study of antioxidant properties and DNA interaction of some novel 4,5-Dihydro-1H-1,2,4-triazol-5-one derivatives
Arslantas, Ali,Yüksek, Haydar,Gürsoy-Kol, ?zlem,Ocak, Zafer,Tomruk, Zeynep,Calapoglu, Mustafa
scheme or table, p. 3327 - 3334 (2012/07/28)
3-Alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) reacted with 4-benzenesulfonyloxybenzaldehyde (3) to afford the corresponding seven novel 3-alkyl(aryl)-4-(4-benzenesulfonyloxybenzylidenamino)-4,5-dihydro-1H-1,2, 4-triazol-5-ones (4). The ace
Synthesis of novel triazol compounds containing isatin as potential antibacterial and antifungal agents by microwave and conventional methods
Oezil, Musa,Mentese, Emre,Yilmaz, Fatih,Islamoglu, Fatih,Kahveci, Bahittin
experimental part, p. 268 - 271 (2011/10/05)
Microwave irradiation has been used to accelerate the conversion of isatin (1a) and 5-nitroisatin (1b) into their Schiff bases 3-[5′-aryl(alkyl)- 2′,4′-dihydro-1′,2′,4′-triazol-3′-on- 4′-yl]iminoisatin (3a-g) and 3-[5′-aryl(alkyl)-2′,4′- dihydro-1′,2′,4′-triazol-3′-on-4′-yl] imino-5-nitroisatin (4a-g), respectively. Reaction was achieved by microwave-induced technique, which reduced the reaction time drastically and improved the yield when compared to conventional heating. The newly synthesised bases showed moderate antimicrobial activity against the standard bacterial and fungal organisms tested.
Synthesis and in-vitro antioxidant evaluation of some novel 4-(4-substituted) benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones
Yueksek, Haydar,Guersoy-Kol, Oezlem,Kemer, Guel,Ocak, Zafer,Anil, Baris
, p. 325 - 330 (2013/09/24)
3-Alkyl (aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2a-g) were reacted with 4-ethylbenzaldehyde to afford the corresponding 3-alkyl (aryl).4-(4-ethylbenzylidenamino)-4,5-dihydro-1H-1,2.4-triazol-5-ones (3a-g). The acetylation reactions of compound
Synthesis and in vitro antioxidant evaluation of some novel 4, 5-dihydro-1h-1, 2, 4-triazol-5-one derivatives
Gursoy Kol,Yuksek
experimental part, p. 123 - 136 (2011/01/03)
In this study, thirteen novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives were synthesized and characterized by elemental analyses and IR, 1H NMR,13C NMR and UV spectral data. The synthesized compounds were analyzed for their in v
Determination of the protonation constants of some 4-(substituted benzylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones by the potentiometric method in ethanol-water mixtures
Islamoglu, Fatih,Kahveci, Bahittin,Islamoglu, Yahya
, p. 36 - 41 (2008/09/17)
To gain more information about the effect of solvent on 4,5-dihydro-1H-1,2,4-triazol-5-ones, the stoichiometric protonation constants of thirteen triazoles in ethanol-water mixtures were determined at an ionic strength of 0.10MNaCl and at 25.0 ± 0.1°C und
