89315-80-0Relevant academic research and scientific papers
The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation
Pogrebnoi, Serghei,Radul, Oleg,Stingaci, Eugenia,Lupascu, Lucian,Valica, Vladimir,Uncu, Livia,Smetanscaia, Anastasia,Petrou, Anthi,?iri?, Ana,Glamo?lija, Jasmina,Sokovi?, Marina,Geronikaki, Athina,Macaev, Fliur Z.
, (2022/05/17)
The control of fungal pathogens is increasingly difficult due to the limited number of effective drugs available for antifungal therapy. In addition, both humans and fungi are eukaryotic organisms; antifungal drugs may have significant toxicity due to the inhibition of related human targets. Furthermore, another problem is increased incidents of fungal resistance to azoles, such as fluconazole, ketoconazole, voriconazole, etc. Thus, the interest in developing new azoles with an extended spectrum of activity still attracts the interest of the scientific community. Herein, we report the synthesis of a series of triazolium salts, an evaluation of their antifungal activity, and docking studies. Ketoconazole and bifonazole were used as reference drugs. All compounds showed good antifungal activity with MIC/MFC in the range of 0.0003 to 0.2/0.0006–0.4 mg/mL. Compound 19 exhibited the best activity among all tested with MIC/MFC in the range of 0.009 to 0.037 mg/mL and 0.0125–0.05 mg/mL, respectively. All compounds appeared to be more potent than both reference drugs. The docking studies are in accordance with experimental results.
A New Mode of Operation of Pd-NHC Systems Studied in a Catalytic Mizoroki-Heck Reaction
Astakhov, Alexander V.,Khazipov, Oleg V.,Chernenko, Andrey Yu.,Pasyukov, Dmitry V.,Kashin, Alexey S.,Gordeev, Evgeniy G.,Khrustalev, Victor N.,Chernyshev, Victor M.,Ananikov, Valentine P.
, p. 1981 - 1992 (2017/06/14)
Metal complexes bearing N-heterocyclic carbene (NHC) ligands are typically considered the system of choice for homogeneous catalysis with well-defined molecular active species due to their stable metal-ligand framework. A detailed study involving 19 different Pd-NHC complexes with imidazolium, benzimidazolium, and triazolium ligands has been carried out in the present work and revealed a new mode of operation of metal-NHC systems. The catalytic activity of the studied Pd-NHC systems is predominantly determined by the cleavage of the metal-NHC bond, while the catalyst performance is strongly affected by the stabilization of in situ formed metal clusters. In the present study, the formation of Pd nanoparticles was observed from a broad range of metal complexes with NHC ligands under standard Mizoroki-Heck reaction conditions. A mechanistic analysis revealed two different pathways to connect Pd-NHC complexes to "cocktail"-type catalysis: (i) reductive elimination from a Pd(II) intermediate and the release of NHC-containing byproducts and (ii) dissociation of NHC ligands from Pd intermediates. Metal-NHC systems are ubiquitously applied in modern organic synthesis and catalysis, while the new mode of operation revealed in the present study guides catalyst design and opens a variety of novel opportunities. As shown by experimental studies and theoretical calculations, metal clusters and nanoparticles can be readily formed from M-NHC complexes after formation of new M-C or M-H bonds followed by C-NHC or H-NHC coupling. Thus, a combination of a classical molecular mode of operation and a novel cocktail-type mode of operation, described in the present study, may be anticipated as an intrinsic feature of M-NHC catalytic systems.
Facile Hydrolysis of Nickel(II) Complexes with N-Heterocyclic Carbene Ligands
Astakhov, Alexander V.,Khazipov, Oleg V.,Degtyareva, Evgeniya S.,Khrustalev, Victor N.,Chernyshev, Victor M.,Ananikov, Valentine P.
, p. 5759 - 5766 (2016/01/12)
Metal complexes with N-heterocyclic carbene ligands (NHC) are ubiquitously used in catalysis, where the stability of the metal-ligand framework is a key issue. Our study shows that Ni-NHC complexes may undergo facile decomposition due to the presence of water in organic solvents (hydrolysis). The ability to hydrolyze Ni(NHC)2X2 complexes decreases in the order of NHC = 1,2,4-triazolium > benzimidazolium ≈ imidazolium. Depending on the ligand and substituents, the half reaction time of the complex decomposition may change from several minutes to hours. The nature of the halogen is also an important factor, and the ability for decomposition of the studied complexes decreases in the order of Cl > Br > I. NMR and MS monitoring revealed that Ni-NHC complexes in the presence of water undergo hydrolysis with Ni-Ccarbene bond cleavage, affording the corresponding N,N′-dialkylated azolium salts and nickel(II) hydroxide. These findings are of great importance for designing efficient and recyclable catalytic systems, because trace water is a common contaminant in routine synthetic applications.
Azocoupling of Quaternary 1,2,4-Triazolium Salts to Form 5-p-N,N-Dimethylaminophenylazo-1,2,4-triazolium Salts
Becker, H. G. O.,Hoffmann, Gerda,Gwan, Kim Mun,Knuepfer, L.
, p. 325 - 337 (2007/10/02)
Quaternary 1,2,4-triazolium salts 1 couple easily with p-N,N-dimethylamino-benzenediazonium salts to form azodyes 3 (5-N,N-dimethylaminophenylazo-1,2,4-triazolium salts), preferably under solid-liquid phase transfer conditions using chloroform or methylene chloride and triethylamine or DABCO.Zwitterionic 1,2,4-triazolium salts (anhydro mercapto hydroxide, anhydro hydroxy hydroxide, and anhydro anilido hydroxide ("nitron")) couple as well.The azodyes - as also well known from industrially used types - absorb in the region of 500 nm and have high extinction coefficients.Substituents in 1-, 3- or 4-position of the triazolium ring exert no clear substituent effects.The quaternary 1,2,4-triazolium salts were synthesized according to standard procedures.
