171628-41-4Relevant articles and documents
Synthesis of thiazolo[2,3-c]-s-triazoles using poly[(4-diacetoxyiodo) styrene]
Liu, Shi-Juan,Zhang, Ji-Zhen,Tian, Guan-Rong,Liu, Ping
, p. 1753 - 1758 (2005)
Arenecarbaldehyde-4-arylthiazol-2-ylhydrazones underwent ring closure with poly[(4-diacetoxyiodo)styrene] (PSDIB) to 3,5-diarylthiazolo[2,3-c]-s-triazoles in dichloromethane. Copyright Taylor & Francis, Inc.
Water-Mediated One-pot Three-Component Synthesis of Hydrazinyl-Thiazoles Catalyzed by Copper Oxide Nanoparticles Dispersed on Titanium Dioxide Support: A Green Catalytic Process
Reddy, G. Trivikram,Kumar,Reddy, N. C. Gangi
, p. 995 - 1006 (2018/01/27)
The present work describes the catalytic activity of copper oxide nanoparticles dispersed on titanium dioxide in water for one-pot synthesis of a library of hydrazinyl-thiazoles via a three-component reaction of various aldehydes/ketones with thiosemicarbazide and different phenacyl bromides. The structure of the synthesized compound, (E)-4-(4-bromophenyl)-2-(2-(4-methoxybenzylidene) hydrazinyl)thiazole is confirmed by single crystal X-ray diffraction studies. The catalyst prepared by a molten-salt method is characterized by X-ray diffraction, field emission scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy, Auger electron spectroscopy and electron spin resonance spectroscopy. The noteworthy advantages of this method include its broad substrate scope, clean reaction profile, short reaction times and high yields at low catalyst loading. Further, the product does not require any chromatographic purification and the method has the potential for large-scale applications in pharmaceutical industries. In addition, the developed catalyst can be recovered and reused for 5 times without significant loss of activity. Mechanistic studies suggest that the reaction begins with the activation of the carbonyl group of both aldehyde/ketone and phenacyl bromide by copper oxide nanoparticles supported on titanium dioxide in water. These studies reveal that the reaction proceeds via the formation of thiosemicarbazone intermediate. (Figure presented.).
Synthesis and biological assessment of novel 2-thiazolylhydrazones and computational analysis of their recognition by monoamine oxidase B
Distinto, Simona,Yá?ez, Matilde,Alcaro, Stefano,Cardia, M. Cristina,Gaspari, Marco,Sanna, M. Luisa,Meleddu, Rita,Ortuso, Francesco,Kirchmair, Johannes,Markt, Patrick,Bolasco, Adriana,Wolber, Gerhard,Secci, Daniela,MacCioni, Elias
, p. 284 - 295 (2012/04/10)
Monoamine oxidase B (MAO-B) is a promising target for the treatment of neurodegenerative disorders. We report the synthesis and the biological evaluation of halogenated derivatives of 1-aryliden-2-(4-phenylthiazol-2-yl) hydrazines. The fluorinated series shows interesting activity and great selectivity toward the human recombinant MAO-B isoform expressed in baculovirus infected BTI insect cells. The multiple crystal structures alignment of the enzyme highlighted pronounced induced fit (IF) adaptations with respect to bound ligands. Therefore, IF docking (IFD) experiments and molecular dynamic (MD) simulations were carried out to reveal the putative binding mode and to explain the experimentally observed differences in the activity of 1-(aryliden-2-(4-(4- chlorophenyl)thiazol-2-yl)hydrazines. The importance of water molecules within the binding site was also investigated. These are known to play an important role in the binding site cavity and to mediate protein-ligand interactions. Detailed analyses of the trajectories provide insights on the chemical features required for the activity of this scaffold. In particular it was highlighted the importance of fluorine atom interacting with the water close to the cofactor and the influence of steric bulkiness of substituents in the arylidene moiety. Free energy perturbation (FEP) analysis confirmed experimental data. The information we deduced will help to develop novel high-affinity MAO-B inhibitors.
