610258-34-9Relevant academic research and scientific papers
Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi
Li, Yitao,Yao, Wenqiang,Lin, Jian,Gao, Guoliang,Huang, Chang,Wu, Yang
, p. 121 - 135 (2021/01/05)
Abstract: A novel series of picarbutrazox-inspired oxadiazole hybrids was synthesized and the derivatives’ biological activity against phytopathogenic fungi was investigated. The molecules were designed by retaining the active fragment of tetrazolyl phenyloxime ether of lead compound picarbutrazox, while introducing the potentially active oxadiazole-derived fragment. Bioassay results revealed that some of the title compounds showed potent in vivo antifungal activities to control cucumber downy mildew. Therefore, this novel oxadiazole phenyloxadiazole derivative can be used as a potential antifungal agent to control cucumber downy mildew and other phytopathogenic fungi for crop protection. Graphic abstract: [Figure not available: see fulltext.].
SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents
Del Poeta, Maurizio,Haranahalli, Krupanandan,Lazzarini, Cristina,Mallamo, John,McCarthy, J. Brian,Ojima, Iwao,Pathiranage, Senuri,Sun, Yi,Zambito, Julia
, (2019/09/06)
Recently, the fungal sphingolipid glucosylceramide (GlcCer) synthesis has emerged as a highly promising new target for drug discovery of next-generation antifungal agents, and we found two aromatic acylhydrazones as effective inhibitors of GlcCer synthesis based on HTP screening. In the present work, we have designed libraries of new aromatic acylhydrazones, evaluated their antifungal activities (MIC80 and time-kill profile) against C. neoformans, and performed an extensive SAR study, which led to the identification of five promising lead compounds, exhibiting excellent fungicidal activities with very large selectivity index. Moreover, two compounds demonstrated broad spectrum antifungal activity against six other clinically relevant fungal strains. These five lead compounds were examined for their synergism/cooperativity with five clinical drugs against seven fungal strains, and very encouraging results were obtained; e.g., the combination of all five lead compounds with voriconazole exhibited either synergistic or additive effect to all seven fungal strains.
Aromatic sulfonyl fluorides covalently kinetically stabilize transthyretin to prevent amyloidogenesis while affording a fluorescent conjugate
Grimster, Neil P.,Connelly, Stephen,Baranczak, Aleksandra,Dong, Jiajia,Krasnova, Larissa B.,Sharpless, K. Barry,Powers, Evan T.,Wilson, Ian A.,Kelly, Jeffery W.
supporting information, p. 5656 - 5668 (2013/06/04)
Molecules that bind selectively to a given protein and then undergo a rapid chemoselective reaction to form a covalent conjugate have utility in drug development. Herein a library of 1,3,4-oxadiazoles substituted at the 2 position with an aryl sulfonyl fluoride and at the 5 position with a substituted aryl known to have high affinity for the inner thyroxine binding subsite of transthyretin (TTR) was conceived of by structure-based design principles and was chemically synthesized. When bound in the thyroxine binding site, most of the aryl sulfonyl fluorides react rapidly and chemoselectively with the pK a-perturbed K15 residue, kinetically stabilizing TTR and thus preventing amyloid fibril formation, known to cause polyneuropathy. Conjugation t50s range from 1 to 4 min, ～1400 times faster than the hydrolysis reaction outside the thyroxine binding site. X-ray crystallography confirms the anticipated binding orientation and sheds light on the sulfonyl fluoride activation leading to the sulfonamide linkage to TTR. A few of the aryl sulfonyl fluorides efficiently form conjugates with TTR in plasma. Eleven of the TTR covalent kinetic stabilizers synthesized exhibit fluorescence upon conjugation and therefore could have imaging applications as a consequence of the environment sensitive fluorescence of the chromophore.
Hyperbranched oxadiazole-containing polyfluorenes: Toward stable blue light PLEDs
Xin, Yu,Wen, Gui-An,Zeng, Wen-Jing,Zhao, Lei,Zhu, Xing-Rong,Fan, Qu-Li,Feng, Jia-Chun,Wang, Lian-Hui,Wei, Wei,Peng, Bo,Cao, Yong,Huang, Wei
, p. 6755 - 6758 (2007/10/03)
The synthesis of hyperbranched oxadiazole-containg polyfluores using 'A2 + A2′ + B3' approach based on Suzuki polycondensation was investigated. The molecular structures of the sample polymer were characterized with high-resolution NMR spectroscopy and elemental analysis. The solubility was found to be poor in organic solvents for hyperbranched polymers with higher contents of 2-(4-bromophenyl)-5-(3,5-dibromophenyl)-1,3,4-oxadiazole monomer. The sample polyfluores showed stable blue light emission even after being annealed in the elevated temperatures in the N2 and air.
