135206-83-6Relevant articles and documents
Decomposition of α-hydroxyaryl ketones and characterization of some unusual products
Gala,Puar,Das,Kugelman,DiBenedetto
, p. 1199 - 1203 (1992)
α-Hydroxyaryl ketones such as 2-hydroxypropiophenone and 1-(2,4- difluorophenyl)-2-hydroxy-1-propanone, the key intermediates in the preparation of antifungal agents, decompose into oxidized, rearranged, and condensed products. These products were isolated and characterized. The possible mechanisms for the formation of the products are discussed.
Identification and Profiling of Hydantoins - A Novel Class of Potent Antimycobacterial DprE1 Inhibitors
Rogacki, Maciej K.,Pitta, Eleni,Balabon, Olga,Huss, Sophie,Lopez-Roman, Eva Maria,Argyrou, Argyrides,Blanco-Ruano, Delia,Cacho, Monica,Vande Velde, Christophe M. L.,Augustyns, Koen,Ballell, Lluis,Barros, David,Bates, Robert H.,Cunningham, Fraser,Van Der Veken, Pieter
supporting information, p. 11221 - 11249 (2019/01/08)
Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-β-d-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.
Stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668)
Saji,Tamoto,Tanaka,Miyauchi,Fujimoto,Ohashi
, p. 1427 - 1433 (2007/10/02)
The stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668) is described. The key step is the selective synthesis of intermediate threo-2-(2,4-difluorophenyl)-2-(1-substituted ethyl)oxirane. threo-2-(2,4-difluorophenyl)-2-(1-methylthioethyl)oxirane was synthesized threo-selectively by the reaction of 1-(2,4-difluorophenyl)-2-methylthio-1-propanone with dimethyloxosulfonium methylide in a heterogeneous media consisting of a hydrophobic solvent and aqueous alkaline solution.