186343-35-1Relevant articles and documents
Stereoselective Synthesis of Enantiopure Oxazolidinones via Biocatalytic Asymmetric Aminohydroxylation of Alkenes
Zhou, Xiao-Ying,Wan, Nan-Wei,Li, Ying-Na,Ma, Ran,Cui, Bao-Dong,Han, Wen-Yong,Chen, Yong-Zheng
supporting information, p. 4343 - 4348 (2021/08/03)
Chiral oxazolidinones are of significance in both medicinal and synthetic chemistry, while preparing these compounds usually involves using expensive starting materials and harsh reaction conditions. Herein, a one-pot biocatalytic cascade process was developed for stereo- and regioselective aminohydroxylation of diverse alkenes by combining styrene monooxygenase and halohydrin dehalogenase, providing an approach to enantiopure oxazolidinones. (Figure presented.).
Design, Synthesis, and Biological Evaluation of a Series of Oxazolone Carboxamides as a Novel Class of Acid Ceramidase Inhibitors
Caputo, Samantha,Di Martino, Simona,Cilibrasi, Vincenzo,Tardia, Piero,Mazzonna, Marco,Russo, Debora,Penna, Ilaria,Summa, Maria,Bertozzi, Sine Mandrup,Realini, Natalia,Margaroli, Natasha,Migliore, Marco,Ottonello, Giuliana,Liu, Min,Lansbury, Peter,Armirotti, Andrea,Bertorelli, Rosalia,Ray, Soumya S.,Skerlj, Renato,Scarpelli, Rita
, p. 15821 - 15851 (2020/12/23)
Acid ceramidase (AC) is a cysteine hydrolase that plays a crucial role in the metabolism of lysosomal ceramides, important members of the sphingolipid family, a diversified class of bioactive molecules that mediate many biological processes ranging from cell structural integrity, signaling, and cell proliferation to cell death. In the effort to expand the structural diversity of the existing collection of AC inhibitors, a novel class of substituted oxazol-2-one-3-carboxamides were designed and synthesized. Herein, we present the chemical optimization of our initial hits, 2-oxo-4-phenyl-N-(4-phenylbutyl)oxazole-3-carboxamide 8a and 2-oxo-5-phenyl-N-(4-phenylbutyl)oxazole-3-carboxamide 12a, which resulted in the identification of 5-[4-fluoro-2-(1-methyl-4-piperidyl)phenyl]-2-oxo-N-pentyl-oxazole-3-carboxamide 32b as a potent AC inhibitor with optimal physicochemical and metabolic properties, showing target engagement in human neuroblastoma SH-SY5Y cells and a desirable pharmacokinetic profile in mice, following intravenous and oral administration. 32b enriches the arsenal of promising lead compounds that may therefore act as useful pharmacological tools for investigating the potential therapeutic effects of AC inhibition in relevant sphingolipid-mediated disorders.
Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Bronsted acid
Yamanaka, Takuto,Kondoh, Azusa,Terada, Masahiro
, p. 1048 - 1051 (2015/02/19)
The kinetic resolution of racemic secondary alcohols is a fundamental method for obtaining enantiomerically enriched alcohols. Compared to esterification, which is a well-established method for this purpose, kinetic resolution through enantioselective intermolecular acetalization has not been reported to date despite the fact that the formation of acetals is widely adopted to protect hydroxy groups. By taking advantage of the thermodynamics of acetalization by the addition of alcohols to enol ethers, a highly efficient kinetic resolution of racemic amino alcohols was achieved for the first time and in a practical manner using a chiral phosphoric acid catalyst.
