150779-90-1Relevant academic research and scientific papers
Chiral disubstituted piperidinyl ureas: A class of dual diacylglycerol lipase-α and ABHD6 inhibitors
Deng, Hui,Van Der Wel, Tom,Van Den Berg, Richard J.B.H.N.,Van Den Nieuwendijk, Adrianus M.C.H.,Janssen, Freek J.,Baggelaar, Marc P.,Overkleeft, Hermen S.,Van Der Stelt, Mario
, p. 982 - 988 (2017)
Inhibitors of diacylglycerol lipases and α,β-hydrolase domain containing protein 6 (ABHD6) are potential leads for the development of therapeutic agents for metabolic and neurodegenerative disorders. Here, we report the enantioselective synthesis and structure activity relationships of triazole ureas featuring chiral, hydroxylated 2-benzylpiperidines as dual inhibitors of DAGLα and ABHD6. The chirality of the carbon bearing the C2 substituent, as well as the position of the hydroxyl (tolerated at C5, but not at C3) has profound influence on the inhibitory activity of both DAGLα and ABHD6, as established using biochemical assays and competitive activity-based protein profiling on mouse brain extracts.
β-Hydroxypiperidinecarboxylates: Additions to the chiral pool from bakers' yeast reductions of β-ketopiperidinecarboxylates
Knight, David W.,Lewis, Neil,Share, Andrew C.,Haigh, David
, p. 3673 - 3683 (2007/10/03)
Reduction of the piperidine keto esters 16-19 using fermenting bakers' yeast provides high yields of the corresponding hydroxy esters 20, 26, 32 and 37 respectively, exclusively as the cis-diastereoisomers and with good levels (≥80%) of enantiomeric enrichment. The relative stereochemistries of the products were deduced from NMR data while the absolute configurations were determined by degradation to known piperidinemethanol derivatives or, in the case of hydroxy ester 37, by homologation to (R)-3-quinuclidinol 41b.
