S. Ghannay Synthesis of (3S,3aS,6aS)-2-acetyl-N-methylhexahydrofuro[3,4-d][1,2]oxazole-3-carboxamide via an oxidative cleavage using m-CPBA. ADME approach

Abstract

Novel (3S,3aS,6aS)-2-acetyl-N-methylhexahydrofuro[3,4-d][1,2]oxazole-3-carboxamide has been synthesized by oxidative cleavage in the presence of m-CPBA in good yield. The analysis of the 1D and 2D NMR spectra unambiguously confirms the stereochemistry of the synthesized product. Bioinformatic study were carried out for the synthesized compound using Swiss ADME program to get insight of its appropriate ADME properties and to avoid the failure of candidate drugs at the clinical stage. Results show that (3S,3aS,6aS)-2-acetyl-N-methylhexahydrofuro[3,4-d][1,2]oxazole-3-carboxamide was within the range set by Lipinski’s rule of five, displayed higher gastrointestinal absorption and inhibition of all CYP isoforms.