Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
Author:
Keywords:
Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, bioorganic chemistry, fluorine, fused-ring systems, pyridines, ring expansion, HUMAN INTESTINAL FLUIDS, HIV PROTEASE INHIBITORS, PRIVILEGED STRUCTURES, COMBINATORIAL LIBRARIES, MEDICINAL CHEMISTRY, DRUG SOLUBILITY, ANALOGS, 2,4-METHANOPROLINE, SUBSTRUCTURES, PREDICTION, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry
Abstract:
The synthesis and preliminary ADME evaluation of -novel 4-(trifluoromethyl)-5,7,8,9-tetrahydro-6H-pyrido[3,2-b]azepin-6-ones is presented. The key step is a ring expansion of 4-(trifluoromethyl)-7,8- dihydroquinolin-5(6H)-ones via a Beckmann rearrangement. The rearrangement opens up possibilities to access novel unexplored scaffolds for medicinal chemistry. The biopharmaceutical profiling revealed a strong structural dependency of the druglike properties. © Georg Thieme Verlag Stuttgart . New York.