[2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes
Rachel C. Epplin, Shashwati Paul, Loïc Herter, Christophe Salomé, Erin N. Hancock, Jay F. Larrow, Erich W. Baum, David R. Dunstan, Carol Ginsburg‐Moraff, Thomas C. Fessard, M. Kevin Brown
Abstract
Aromatic ring isosteres and rigidified saturated hydrocarbons are important motifs to enable drug discovery. Herein we disclose [2]-ladderanes as a class of meta-substituted aromatic ring isosteres and rigidified cyclohexanes. A straightforward synthesis of the building blocks is presented along with representative derivatization. Preliminary studies reveal that the [2]-ladderanes offer similar metabolic and physicochemical properties thus establishing this class of molecules as interesting motifs.
Topics & Concepts
CyclohexanesRing (chemistry)DerivatizationChemistryCombinatorial chemistryStereochemistryOrganic chemistryHigh-performance liquid chromatographyAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis