[2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes
Rachel C Epplin1, Shashwati Paul1, Loïc Herter2
1Department of Chemistry, Indiana University, 800 E. Kirkwood Ave, Bloomington, IN, 47405, USA.
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.
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