Oxetanes in drug discovery: structural and synthetic insights

…, I Parrilla, F Schuler, M Rogers-Evans…

Index: Wuitschik, Georg; Carreira, Erick M.; Wagner, Bjoern; Fischer, Holger; Parrilla, Isabelle; Schuler, Franz; Rogers-Evans, Mark; Mueller, Klaus Journal of Medicinal Chemistry, 2010 , vol. 53, # 8 p. 3227 - 3246

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Citation Number: 141

Abstract

An oxetane can trigger profound changes in aqueous solubility, lipophilicity, metabolic stability, and conformational preference when replacing commonly employed functionalities such as gem-dimethyl or carbonyl groups. The magnitude of these changes depends on the structural context. Thus, by substitution of a gem-dimethyl group with an oxetane, aqueous solubility may increase by a factor of 4 to more than 4000 while reducing the rate of ...