Oxetanes in drug discovery: structural and synthetic insights

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

Index: Wuitschik, Georg; Rogers-Evans, Mark; Mueller, Klaus; Fischer, Holger; Wagner, Bjoern; Schuler, Franz; Polonchuk, Liudmila; Carreira, Erick M. Angewandte Chemie - International Edition, 2006 , vol. 45, # 46 p. 7736 - 7739

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Citation Number: 140

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 ...