Oxadiazole isomers : All bioisosteres are not created equal

Goldberg, Kristin and Groombridge, Sam and Hudson, Julian and Leach, Andrew G. and MacFaul, Philip A. and Pickup, Adrian and Poultney, Ruth and Scott, James S. and Svensson, Per H. and Sweeney, Joseph (2012) Oxadiazole isomers : All bioisosteres are not created equal. MedChemComm, 3 (5). pp. 600-604. ISSN 2040-2503

Abstract

Two series of amino-substituted 1,2,4- and 1,3,4-oxadiazole matched compounds were evaluated and found to have significant differences in their various physical and pharmaceutical properties. Experimental and computational techniques suggested that variation in hydrogen bond acceptor and donor strength were responsible for these effects.