Isoxazole analogues bind the System transporter: Structure–activity relationship and pharmacophore model

…, B Twamley, A Blumenfeld, MI Szabon-Watola…

Index: Patel, Sarjubhai A.; Rajale, Trideep; O'Brien, Erin; Burkhart, David J.; Nelson, Jared K.; Twamley, Brendan; Blumenfeld, Alex; Szabon-Watola, Monika I.; Gerdes, John M.; Bridges, Richard J.; Natale, Nicholas R. Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 1 p. 202 - 213

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Citation Number: 19

Abstract

Analogues of amino methylisoxazole propionic acid (AMPA), were prepared from a common intermediate 12, including lipophilic analogues using lateral metalation and electrophilic quenching, and were evaluated at System xc-. Both the 5-naphthylethyl-(16) and 5- naphthylmethoxymethyl-(17) analogues adopt an E-conformation in the solid state, yet while the former has robust binding at System xc-, the latter is virtually devoid of activity. The ...