Preparation of novel anthranilic acids as antibacterial agents. Extensive evaluation of alternative amide bioisosteres connecting the A-and the B-rings

A Thorarensen, BD Wakefield, DL Romero…

Index: Thorarensen, Atli; Wakefield, Brian D.; Romero, Donna L.; Marotti, Keith R.; Sweeney, Michael T.; Zurenko, Gary E.; Rohrer, Douglas C.; Han, Fusen; Bryant Jr., Garold L. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 10 p. 2823 - 2827

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Citation Number: 16

Abstract

In the past few years, a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected amide bioisosteres connecting the A-and the B-rings. The E-alkene provided a rigid analog with equal potency to the corresponding amide. This ...