Short and Efficient Synthesis of Alkyl- and Aryl-Ortho-Hydroxy-Anilides and their Antibiotic Activity

Jürgen Krauß; Eva Plesch; Sabine Clausen; Franz Bracher

doi:10.3797/scipharm.1401-19

Short and Efficient Synthesis of Alkyl- and Aryl-Ortho-Hydroxy-Anilides and their Antibiotic Activity

Sci Pharm. 2014 Mar 13;82(3):501-17. doi: 10.3797/scipharm.1401-19. Print 2014 Jul-Sep.

Authors

Jürgen Krauß¹, Eva Plesch¹, Sabine Clausen¹, Franz Bracher¹

Affiliation

¹ Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.

Abstract

Ortho-hydroxy-anilides are part of natural products like the new antibiotics platencin (A) and platensimycin (B). An important step in the total synthesis of these antibiotics or their derivatives is the preparation of the o-hydroxy-anilide partial structure. The presented method allows the preparation of o-hydroxy-anilides and o-dihydroxy-anilides from 2-nitrophenol esters in a one-step synthesis without protecting the hydroxy group. Aryl- and alkyl-anilides were prepared following this method as simple analogues of platensimycin (A). The resulting compounds were tested in an agar diffusion assay for their antibiotic potency.

Keywords: Aminolysis; Anilides; Antibiotic activity; Hydrogenation.