Beilstein J. Org. Chem.2012,8, 1901–1908, doi:10.3762/bjoc.8.220
for the synthesis of substrates 2.
The synthesis of substrates 18 is depicted in Scheme 6. Initially, the carboxylic group of benzoic acids 13a,b was activated by preparing N-acylbenzotriazoles 14, which were then converted into their α-nitroketones 15 by treatment with nitromethane in the presence of
Beilstein J. Org. Chem.2012,8, 1146–1160, doi:10.3762/bjoc.8.128
. Some of the synthesized compounds were tested against an array of microorganisms and showed antibacterial activity against Bordetella bronchistepica, Micrococcus luteus, and Salmonella typhimurium.
Keywords: antibacterial; cluster analysis; N-acylbenzotriazoles; peptidomimetics; similarity
peptidomimetics capable of facile synthesis; and (iii) to synthesize and biotest promising candidates. A synthetic route seems highly relevant, since N-acylbenzotriazoles have been reported elsewhere [35][36][37] to be stable, easy-to-handle acylating agents and have found numerous applications for advantageous N
Supporting Information File 1 for experimental details).
The methodology used for the regioselective syntheses of S- and N-acylcysteines was developed recently in our group by using N-acylbenzotriazoles under mild reaction conditions [37]. Utilizing this methodology, 35a was coupled with two equiv of free