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Updated: Oct 12, 2026

Antibiotic Dereplication Using the Antibiotic Resistance Platform
Published on: October 17, 2019
[Interesting new rearrangements of the cephalosporin antibiotics]
T Gunda1, N S Gabriella, L Tamás
1KLTE-MTA Gyógyszerészi Kémiai Tanszék. tamasgunda@tigris.klte.hu
Abstract:
On the course of the preparation of new cephalosporin derivatives with potential HLE inhibiting activity, three new rearrangements were observed. When a 7 beta-aminocephem sulfone (prepared in situ from 2) was diazotized in methanolic HClO4 solution with HNO2, the triazole 3 was prepared in good yield. On the other hand, the 2 alpha-bromocephem 6 rearranged to two different products, depending on the solvent used. When it was allowed to stay in acetonitrile for 7 days, the bromopyrrol 8 was the product, while in acetone, THF or DMF the aromatic side chain brominated product 7 was obtained. In both cases the inverse polarity of the C-2-Br bond and the easily resulting bromonium ion can be regarded responsible for the rearrangements.
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