Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/326744
Type: Artigo
Title: Mass Spectrometry Study Of N-alkylbenzenesulfonamides With Potential Antagonist Activity To Potassium Channels
Author: Martins
Carina C.; Zanutto Bassetto
Carlos A.
Jr.; Santos
Jandyson M.; Eberlin
Marcos N.; Magalhaes
Alvicler; Varanda
Wamberto; Perez Gonzalez
Eduardo R.
Abstract: Herein, we report the synthesis and mass spectrometry studies of several N-alkylbenzenesulfonamides structurally related to sulfanilic acid. The compounds were synthesized using a modified Schotten-Baumann reaction coupled with Meisenheimer arylation. Sequential mass spectrometry by negative mode electrospray ionization (ESI(-)-MS/MS) showed the formation of sulfoxylate anion (m/z 65) observed in the mass spectrum of p-chloro-N-alkylbenzenesulfonamides. Investigation of the unexpected loss of two water molecules, as observed by electron ionization mass spectrometry (EI-MS) analysis of p-(N-alkyl)lactam sulfonamides, led to the proposal of corresponding fragmentation pathways. These compounds showed loss of neutral iminosulfane dioxide molecule (M-79) with formation of ions observed at m/z 344 and 377. These ions were formed by rearrangement on ESI(+)-MS/MS analysis. Some of the molecules showed antagonistic activity against Kv3.1 voltage-gated potassium channels.
Subject: N-alkylbenzenesulfonamides
Mass Spectrometry
Esi-ms/ms
Kv3.1
Editor: Springer Wien
Wien
Rights: fechado
Identifier DOI: 10.1007/s00726-015-2099-6
Address: https://link.springer.com/article/10.1007%2Fs00726-015-2099-6
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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