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Type: Artigo de periódico
Title: Mass Spectrometry Study Of N-alkylbenzenesulfonamides With Potential Antagonist Activity To Potassium Channels.
Author: Martins, Carina C
Bassetto, Carlos A Zanutto
Santos, Jandyson M
Eberlin, Marcos N
Magalhães, Alvicler
Varanda, Wamberto
Gonzalez, Eduardo R Perez
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: Esi-ms/ms
Mass Spectrometry
Citation: Amino Acids. v. 48, n. 2, p. 445-459, 2016-Feb.
Rights: fechado
Identifier DOI: 10.1007/s00726-015-2099-6
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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