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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Mass spectrometry study of N-alkylbenzenesulfonamides with potential antagonist activity to potassium channels

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Author(s):
Martins, Carina C. [1] ; Zanutto Bassetto, Jr., Carlos A. [1] ; Santos, Jandyson M. [2] ; Eberlin, Marcos N. [2] ; Magalhaes, Alvicler [3] ; Varanda, Wamberto [4] ; Perez Gonzalez, Eduardo R. [1]
Total Authors: 7
Affiliation:
[1] Univ Estadual Paulista UNESP, Fac Ciencias & Tecnol, Dept Fis Quim & Biol, Lab Quim Organ Fina, CP 467, BR-19060900 Presidente Prudente, SP - Brazil
[2] Univ Estadual Campinas, UNICAMP, Inst Chem, ThoMSon Mass Spectrometry Lab, BR-13083970 Campinas, SP - Brazil
[3] Univ Estadual Campinas, UNICAMP, Inst Quim, Dept Quim Inorgan, BR-13083970 Campinas, SP - Brazil
[4] Univ Sao Paulo, Sch Med Ribeirao Preto, Dept Physiol, BR-14049900 Ribeirao Preto, SP - Brazil
Total Affiliations: 4
Document type: Journal article
Source: Amino Acids; v. 48, n. 2, p. 445-459, FEB 2016.
Web of Science Citations: 2
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. (AU)

FAPESP's process: 13/24487-6 - Study of reactions of clean synthesis and chemical modification of the biodiesel and fusel oil for preparation of organic carbonate and carbamates using carbon dioxide in the presence of organocatalysts and heterogeneous catalysts
Grantee:Eduardo Rene Perez Gonzalez
Support Opportunities: Regular Research Grants