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

Autor(es)

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: Amino Acids; v. 48, n. 2, p. 445-459, FEB 2016.
• Citações Web of Science: 2

Resumo

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)

• Processo FAPESP: 13/24487-6 - Estudo de reações de síntese limpa e modificação química do biodiesel e óleo fúsel para preparação de carbonatos e carbamatos orgânicos utilizando dióxido de carbono na presença de organocatalisadores e catalisadores heterogêneos
• Beneficiário: Eduardo Rene Perez Gonzalez
• Modalidade de apoio: Auxílio à Pesquisa - Regular