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Title: Synthesis and studies of calcium channel blocking and antioxidant activities of novel 4-pyridinium and/or N-propargyl substituted 1,4-dihydropyridine derivatives
Authors: Rucins, Martins 
Kaldre, Dainis 
Pajuste, Karlis 
Fernandes, Maria A. S. 
Vicente, Joaquim A. F. 
Klimaviciusa, Linda 
Jaschenko, Elina 
Kanepe-Lapsa, Iveta 
Shestakova, Irina 
Plotniece, Mara 
Gosteva, Marina 
Sobolev, Arkadij 
Jansone, Baiba 
Muceniece, Ruta 
Klusa, Vija 
Plotniece, Aiva 
Keywords: 1,4-Dihydropyridines; N-Dodecyl pyridinium; Propargyl substituent; Calcium antagonists; Antioxidant activity; Mitochondrial processes; Structure–activity relationships
Issue Date: 2014
Publisher: Académie des sciences
Serial title, monograph or event: Comptes Rendus Chimie
Volume: 17
Issue: 1
Abstract: The novel 1,4-dihydropyridine derivatives containing the cationic pyridine moiety at the position 4, and the N-propargyl group as a substituent at position 1 of the 1,4-DHP cycle were designed, synthesised, and assessed in biological tests. Among all the novel compounds, the 4-(N-dodecyl) pyridinium group-containing compounds 11 (without the N-propargyl group) and 12 (with the N-propargyl group) demonstrated the highest calcium antagonistic properties against neuroblastoma SH-SY5Y (IC50 about 5–14 mM) and the vascular smooth muscle A7r5 cell (IC50 – 0.6–0.7 mM) lines, indicating that they predominantly target the L-type calcium channels. These compounds showed a slight total antioxidant activity. At concentrations close to those of L-type calcium channel blocking ones, compound 12 did not affect mitochondrial functioning; also, no toxicity was obtained in vivo. The N-propargyl group as a substituent at position 1 of the 1,4-DHP cycle did not essentially influence the compounds’ activity. The 4-(N-dodecyl) pyridinium moiety-containing compounds can be considered as prototype molecules for further chemical modifications and studies as cardioprotective/neuroprotective agents.
ISSN: 1631-0748
Rights: openAccess
Appears in Collections:FCTUC Ciências da Vida - Artigos em Revistas Internacionais

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