1,1-{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide

Martins Rucins, Martins Kaukulis, Aiva Plotniece, Karlis Pajuste, Nadiia Pikun, Arkadij Sobolev (Coresponding Author)

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Abstract

Synthesis of a double-charged cationic amphiphilic 1,4-dihydropyridine derivative with dodecyl ester groups at positions 3 and 5 of the 1,4-DHP ring was performed starting from Hantzsch type cyclization of dodecyl acetoacetate, 2-naphthaldehyde and ammonium acetate. Bromination of this compound followed by nucleophilic substitution of bromine with (E)-4-(2-(naphthalen-2-yl)vinyl)pyridine gave the desired cationic amphiphilic 1,1-{[3,5-bis(dodecyloxycarbonyl)-4-(naph-thalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide. The obtained target compound was fully characterized by IR, UV,1 H-NMR,13 C-NMR, HRMS and microanalysis. The characterization of the cationic 1,4-DHP nanoparticles in an aqueous solution was performed by DLS measurements. The obtained results showed that the compound formed nanoparticles with an average diameter of around 300 nm, a PDI value of around 490 and a zeta-potential of around 20 mV for freshly prepared samples. However, after one week of storage at room temperature, an aggregation of nanoparticles was detected.

Original languageEnglish
Article numberM1396
JournalMolBank
Volume2022
Issue number3
DOIs
Publication statusPublished - Sep 2022
Externally publishedYes

Keywords*

  • 1,4-dihydropyridines
  • DLS
  • nanoparticles
  • self-assembling properties
  • styrylpyridinium dyes
  • synthetic lipids

Field of Science*

  • 1.4 Chemical sciences
  • 1.6 Biological sciences

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

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