Synthesis and characterisation of 1,1'-{[3,5-bis(Dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide

Martins Rucins, Karlis Pajuste, Aiva Plotniece, Nadiia Pikun, Roman Rodik, Sergiy Vyshnevskiy, Arkadij Sobolev (Coresponding Author)

Research output: Contribution to journalArticlepeer-review

Abstract

In the present work, construction of double-charged cationic amphiphilic 1,1-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3). Two-component Hantzsch type cyclisation of dodecyl (E/Z)-3-aminobut-2-enoate (4) and dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3) gave 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5). Bromination of compound 5 followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine 7. The obtained target compound 7 and new intermediates 3, 5 and 6 were fully characterised by IR, UV,1 H NMR,13 C NMR, HRMS or microanalysis. Characterisation of nanoparticles formed by the cationic 1,4-dihydropyridine 7 in an aqueous solution was performed by DLS measurements.

Original languageEnglish
Article numberM1311
JournalMolBank
Volume2022
Issue number1
DOIs
Publication statusPublished - Mar 2022
Externally publishedYes

Keywords*

  • 1,4-dihydropyridines
  • DLS
  • Nanoparticles
  • Self-assembling properties
  • 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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