Publications by authors named "Brigita Cekavicus"

The ethoxycarbonylmethyl esters of 1,4-dihydropyridines were directly converted into carbamoylmethyl esters in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in good to excellent yields under mild conditions.

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New amphiphilic pyridine derivatives containing dodecyloxycarbonyl substituents at positions 3 and 5 and cationic moieties at positions 2 and 6 have been designed and synthesised. Compounds of this type can be considered as synthetic lipids. The corresponding 1,4-dihydropyridine (1,4-DHP) derivatives have earlier been proposed as a promising tool for plasmid DNA (pDNA) delivery in vitro.

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The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH···O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.

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Article Synopsis
  • The study focused on synthesizing derivatives of 2,6-dimethyl-4-aryl-1,4-dihydropyridine 3,5-diesters that could be hydrolyzed, since the original compounds could not be.
  • Seven special acyl esters were created and tested for hydrolysis using Candida rugosa lipase, with specific structural features found to enhance stereoselectivity.
  • The most effective derivative yielded a strong enantiomeric ratio, and the configuration of the resulting carboxylic acid was confirmed to be 4R through X-ray crystallography.
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