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
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2022-03
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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.
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Funding Information: Funding: This research was funded by The Joint Ukraine-Latvia R&D Project “Design and study of physicochemical properties and bioactivity of self-assembling calixarene and dihydropyridine hybrids for DNA delivery”, grant number LV-UA/2020/3. Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
Keywords
1,4-dihydropyridines, DLS, Nanoparticles, Self-assembling properties, Synthetic lipids, 1.4 Chemical sciences, 1.6 Biological sciences, 1.1. Scientific article indexed in Web of Science and/or Scopus database, Biochemistry, Physical and Theoretical Chemistry, Organic Chemistry
Citation
Rucins, M, Pajuste, K, Plotniece, A, Pikun, N, Rodik, R, Vyshnevskiy, S & Sobolev, A 2022, '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', MolBank, vol. 2022, no. 1, M1311. https://doi.org/10.3390/M1311