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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dc.contributor.authorRucins, Martins
dc.contributor.authorPajuste, Karlis
dc.contributor.authorPlotniece, Aiva
dc.contributor.authorPikun, Nadiia
dc.contributor.authorRodik, Roman
dc.contributor.authorVyshnevskiy, Sergiy
dc.contributor.authorSobolev, Arkadij
dc.date.accessioned2022-02-01T16:45:01Z
dc.date.available2022-02-01T16:45:01Z
dc.date.issued2022-03
dc.descriptionFunding 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.
dc.description.abstractIn 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.en
dc.description.statusPeer reviewed
dc.format.extent401403
dc.identifier.citationRucins, 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
dc.identifier.doi10.3390/M1311
dc.identifier.issn1422-8599
dc.identifier.urihttps://dspace.rsu.lv/jspui/handle/123456789/7404
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=85121780495&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofMolBank
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject1,4-dihydropyridines
dc.subjectDLS
dc.subjectNanoparticles
dc.subjectSelf-assembling properties
dc.subjectSynthetic lipids
dc.subject1.4 Chemical sciences
dc.subject1.6 Biological sciences
dc.subject1.1. Scientific article indexed in Web of Science and/or Scopus database
dc.subjectBiochemistry
dc.subjectPhysical and Theoretical Chemistry
dc.subjectOrganic Chemistry
dc.titleSynthesis 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) dibromideen
dc.type/dk/atira/pure/researchoutput/researchoutputtypes/contributiontojournal/article

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