Please use this identifier to cite or link to this item:
10.3390/M1311
Title: | 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 |
Authors: | Rucins, Martins Pajuste, Karlis Plotniece, Aiva Pikun, Nadiia Rodik, Roman Vyshnevskiy, Sergiy Sobolev, Arkadij |
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 |
Issue Date: | Mar-2022 |
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 |
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. |
Description: | 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. |
DOI: | 10.3390/M1311 |
ISSN: | 1422-8599 |
Appears in Collections: | Research outputs from Pure / Zinātniskās darbības rezultāti no ZDIS Pure |
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