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Synthesis of new ionic liquids based on (5Z,9Z)-alkadienoic acids and choline

Ilgiz Ilshatovich Islamov 1
Ilgiz Ilshatovich Islamov
, 
Adelya V Yusupova 1
Adelya V Yusupova
, 
Vladimir Anatol'evich D'yakonov 2
Vladimir Anatol'evich D'yakonov
, 
1 Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
10.1016/j.mencom.2023.01.015
Published 2022-12-26
Communication , Volume 33, Issue 1, 50-52
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Islamov I. I. et al. Synthesis of new ionic liquids based on (5Z,9Z)-alkadienoic acids and choline // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 50-52.
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Islamov I. I., Yusupova A. V., D'yakonov V. A., Dzhemilev U. M. Synthesis of new ionic liquids based on (5Z,9Z)-alkadienoic acids and choline // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 50-52.
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TY - JOUR
DO - 10.1016/j.mencom.2023.01.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.015
TI - Synthesis of new ionic liquids based on (5Z,9Z)-alkadienoic acids and choline
T2 - Mendeleev Communications
AU - Islamov, Ilgiz Ilshatovich
AU - Yusupova, Adelya V
AU - D'yakonov, Vladimir Anatol'evich
AU - Dzhemilev, Usein Memetovich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 50-52
IS - 1
VL - 33
ER -
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@article{2022_Islamov,
author = {Ilgiz Ilshatovich Islamov and Adelya V Yusupova and Vladimir Anatol'evich D'yakonov and Usein Memetovich Dzhemilev},
title = {Synthesis of new ionic liquids based on (5Z,9Z)-alkadienoic acids and choline},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.015},
number = {1},
pages = {50--52},
doi = {10.1016/j.mencom.2023.01.015}
}
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Islamov, Ilgiz Ilshatovich, et al. “Synthesis of new ionic liquids based on (5Z,9Z)-alkadienoic acids and choline.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 50-52. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.015.
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Keywords

(5Z
9Z)-alkadienoic acids
allenes
choline
cross-cyclomagnesiation
Grignard reagents
ionic liquids.
titanocene dichloride

Abstract

Efficient synthesis of ionic liquids based on stereoisomerically pure natural and synthetic higher (5Z,9Z)-alkadienoic acids and choline hydroxide was developed. The key unsaturated carboxylic acids were prepared using the stereoselective cross-cyclomagnesiation reaction of aliphatic and oxygen-containing 1,2-dienes with EtMgBr in the presence of Mg metal and Cp2TiCl2 catalyst.

References

.
Ionic liquids in drug delivery
Shamshina J.L., Barber P.S., Rogers R.D.
Expert Opinion on Drug Delivery, 2013
.
Ionic liquids in pharmaceutical applications.
Marrucho I.M., Branco L.C., Rebelo L.P.
Annual Review of Chemical and Biomolecular Engineering, 2014
.
Biocompatible ionic liquids: fundamental behaviours and applications.
Gomes J.M., Silva S.S., Reis R.L.
Chemical Society Reviews, 2019
.
A large-scale study of ionic liquids employed in chemistry and energy research to reveal cytotoxicity mechanisms and to develop a safe design guide
Dzhemileva L.U., D'yakonov V.A., Seitkalieva M.M., Kulikovskaya N.S., Egorova K.S., Ananikov V.P.
Green Chemistry, 2021
.
Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells
Reiß M., Brietzke A., Eickner T., Stein F., Villinger A., Vogel C., Kragl U., Jopp S.
RSC Advances, 2020
.
Ionic Liquid-Based Materials for Biomedical Applications
Correia D.M., Fernandes L.C., Fernandes M.M., Hermenegildo B., Meira R.M., Ribeiro C., Ribeiro S., Reguera J., Lanceros-Méndez S.
Nanomaterials, 2021
.
The Emerging Role of Ionic Liquid-Based Approaches for Enhanced Skin Permeation of Bioactive Molecules: A Snapshot of the Past Couple of Years
Gomes A., Aguiar L., Ferraz R., Teixeira C., Gomes P.
International Journal of Molecular Sciences, 2021
.
Ionic-Liquid-Based Paclitaxel Preparation: A New Potential Formulation for Cancer Treatment
Chowdhury M.R., Moshikur R.M., Wakabayashi R., Tahara Y., Kamiya N., Moniruzzaman M., Goto M.
Molecular Pharmaceutics, 2018
.
Design of Nonsteroidal Anti-Inflammatory Drug-Based Ionic Liquids with Improved Water Solubility and Drug Delivery
Chantereau G., Sharma M., Abednejad A., Neves B.M., Sèbe G., Coma V., Freire M.G., Freire C.S., Silvestre A.J.
ACS Sustainable Chemistry and Engineering, 2019
.
Antiproliferative Organic Salts Derived from Betulinic Acid: Disclosure of an Ionic Liquid Selective Against Lung and Liver Cancer Cells
Silva A.T., Cerqueira M.J., Prudêncio C., Fernandes M.H., Costa-Rodrigues J., Teixeira C., Gomes P., Ferraz R.
ACS Omega, 2019
.
Novel Very Long-Chain α-Methoxylated Δ5,9 Fatty Acids from the SpongeAsteropus nigerAre Effective Inhibitors of Topoisomerases IB
Carballeira N.M., Montano N., Amador L.A., Rodríguez A.D., Golovko M.Y., Golovko S.A., Reguera R.M., Álvarez-Velilla R., Balaña-Fouce R.
Lipids, 2015
.
Transdermal Protein Delivery Using Choline and Geranate (CAGE) Deep Eutectic Solvent
Banerjee A., Ibsen K., Iwao Y., Zakrewsky M., Mitragotri S.
Advanced healthcare materials, 2017
.
The facile synthesis of the 5Z,9Z-dienoic acids and their topoisomerase I inhibitory activity
D'yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.K., Khusnutdinova E.K., Dzhemilev U.M.
Chemical Communications, 2013
.
Cholinium amino acid-based ionic liquids
Le Donne A., Bodo E.
Biophysical Reviews, 2021
.
Antibacterial study and fatty acid analysis of lipids of the sponge Myrmekioderma granulata
Manjari Mishra P., Sree A., Baliarsingh S.
Chemistry of Natural Compounds, 2009
.
A new cytotoxic fatty acid (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid and the sterols from the far Eastern sponge Geodinella robusta
Makarieva T.N., Santalova E.A., Gorshkova I.A., Dmitrenok A.S., Guzii A.G., Gorbach V.I., Svetashev V.I., Stonik V.A.
Lipids, 2002
.
Choline based ionic liquids and their applications in organic transformation
Gadilohar B.L., Shankarling G.S.
Journal of Molecular Liquids, 2017
.
Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro
D'yakonov V.A., Islamov I.I., Dzhemileva L.U., Khusainova E.M., Yunusbaeva M.M., Dzhemilev U.M.
Tetrahedron, 2018
.
Microbial biocompatibility of phosphonium- and ammonium-based ionic liquids
Sivapragasam M., Jaganathan J.R., Levêque J., Moniruzzaman M., Abdul Mutalib M.I.
Journal of Molecular Liquids, 2019
.
Improving dermal delivery of hydrophilic macromolecules by biocompatible ionic liquid based on choline and malic acid
Wu X., Chen Z., Li Y., Yu Q., Lu Y., Zhu Q., Li Y., An D., Qi J., Wu W.
International Journal of Pharmaceutics, 2019
.
Ionic liquids with methotrexate moieties as a potential anticancer prodrug: Synthesis, characterization and solubility evaluation
Moshikur R.M., Chowdhury M.R., Wakabayashi R., Tahara Y., Moniruzzaman M., Goto M.
Journal of Molecular Liquids, 2019
.
New fatty acids from Colombian Caribbean Sea sponges
Rodríguez W., Osorno O., Ramos F.A., Duque C., Zea S.
Biochemical Systematics and Ecology, 2010
.
Oral delivery of sorafenib through spontaneous formation of ionic liquid nanocomplexes
Shi Y., Zhao Z., Gao Y., Pan D.C., Salinas A.K., Tanner E.E., Guo J., Mitragotri S.
Journal of Controlled Release, 2020
.
Improving dermal delivery of hyaluronic acid by ionic liquids for attenuating skin dehydration
Wu X., Zhang H., He S., Yu Q., Lu Y., Wu W., Ding N., Zhu Q., Chen Z., Ma Y., Qi J.
International Journal of Biological Macromolecules, 2020
.
New synthetic analogues of natural 5Z,9Z-dienoic acids: Stereoselective synthesis and study of the anticancer activity
Makarov A.A., Dzhemileva L.U., Salimova A.R., Makarova E.K., Ramazanov I.R., D'yakonov V.A., Dzhemilev U.M.
Bioorganic Chemistry, 2020
.
Makhaeva G.F., Serkov I.V., Kovaleva N.V., Rudakova E.V., Boltneva N.P., Kochetkova E.A., Proshin A.N., Bachurin S.O.
Mendeleev Communications, 2021
.
Advances in the Chemistry of Natural and Semisynthetic Topoisomerase I/II Inhibitors
D'yakonov V.A., Dzhemileva L.U., Dzhemilev U.M.
Studies in Natural Products Chemistry, 2017