Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access November 1, 2014

Immunoactive ionic liquids based on 2-hydroxyethylamines and 1-R-indol-3-ylsulfanylacetic acids. Crystal and molecular structure of immunodepressant tris-(2-hydroxyethyl)ammonium indol-3-ylsulfanylacetate

Anna N. Mirskova, Sergey N. Adamovich, Rudolf G. Mirskov, Olga P. Kolesnikova and Uwe Schilde
From the journal Open Chemistry

Abstract

Immunoactive ionic liquids (2-hydroxyethyl)ammonium 1-R-indol-3-ylsulfanyl-acetates HN+R1R2(CH2CH2OH) ∙ -O(O)CCH2S-Ind-R3-1 (1-5), were synthesized by the reaction of (2-hydroxyethyl)amines with indol-3-ylsulfanylacetic- or 1-benzylindol-3-ylsulfanylacetic acid. 1: R1 = R2 = CH2CH2OH, R3 = H; 2: R1 = СН3,R2=CH2CH2OH, R3 = H; 3: R1 = R2 = CH3, R3 = H; 4: R1 = R2 = CH2CH2OH, R3 = СH2С6Н5; 5: R1 = СН3; R2 = CH2CH2OH; R3 = СH2С6Н5. The structure of each compound was elucidated by IR, NMR 1H, 13С, and 15N techniques and their composition was confirmed by elemental analysis. The crystal structure of tris-(2-hydroxyethyl) ammonium indol-3-ylsulfanylacetate was investigated by X-ray diffraction analysis. Immunoactive properties of the title compounds were screened.

Graphical Abstract

References

[1] Hough W.L., Smiglak M., Rodrıґguez H., Swatloski R.P., Spear S.K., Daly D.T., et al., New J. Chem., 2007, 31, 1429, DOI: 10.1039/B706677P 10.1039/b706677pSearch in Google Scholar

[2] Fukaya Y., Iizuka Y., Sekihawa K., Ohno H., Green Chem. 2007, 9, 1155, DOI: 10.1039/B706571J 10.1039/b706571jSearch in Google Scholar

[3] Hough W.L., Rogers R.D., Bull. Chem. Soc. Jpn., 2007, 80(12), 2262, DOI:10.1246/bcsj.80.2262 10.1246/bcsj.80.2262Search in Google Scholar

[4] Rodríguez H., Bica K., Rogers R.D., Trop. J. Pharm. Res., 2008, 7, 1011 Search in Google Scholar

[5] Stoimenovski J., MacFarlane D.R., Bica K., Rogers R.D., Pharm. Research., 2010, 27(4), 521, DOI: 10.1007/s11095-009-0030-0 10.1007/s11095-009-0030-0Search in Google Scholar PubMed

[6] Kumar V., Malhotra S.V., in: Malhotra S.V. (Ed.), Ionic Liquid Applications: Pharmaceuticals, Therapeutics and Biotechnology, ACS Symposium Series, Washington, 2010, 1038, 1, DOI: 10.1021/bk-2010-1038.ch001 10.1021/bk-2010-1038.ch001Search in Google Scholar

[7] Petkovic M., Seddon K.R., Rebelo L.P.N., Pereira C.S., Chem. Soc. Rev., 2011, 40(3), 1403, DOI: 10.1039/C004968A 10.1039/C004968ASearch in Google Scholar PubMed

[8] Stoimenovski J., MacFarlane D.R., Chem. Commun., 2011, 47, 11429, DOI: 10.1039/C1CC14314J 10.1039/c1cc14314jSearch in Google Scholar PubMed

[9] Stoimenovski J., Dean P.M., Izgorodina E.I., MacFarlane D.R., Faraday Discuss, 2012, 154, 335, DOI:10.1039/C1FD00071C 10.1039/C1FD00071CSearch in Google Scholar PubMed

[10] Seter M., Thomson M.J., Stoimenovski J., MacFarlane D.R., Forsyth M., Chem. Commun., 2012, 48, 5983, DOI: 10.1039/c2cc32375c 10.1039/c2cc32375cSearch in Google Scholar PubMed

[11] Mirskova A.N., Mirskov R.G., Adamovich S.N., Voronkov M.G., Russ. J. Chemistry for Sustainable Development, 2011, 19, 467 Search in Google Scholar

[12] Mirskova A.N., Levkovskaja G.G., Mirskov R.G., Voronkov M.G., Russ. J. Org Chem., 2008, 44, 1478 10.1134/S1070428008100126Search in Google Scholar

[13] Mirskova A.N., Levkovskaya G.G., Kolesnikova O.P., Perminova O.M., Rudyakova E.V., Adamovich S.N., Russian Chem. Bull., 2010, 59(12), 2236, DOI: 1066-5285/10/5912-2236 10.1007/s11172-010-0384-9Search in Google Scholar

[14] Sheldrick G.M., SHELXS-97: Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997 Search in Google Scholar

[15] Sheldrick G.M., SHELXL-2013, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 2013 Search in Google Scholar

[16] Brandenburg K., DIAMOND, Version 3.1, Crystal Impact, Bonn, 2005 Search in Google Scholar

[17] Levkovskaya G.G., Rudyakova E.V., Mirskova A.N., Russ. J. Org. Chem., 2002, 38, 1478 10.1023/A:1022566202511Search in Google Scholar

Received: 2014-4-15
Accepted: 2014-6-17
Published Online: 2014-11-1

© 2015 Anna N. Mirskova et al.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Scroll Up Arrow