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Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids

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Abstract

A general method for the synthesis of 1-alkyl(allyl)(benzyl)-substituted (indol-3-yl)-sulfanylalkanecarboxylic acids and hexane-1,6-diyl(1,4-phenylenemethylene)bisindol-3-ylsulfanylalkanecarboxylic acids from the corresponding N-substituted indoles and bisindoles, thiourea, iodine, and halogencarboxylic acids was developed. The oxidation of substituted (indol-3-yl)sulfanylalkanecarboxylic acids for the first time afforded their analogs containing the sulfonyl group. New (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)-alkanecarboxylic acids, which are structural analogs of highly active immunomodulators of indacetamin and VILIM, were synthesized. Among the studied (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanylacetic and -sulfonylalkanecarboxylic acids, the compounds exhibiting high dose-dependent antiproliferative activity by the ability to affect the spontaneous and mitogen-stimulated splenocyte proliferation of mice in vitro were found.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    A. N. Mirskova, G. G. Levkovskaya, E. V. Rudyakova & S. N. Adamovich

  2. Research Institute of Clinical Immunology, Siberian Branch of the Russian Academy of Medical Sciences, 14 ul. Yadrintsevskaya, 630099, Novosibirsk, Russian Federation

    O. P. Kolesnikova & O. M. Perminova

Authors
  1. A. N. Mirskova
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  2. G. G. Levkovskaya
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  3. O. P. Kolesnikova
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  4. O. M. Perminova
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  5. E. V. Rudyakova
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  6. S. N. Adamovich
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Correspondence to A. N. Mirskova.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2181–2190, December, 2010.

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Mirskova, A.N., Levkovskaya, G.G., Kolesnikova, O.P. et al. Directed synthesis and immunoactive properties of (2-hydroxyethyl)ammonium salts of 1-R-indol-3-ylsulfanyl(sulfonyl)alkanecarboxylic acids. Russ Chem Bull 59, 2236–2246 (2010). https://doi.org/10.1007/s11172-010-0384-9

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  • DOI: https://doi.org/10.1007/s11172-010-0384-9

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