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

作者：Mirskova A N^*; Levkovskaya G G; Kolesnikova O P; Perminova O M; Rudyakova E V; Adamovich S N

来源：Russian Chemical Bulletin, 2010, 59(12): 2236-2246.

DOI：10.1007/s11172-010-0384-9

• indole
• indolylsulfanylalkanecarboxylic acids
• indolylsulfonylalkanecarboxylic acids
• triethanolamine
• dimethylethanolamine
• methylethanolamine
• immunomodulators
• antiproliferative activity

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.

• 出版日期2010-12