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The reaction of pharmacological active protic ionic liquid tris-(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate H + N(CH 2 CH 2 OH) 3 ∙ ( - OOCCH 2 SC 6 H 4 Cl-4) (1) with zinc or nickel chloride in a ratio of 2:1 affords stable at room temperature powder-like adducts [H + N(CH 2 CH 2 OH) 3 ] 2 ∙ [M(OOCCH 2 SC 6 H 4 Cl-4) 2 Cl 2 ] 2- , M = Zn (2), Ni (3). By recrystallization from aqueous alcohol compound 2 unexpectedly gives Zn(OOCCH 2 SC 6 H 4 Cl-4) 2 ∙ 2H 2 O (4). Unlike 2, compound 3 gives crystals [N(CH 2 CH 2 OH) 3 ] 2 Ni 2+ · [ - OOCCH 2 SC 6 H 4 Cl-4] 2 (5), which have a structure of metallated ionic liquid. The structure of 5 has been proved by X-ray diffraction analysis. It is the first example of the conversion of a protic ionic liquid into potentially biological active metallated ionic liquid (1 → 3 → 5).
The title compound was prepared by the reaction of 1,4,10,13-tetraoxa-7,16-diazacyclo-octadecane with 4-chloro-2-methyl-phenoxyacetic acid in a ratio of 1:2. The structure has been proved by the data of elemental analysis, IR spectroscopy, NMR ( 1 H, 13 C) technique and by X-ray diffraction analysis. Intermolecular hydrogen bonds between the azonium protons and oxygen atoms of the carboxylate groups were found. Immunoactive properties of the title compound have been screened. The compound has the ability to suppress spontaneous and Con A-stimulated cell proliferation in vitro and therefore can be considered as immunodepressant.
Immunoactive ionic liquids (2-hydroxyethyl) ammonium 1-R-indol-3-ylsulfanyl-acetates HN+R1R2(CH2CH2OH)center dot O-(O)CCH2S-Ind-R-3-1(1-5), were synthesized by the reaction of (2-hydroxyethyl)amines with indol-3-ylsulfanylacetic- or 1-benzylindol-3-ylsulfanylacetic acid. 1: R-1 = R-2 = CH2CH2OH, R-3 = H; 2: R-1 =CH3, R-2=CH2CH2OH, R3 = H; 3: R-1 = R-2 = CH3, R-3 = H; 4: R-1 = R-2 = CH2CH2OH, R-3 = CH2C6H5; 5: R-1 = CH3; R-2 = CH2CH2OH; R-3 = CH2C6H5. The structure of each compound was elucidated by IR, NMR H-1, C-13, and N-15 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.
The title compound was prepared by the reaction of 1,4,10,13-tetraoxa-7,16-diazacyclo-octadecane with 4-chloro-2-methyl-phenoxyacetic acid in a ratio of 1:2. The structure has been proved by the data of elemental analysis, IR spectroscopy, NMR ((1)H, (13)C) technique and by X-ray diffraction analysis. Intermolecular hydrogen bonds between the azonium protons and oxygen atoms of the carboxylate groups were found. Immunoactive properties of the title compound have been screened. The compound has the ability to suppress spontaneous and Con A-stimulated cell proliferation in vitro and therefore can be considered as immunodepressant.
The reaction of pharmacological active protic ionic liquid tris-(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate H+N(CH2CH2OH)(3) center dot (-OOCCH2SC6H4Cl-4) (1) with zinc or nickel chloride in a ratio of 2:1 affords stable at room temperature powder-like adducts [H+N(CH2CH2OH)(3)](2) center dot [M(OOCCH2SC6H4Cl-4)(2)Cl-2](2-), M = Zn (2), Ni (3). By recrystallization from aqueous alcohol compound 2 unexpectedly gives Zn(OOCCH2SC6H4Cl-4)(2) center dot 2H(2)O (4). Unlike 2, compound 3 gives crystals [N(CH2CH2OH)(3)](2)Ni2+ center dot [-OOCCH2SC6H4Cl-4](2) (5), which have a structure of metallated ionic liquid. The structure of 5 has been proved by X-ray diffraction analysis. It is the first example of the conversion of a protic ionic liquid into potentially biological active metallated ionic liquid (1 -> 3 -> 5).