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The biologically active compound 3-aminopropylsilatrane (a compound with a pentacoordinated silicon atom) underwent an aza-Michael reaction with various acrylates and other Michael acceptors. Depending on the molar ratio, the reaction yielded Michael mono- or diadducts (11 examples) containing functional groups (silatranyl, carbonyl, nitrile, amino, etc.). These compounds were characterized via IR and NMR spectroscopy, mass spectrometry, X-ray diffraction, and elemental analysis. Calculations (using in silico, PASS, and SwissADMET online software) revealed that the functionalized (hybrid) silatranes were bioavailable, druglike compounds that exhibited pronounced antineoplastic and macrophage-colony-stimulating activity. The in vitro effect of silatranes on the growth of pathogenic bacteria (Listeria, Staphylococcus, and Yersinia) was studied. It was found that the synthesized compounds exerted inhibitory and stimulating effects in high and low concentrations, respectively.

Background Natural zeolite heulandite (ZH) has been functionalized with 4-(3-triethoxysilylpropyl)- thiosemicarbazide (TSC) to increase the adsorption capacity of Cu(II), Co(II), and Ni(II) ions. Methods The functionalization is confirmed by nitrogen adsorption/desorption (BET), XRD, 1H, 13C NMR, FT-IR, and SEM-EDX techniques. The thermal stability of the modified zeolite is investigated by the TGA-DSC method. The adsorption of Cu(II), Co(II), and Ni(II) ions with the modified zeolite (ZH-TSC) is studied in one- and multi-ionic aqueous solutions with pH = 5.0. Significant findings The functionalization is accompanied by the significant structural changes in the surface of the zeolite. Grafting of TSC onto the zeolite decreases specific surface area and specific volume of pores and micropores of the material, the zeolite surface becoming more uniform and less porous. The adsorption capacity of ZH-TSC is found to be 0.46 mmol/g (29.5 mg/g), 0.42 mmol/g (24.9 mg/g) and 0.28 mmol/g (16.6 mg/g) for Cu(II), Co(II) and Ni(II), respectively. The adsorption of heavy metal ions on the surface of the modified zeolite ZH-TSC is mainly contributed by the formation of chelate complexes due to the donor-acceptor interaction of metal ions with nitrogen and sulfur atoms of the thiosemicarbazide fragment. Localization of Ni, Co, Cu coincides with the position of the coordination centers. Modified zeolite ZH-TSC can be used in environmental science, engineering, or medicine as an effective adsorbent/entero(hemo) adsorbent of heavy or toxic metals.

Silatranes bearing the aryl(hetaryl)-substituted 1-azadienyl moiety ((Het)ArCH=C(YR) C(H)=N- (Y = O, S)) were synthesized by the reaction of 1-(3-aminopropyl)silatrane with 2-alkoxy- and 2-alkylthio-3-(het)arylpropenals. The structures and stereoisomeric compositions of the synthesized compounds were proved by elemental analysis, IR spectroscopy, 1D 1H, 13C, 15N, 29Si, and 2D NMR experiments, mass spectrometry, and DFT calculations. O-Containing compounds exist exclusively as the 1E,2Z isomers, while S-containing derivatives are the mixtures of the 1E,2Z and 1E,2E stereoisomers. Newly synthesized chalcogen-containing poly-functional compounds represent the promising building blocks for design and synthesis of advanced materials and pharmaceuticals.

Increased interest in carbofunctional organosilicon monomers (silanes) and polymers (silsesquioxanes) is associated with the fact that these compounds are promising reagents and building blocks, materials for micro-electronics, agriculture and medicine, complexones, catalysts, and efficient sorbents. Thus, functional polysilsesquioxanes surpass mineral and organic sorbents in sorption properties. Moreover, they have the highest chemical and thermal stability. Along with sorption activity carbofunctional organosilicon compounds of both monomeric and polymeric structures can possess metallochromic properties. All this paves the way for the large-scale development of analytical systems for the creation of new complex test methods for the determination, concentration and separation of metals from solutions. In the present study the functional monomer N-[3-(triethoxysilyl)propyl]acetylguanidine 1 was synthesized by the condensation reaction of 1-acetylguanidine and 3-triethoxysilyl-propylamine. Poly-N-[3-silsesquioxanyl) propyl]acetylguanidine 2 was obtained by hydrolytic polycondensation of compound 1. The composition and structure of compounds 1 and 2 were confirmed by IR and 1H NMR spectroscopy, as well as by elemental analysis. Polymer 2 was studied as a sorbent for ions of heavy metals, such as Hg (II), and noble metals Ag (I), Au (III), Rh (II), Pd (II), Pt (IV) from solutions of their salts in hydrochloric or nitric acid. For polymer 2, the values of static sorption capacities have been calculated. The latter depend on the nature of the metal and have values from 78 mg/g (for platinum) to 366 mg/g for rhodium. The graphs of the degree of metal extraction depending on the sorption time and acid concentration have been plotted. A sorption mechanism is proposed, which is realized due to the chelate interaction of the metal cation (M+) with the amide groups of compounds 1 and 2. The interaction of monomer 1, in the form of indicator paper, and polymer 2, in the powder form, with salts of the studied metals is accompanied by intense specific coloration (metallochromy). Color tables of the samples after their contact with the Ag (I), Au (III), Pd (II), Pt (IV), Rh (III), Hg (II) salts are given.

A number of biologically active compounds, protatrans with the general formula ArХCH2CO2– · НN+(CH2СН2ОН)3 (А), in which Ar = aryl; Х = O, S, SO, SO2, Se were synthesized. It is the first time that the use of protatrans (А) was suggested, namely of the protatrans 2-Me-С6Н4OCH2CO2– · НN+(CH2СН2ОН)3 (1) and 4-Cl-С6Н4SO2CH2CO2– ·НN+(CH2СН2ОН)3 (2), as stimulants of growth and development of underyearlings of freshwater whitefish hybrid forms. It was concluded that adding microquantities of protatrans 1 and 2 (0,001 %) to the fish feed for the hybrid of lake whitefish and Siberian whitefish increases its viability by 6 %, growth by 10 % and weight by 14 %. Available synthetic biostimulants 1 and 2 can be used for artificial reproduction of freshwater cold-water fish (whitefish, salmon).

A series of biologically active metallatranes and hydrometallatranes was synthesized via the reaction of biogenic triethanolamine with salts or oxides of the essential metals; their toxicity was determined, and the immunotropic and cytotoxic properties were evaluated. Compounds causing immunostimulatory, immunosuppressive, and also competing effects on the immune response were revealed. A pronounced immunosuppressant, 1-oxovanadatran, exhibits a high and selective cytotoxic effect, inhibiting the growth of B16 melanoma cells by 39–80%, but does not affect the tumor cells of L1210 lymphocytic leukemia, P815 mastocytoma, and Lewis lung carcinoma.

A series of novel sulfonamide-bridged silatranes 3,4,6,7 has been synthesized by the reaction of N,N-dichloroarylsulfonamides 1a-d with 1-vinylsilatrane 2 and 1-allylsilatrane 5. The structure of the silatrane-sulfonamide hybrids is characterized by elemental analysis, FT-IR, NMR (1H, 13C, 29Si and 15N) spectroscopy, high-resolution mass spectrometry, and X-ray diffraction analysis. The resulting hybrids 4a-d and 7a-d have been investigated by computational screening via ADMET and PASS. These compounds exhibit drug-like features, bioavailability and may have high enzyme-inhibitory activity. The screening (in vitro) of hybrids 4a,b,d and 7a,b for antimicrobial activities against pathogenic bacterial strains shows that these compounds possess antibacterial properties.

The crystal structure of a new compound Ca(4-ClC6H4SCH2COO)2·Н2О obtained as a part of the study of biologically active metal protatranes is determined by single crystal X-ray diffraction. The coordination polyhedron of the calcium atom is heptacoordinated; the interatomic distances and atomic packing in the unit cell are analyzed.

Methods for the synthesis of 4-chlorophenylsulfonylacetic acid and its tris(2-hydroxyethyl)ammonium salt (“sulfacetamine”) were studied. The results of in vitro and in vivo experiments showed that sulfacetamine possesses high antithrombotic, antioxidant, hypocholesterolemic, immunostimulating, and protective-adaptive activities.

Difficultly accessible 1-R-indol-3-ylsulfanyl(sulfonyl)acetic acids 1-R-IndYCH2CO2H (R = H, Me, Bn; Y = S, SO2) 1a–Id were prepared. Their reaction with tris(2-hydroxyethyl)amine yielded tris(2-hydroxyethyl) ammonium 1-R-indol-3-ylsulfanyl(sulfonyl)aceetates (protatranes) 2a–2d. The immunoactive properties of 2a–2d were studied. Protatranes 2a, 2c, and 2d proved to be effective immunosuppressive agents (up to 99.5% inhibition of mice splenocyte proliferation in vitro).

Sulfones are known to be biologically active compounds. X-ray diffraction is used to determine the crystal and molecular structure of methyl-(4-chlorophenyl)sulfone. The closest molecules are in pairs oriented to each other by their chlorine atoms. The crystal architecture is formed by endless ribbons of paired associates of the molecules under study.

A number of tris(2-hydroxyethyl)ammonium arylchalcogenylacetates ArYCH2CO2–• •HN+(CH2CH2OH)3 (1—4) (Ar = aryl; Y = O, S, SO2) were synthesized. Their structure was established by IR and 1H, 13C, 15N NMR spectroscopy. The influence of compounds 1—4 on the growth and development of yeast fungi Saccharomyces cerevisiae was studied. Compounds 1—4 were found to be efficient, safe, and available synthetic stimulants of these processes. The use of compounds 1—4 in low concentrations (from 10–8 to 10–4 wt.%, depending on the time of cultivation, concentration, and the anion type) reduced the lag-phases of development and increased the generation rate of yeast cells by 2—5 times. The amount of yeast cells increased by 2—3 times, while the content of protein in the biomass increased by 13—15%. The fermentation of sugar- and starch-containing raw material with yeast Saccharomyces cerevisiae increased the yield of ethyl alcohol (biofuel) by 5—9%.

Monomeric and polymeric organosilicon derivatives of 1-acetylguanidine, which exhibits sorption properties, were synthesized. The organosilicon polymers prepared were studied as sorbents for heavy [Hg(II)] and noble [Ag(I), Au(III), Rh(III), Pd(II), Pt(IV)] metals. They actively take up platinum group metals and exhibit metallochromic properties by analogy with the starting compound, 1-acetylguanidine. Their interaction with all the elements studied is accompanied by coloration. The initial monomers exhibit similar metallochromic properties.

Physiologically and pharmacologically active het(aryl)chalcogenylacetates of tris(2-hydroxyethyl)ammonium of pharmacopeial purity have been synthesized by the reaction of het(aryl)chalcogenylacetic acids with sodium (potassium) hydroxide and triethanolamine hydrochloride by one-pot method in quantitative yield (up to 99.8%).

Highlights • We have synthesized a wide range of tris-(2-hydroxyethyl)ammonium arylchalcogenylacetates, “protatranes”. • “Protatranes” are growth stimulators of hydrocarbon-oxidizing Rhodococcus erythropolis bacteria isolated from Lake Baikal. • The effect of “protatranes” on growth of Pseudomonas fluorescens is less obvious. • The effect of stimulants on Rhodococcus erythropolis is likely due to the structure of protatranes and the cell wall of bacteria., Under natural conditions, biodegradation processes proceed slowly, especially in regions with low temperature. To activate vital processes in hydrocarbon-oxidizing microorganisms at low temperatures, biologically active compounds can be employed as growth stimulants. A low-temperature (10 °C) study has shown that tris-(2 hydroxyethyl) ammonium arylchalcogenylacetates, “protatranes” exert an effect on the growth of hydrocarbon-oxidizing strains of Rhodococcus erythropolis and Pseudomonas fluorescens, isolated from natural oil seepage on Lake Baikal. It has been found that “protatranes”, at microconcentrations, increase the growth rate of R. erythropolis bacteria by 2–16 times. It has been established that compounds slightly effect the growth of P. fluorescens. The positive effect of “protatranes” compounds on the growth rate of hydrocarbon-oxidizing microorganisms at low positive temperatures can be used for the development of environmentally benign methods for the restoration of natural objects after their contamination with oil.

New organosilicon derivatives of dithizone with high sorption activity and nonselective metallochromic properties were synthesized. When they are modified, the possibility of increasing the selectivity of their metallochromic effect and prospects for using them as test systems are shown.

According to the 1Н, 13С, and 15N NMR spectral data, metallated alkanolammonium ionic liquids exist as equilibrium of mono-, bi-, and tricyclic structures under the biomimetic conditions (Н2О, 25 °C). The equilibrium shift depends on the metal nature and affects the change of all parameters in the NMR spectra.

New potentially pharmacologically active complexes of general formula n[(HOCH2CH2)3N—O]·MX2 (M = Zn, Co, Ni, Cu; X = Cl, MeCO2, ArOCH2CO2; n = 1, 2) were synthesized by the reaction of triethanolamine N-oxide with essential metal salts.

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 (1H, 13C) 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 review summarizes the data on the synthesis, physicochemical properties, structure, and pharmacological activity elucidation of salts and ionic liquids synthesized based on 2-hydroxyethylamines, aryl chalcogenylacetic acids, and essential metals. The practical application prospects of these novel compounds in medicine and biotechnology are discussed.

By X-ray diffraction the crystal and molecular structure of N-methyl-bis(2-hydroxyethyl)ammonium (4-chlorphenylsulfonyl)acetate 4-ClC6H4SO2CH2COO−·CH3N+H(CH2CH2OH)2 synthesized by the interaction of (4-chlorphenylsulfonyl)acetic acid with N-methyl-bis(2-hydroxyethyl)amine is studied.

Methods for the synthesis of 4-chlorophenylsulfonylacetic acid and its tris-(2-hydroxyethyl)ammonium salt (sulfacetamine) were developed. Results of in vitro and in vivo experiments showed that sulfacetamine possessed high antithrombotic, membrane-stabilizing, antioxidant, hypocholesterolemic, and adaptogenic activity with low toxicity to animals.

The interaction of ethanolamines Me 3− n N(CH 2 CH 2 OH) n ( n = 1–3) with arylheteroacetic acids Ar Y CH 2 COOH (Ar = 2-CH 3 C 6 H 4 , 4-ClC 6 H 4 ; Y = O, S, SO 2 ) as well as acetic acid itself has been studied. For isolated state, the geometries and electronic structures of the complexes obtained were calculated using DFT method at B3LYP/6-311+G ** level of theory. The energy of the compounds has been calculated by means B3LYP/6-311+G ** and MP2/6-311+G ** //B3LYP/6-311+G ** methods. It has been shown that proton transfer (PT) and hydrogen bonding (HB) complexes are formed from triethanolamine (TEA) and the studied acids, while only НВ complexes is generated from diethanolamine and ethanolamine derivatives. The TEA complexes are stabilized by N H + ⋯O − (PT) or O Н⋯N (HB) hydrogen bonds and O H⋯O bonds of its hydroxyl groups and oxygen atoms of acid. The N H + ⋯О − and О H⋯N bonds in the complexes have a partial covalent character as predicted by the quantum theory of atoms in molecule (QTAIM). According to the second-perturbation energies E (2) in the NBO scheme, highest charge transfer is along the О H⋯N hydrogen bond for HB complexes of TEA with Ar Y CH 2 COOH. The GIAO calculated 15 N NMR chemical shifts are well correlated with NBO electron charges on the nitrogen atom for both type complexes.

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.

According to the data of the 15N NMR, IR spectroscopy, and quantum-chemical calculations the products of interaction of chlorides of biogenic metals MCl2 (M = Zn, Ni, Ca) with triethanolammonium salts of acetic and p-chlorophenylsulfanylacetic acids are complexes formed by metal di(p-chlorophenylsulfanylacetates) with protonated triethanolamine via the coordination bonds M…OH.

Quaternary ammonium salts 2(RCH2COO)−·(2H·DACE)+ were synthesized in up to 98% yield by the reaction of biologically active organylheteroacetic acids (OHA) RCH2COOH with diaza-18-crown-6 ether (DACE).

A series of two- and three-component complexes was synthesized of triethanolamine with zinc salts of organylheteroacetic acids, promising biologically active compounds for the search for immunomodulating, antistressor, antitumor, etc. drugs.

New method of synthesis of tris(2-hydroxyethyl)ammonium salts, 2,8,9-trihydroprotatranes X-[HN(CH2CH2OH)3]+, based on the reaction of tris(2-hydroxyethyl)amine (triethanolamine) with ammonium salts NH4X (X = F, Cl, Br, I, NO3, ClO4) was developed. 1H, 13C, 15N NMR and IR spectra of these protatranes were investigated, as well as those of their analogs with X = RCH2COO (R = H; 2-MeC6H4O; 2-Me-4ClC6H3O; 2-MeC6H4S; 4-ClC6H4S; 4-ClC6H4SO2; 3-IndS; 3-(PhCH2-IndS) prepared from the corresponding acids RCH2COOH and triethanolamine. The parameters of IR and NMR spectra of the studied protatranes were governed by the nature of substituent X, which also determined the character of the intra and intermolecular hydrogen bonds NH⋯O and OH⋯O in the protatrane framework.

A series of previously unknown promising biologically active compounds, complexes of biogenic metal salts, aroxyacetic acid salts, and triethanolamine, were prepared. The structure and acid-base properties of these compounds were studied by NMR and IR spectroscopy and by potentiometric titration.

A series of complexes of triethanolamine with metal salts of aroxyacetic acids has been prepared. The complexes are perspective biologically active compounds for search for new immunomodulating, antistress, anti-inflammatory and other types of agents. The structure and acid-base properties of these compounds were studied by NMR and IR spectroscopy and potentiometric titration.

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.

New potentially pharmacologically active tris(2-hydroxyethyl)hydroxyammonium salts were synthesized by the reaction of triethanolamine N-oxide with biologically active acetic acid derivatives RYCH2CO2H (R = Ar, 3-indolyl; Y = O, S, SO2).

Zinc di-(4-chlorphenylthioacetate) dihydrate (4-ClC6H4SCH2COO)2Zn·2H2O (ZTD) is obtained in the reaction of protatrane 4-chlorphenylthioacetate 4-ClC6H4SCH2COOs-2·N+H(CH2CH2OH)3 with zinc dichloride (ZnCl2) in aqueous alcohol. X-ray diffraction is used to study the crystal structure of ZTD and compare it with related compounds. All intermolecular O…O contacts of the neighboring zinc polyhedra are short in ZTD molecules. Apparently, the short intermolecular O…O contacts cause distortions of the octahedral environment of the zinc atom.

The reaction of pharmacological active protic ionic liquid tris-(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate H+N(CH2CH2OH)3 ∙ (-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 ∙ [M(OOCCH2SC6H4Cl-4)2Cl2]2-, M = Zn (2), Ni (3). By recrystallization from aqueous alcohol compound 2 unexpectedly gives Zn(OOCCH2SC6H4Cl-4)2 ∙ 2H2O (4). Unlike 2, compound 3 gives crystals [N(CH2CH2OH)3]2Ni2+ · [-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).

Acetylcholine, an endogenous neurotransmitter, per forms one of the most vital functions in a living organism by promoting neuromuscular transmission from its brain and central nervous system to effector organs. This com pound has ionic liquid structure and is commonly used as the chloride (MeCOOCH2CH2N Me3)•Cl –, which is the first representative of so called cholinomimetics. The drugs of this group include succinic (succinylchol ine, Quelicin) and carbamic acid esters (carbacholine).1 Another group of drugs that block cholinergic transmission is constituted by cholinolytics containing aryl substitu ents in the ester group. They include [2 (2 hydroxy 2,2 diphenylacetoxy)ethyl]trimethylammonium iodide [Ph2C(OH)COOCH2CH2N Me3]•I – (metacin), spas molytin, arpenal, and thiphen.1 In the present work, starting from (2 hydroxyethyl) dimethylamine (1) and various acyl chlorides RC(O)Cl (R = 2 methylphenoxymethyl (2), 4 chlorophenylsul fanylmethyl (3), 4 chlorophenylsulfonylmethyl (4), indol 3 ylsulfanylmethyl (5), and 1 benzylindol 3 ylsulfanyl methyl (6)2—4), we synthesized new analogs of acetylchol ine with potential biological activity. The products ob tained contain either protonated cations and the Cl– an ion (ionic liquids 7—11, m.p. 75—100 C) or alkylated cations and the I– anion (salts 12—16, m.p. 160—193 C) (Scheme 1).

Nontoxic biologically active 1 organylsilatranes are widely used in medicine and agriculture.1 The first repre sentative of ionic liquids (IL) with the silatranyl fragment [MeEt2N (CH2)3Si(OCH2CH2)3N]•I –, possessing anti microbial and tuberculostatic activity, has been synthe sized 40 years ago by the reaction of 1 (3 diethylamino propyl)silatrane with MeI.2 Later, its analog containing a Me3N + group was obtained, which inhibited invasion of the human lung carcinoma cells A549 in vitro.3 In order to obtain new potentially biologically active IL, we applied mild conditions (15 C, 10 min) to carry out a reaction of 1 (3 aminopropyl)silatrane (1) with acet ic acid (2) and biologically active aryl(hetaryl)oxy (sulfanyl)(sulfonyl)acetic acids 3—7 (Scheme 1). Earlier, we used 2 methylphenyloxy (3), 4 chloro 2 methyl phenyloxy (4), 4 chlorophenylsulfanyl (5), 4 chloro phenylsulfonyl (6), 3 indolylsulfanyl (7) acetic acids and 2 hydroxyethylamines in the development of such medic inal remedies and biological agents as "trecrezan", "chloro crezacin", "sulfacetamine", "indacetamine", etc., which had the structure of (2 hydroxyethyl)ammonium IL: [(HOCH2CH2)nN +H]•[–OOCR]. The latter, being low toxic (LD50 = 1300—6000 mg kg –1), possess antiaggrega tion, membrane stabilizing, antisclerosis, immunomodu lating, adaptogenic, antitumor activity and are protectors from ultrasonic and  irradiation.4—14 Note that acids 3—7, in particular 3, under more dras tic conditions (70—80 C, 6—12 h) cleave the silatrane framework in 1 alkylsilatranes with the formation of IL of different structure: [R(OH)Si(OCH2CH2)2N +(H) CH2CH2OH]•[ OOCCH2OC6H4Me 2]. 15 Compounds 8, 10, and 11 are dense IL, 9, 12, and 13 are low melting powders. All of them are well soluble in water, alco hols, acetone, and chloroform. Their structures were confirmed by 1H and 13C NMR and IR spectroscopy, as well as by elemen tal analysis. IR spectra were recorded on a Varian 3100FT IR75 spectrophotometer, 1H and 13C NMR spectra (in CDCl3) were recorded on a DPX 400 spectrometer (1H, 400.13 MHz; 13C, 101.62 MHz; internal standard HMDS).