New atranes and similar ionic complexes. Synthesis, structure, properties

Адамович, С. Н.

doi:10.1002/aoc.4940

Cited by 36 publications

(13 citation statements)

References 89 publications

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“…Based on the previous studies on the biological activity, [ 2,4,6 ] it can be assumed that high antibacterial activity against gram‐positive microorganisms is due to the easy binding of the silatranes with receptors on the surface of their microbial cells (Figure 1). Perhaps, lack of activity of compounds 1 , 3d‐f, and 4d‐f toward the gram‐negative microorganisms is caused by peculiarities of the cellular structure of these bacteria.…”

Section: Resultsmentioning

confidence: 99%

“…Trialkanolamine organosilicon esters, silatranes XSi (OCHRCH 2 ) 3 N, belong to a widely known class of tricyclic compounds of pentacoordinated silicon (with intramolecular transannular Si ← N dative bond). [ 1–4 ] The unique structure of silatranes imparts them original chemical and physical properties. Also, unlike other organosilicon compounds (siloxanes, silicones), silatranes possess amazing physiological activity.…”

Section: Introductionmentioning

confidence: 99%

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Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Адамович

Kondrashov

Ushakov

et al. 2020

Applied Organom Chemis

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A new family of mono‐ (3a‐h) and bis‐ (4a‐g) isoxazole‐bridged silatranes has been synthesized by the reaction of 3‐aminopropylsilatrane (1) and 3‐substituted 5‐chloro‐methylisoxazoles (2a‐h). The structure of the isoxazole‐silatrane hybrids is characterized by elemental analysis, FT‐IR, UV, NMR (1H, 13C,29Si and 15N) spectroscopy, high‐resolution mass spectrometry, and X‐ray diffraction analysis. The in silico ADME (absorption, distribution, metabolism, excretion) assessment reveals that properties of mono‐adducts (3a‐h) are similar to those of drugs obeyed to the Lipinski's rule. The calculated screening of potential pharmacological activity profiles (in silico PASS program) of isoxazole‐silatranes shows that all synthesized compounds (both mono‐ and bis‐substituted) may have high antitumor action, unlike starting isoxazoles. The preliminary screening of the synthesized silatranes for antimicrobial activity against Enterococcus durans, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa indicates that all test samples are active only against gram‐positive microorganisms. Silatrane 3f displays minimal inhibitory concentration (MIC 12.5 and 6.2 μg ml−1) against E. durans and B. subtilis as compared with standard drug gentamicin (MIC 25 and 50 μg ml−1).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Адамович

Kondrashov

Ushakov

et al. 2020

Applied Organom Chemis

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“…Recent achievements, challenges and prospects for using atranes are given in the reviews [ 18 , 19 , 20 ]. Atranes, ocanes and hypoatranes contain an intramolecular coordination bond nitrogen→element.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of Reactions of 1-Substituted Silatranes and Germatranes, 2,2-Disubstituted Silocanes and Germocanes, 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes with Alcohols (Methanol, Ethanol): DFT Study

2020

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The mechanism of reactions of silatranes and germatranes, and their bicyclic and monocyclic analogues with one molecule of methanol or ethanol, was studied at the Density Functional Theory (DFT) B3PW91/6-311++G(df,p) level of theory. Reactions of 1-substituted sil(germ)atranes, 2,2-disubstituted sil(germ)ocanes, and 1,1,1-trisubstituted hyposil(germ)atranes with alcohol (methanol, ethanol) proceed in one step through four-center transition states followed by the opening of a silicon or germanium skeleton and the formation of products. According to quantum chemical calculations, the activation energies and Gibbs energies of activation of reactions with methanol and ethanol are close, their values decrease in the series of atranes–ocanes–hypoatranes for interactions with both methanol and ethanol. The reactions of germanium-containing derivatives are characterized by lower activation energies in comparison with the reactions of corresponding silicon-containing compounds. The annular configurations of the product molecules with electronegative substituents are stabilized by the transannular N→X (X = Si, Ge) bond and different intramolecular hydrogen contacts with the participation of heteroatoms of substituents at the silicon or germanium.

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“…В данном контексте перспективны синтезированные нами доступные физиологически активные соединения -протатраны [5][6][7][8][9][10][11][12]. В качестве основы для дизайна протатранов выбраны два вида доступных реактивов (компонентов): биогенные этаноламины (в частности, триэтаноламин) и биологически активные арилхалькогенилуксусные кислоты.…”

Section: Introductionunclassified

Protatrans as biomodulators of <i>Candida ethanolica</i> growth

Кирюхина¹,

Лозовая²,

Privalova³

et al. 2020

Izvestiâ vuzov. Prikladnaâ himiâ i biotehnologiâ

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This study was aimed at investigating compounds from a series of protatranes as biostimulants for the growth of the Candida ethanolica yeast. The relevance of the study is associated with the need to determine conditions accelerating the growth of microorganisms in the presence of such highly effective, physiologically active and non-toxic compounds as protatranes. The research object was the Candida ethanolica yeast cultivated on a synthetic nutrient medium containing 1.5% ethanol solution as a carbon source. Protatrans were used at concentrations of 1·10-6 – 1·10-8 wt%. The number of yeast cells was controlled by determining the optical density of yeast suspensions using a KFK-3 Zomax photoelectrocolorimeter at a wavelength of 540 nm and optical path length of 10 mm. The determination of yeast biomass was carried out gravimetrically. The first stage of the work set out to study the accumulation of cells and biomass at various initial yeast cell concentrations. It was revealed that a slight increase in the initial concentration of yeast cells leads to a noticeable shift of the entire S-curve to the left. A comparison of the obtained data sets showed that the investigated protatranes significantly increase the specific growth rate and reduce the generation time during the log phase, provided that this phase accounts for a significant part of the cultivation process. However, the presence of protatranes significantly reduce the specific growth rate and increase the generation period in the log phase, provided that the culture remains in the stationary phase for a significant part of the cultivation time. This is likely to be associated with the positive effect of protatranes on protein synthesis, which is most intense during the log phase. The use of protatranes facilitates the control over the number of cells, amount of biomass, specific growth rate and generation time of the Candida ethanolica yeast depending on the initial cell concentration and, accordingly, the growth phase of the culture.

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New atranes and similar ionic complexes. Synthesis, structure, properties

Cited by 36 publications

References 89 publications

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Mechanism of Reactions of 1-Substituted Silatranes and Germatranes, 2,2-Disubstituted Silocanes and Germocanes, 1,1,1-Trisubstituted Hyposilatranes and Hypogermatranes with Alcohols (Methanol, Ethanol): DFT Study

Protatrans as biomodulators of <i>Candida ethanolica</i> growth

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