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Шадыро, О. И.; Сорокин, В. Л.; Ксендзова, Г. А.; Полозов, Г. И.; Николаева, С. Н.; Pavlova, N. I.; Savinova, Olga V.; Бореко, Е. И.

doi:10.1023/a:1027395627461

Cited by 14 publications

(20 citation statements)

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“…1 (curves 6, 7), the spectra are shown for solutions of O-methylated derivatives of aminophenols in n-hexane. Compound AP IV is obtained by methylation of AP III using dimethylsulfate [7]. As a consequence of the reaction, in the spectrum of AP IV (curve 6) we observe a band for NH vibrations with ν max = 3425 cm -1 , while the vibration band for OH vibrations is missing in the spectrum since there are no OH groups in this compound.…”

Section: Thus the Absence Of Absorption In The Region Of Vibrations Omentioning

confidence: 98%

“…The high efficacy of phenols has been established for prophylaxis and treatment of pathological conditions due to breakdowns in the antioxidant system of the body [4]. Today, derivatives of aminophenols are widely used as antiviral drugs for treatment of herpes infection [5][6][7]. Furthermore, some derivatives of diphenols [8,9] and aminophenols [10,11] have proven to be effective regulators of radiationinduced reactions involving participation of different types of organic radicals.…”

Section: Introductionmentioning

confidence: 99%

“…The Experiment. The compounds AP I to AP IV and AP VI (see Table 1) were synthesized by the procedures in [7,[14][15][16][17]; AP V and AP VII were synthesized by familiar methylation procedures [18,19]. The reliability of the chemical structure of the synthesized aminophenol derivatives was confirmed by NMR and mass spectrometry experimental data.…”

Section: Introductionmentioning

confidence: 99%

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Intramolecular hydrogen bonds and antioxidant activity of aminophenols

et al. 2007

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We have used IR Fourier spectroscopy to study intramolecular interactions in solutions of aminophenols in nhexane. When the hydroxyl group in the molecule is ortho to the amino group, O-H⋅⋅⋅N and N-H⋅⋅⋅O intramolecular hydrogen bonds are formed in the aminophenols. Adding two tert-butyl groups to the benzene ring of ortho-aminophenols strengthens the O-H⋅⋅⋅N bond in the molecules, and prevents formation of an N-H⋅⋅⋅O bond. Additional acylation of the amino group in ortho-aminophenols leads to formation of an O-H⋅⋅⋅O=C intramolecular hydrogen bond. Formation of the above-indicated intramolecular hydrogen bonds in aminophenols affects the course of radiation-induced reactions occurring in n-hexane with participation of these compounds. The antioxidant properties of the aminophenols are enhanced when the hydroxyl groups in the molecules are found in the free state, and are diminished when strong O-H⋅⋅⋅N or O-H⋅⋅⋅O=C intramolecular hydrogen bonds are formed.

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Section: Thus the Absence Of Absorption In The Region Of Vibrations Omentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Intramolecular hydrogen bonds and antioxidant activity of aminophenols

et al. 2007

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“…Certain derivatives of 4,6-di-(tert-butyl)-2-aminophenol (AP) have also exhibited high antiviral activity against Herpes Simplex and flu viruses [3][4][5][6][7][8]. The pharmacological properties of AP may also be due to their ability to affect the course of free-radical reactions in biological systems.…”

Section: Introductionmentioning

confidence: 99%

“…According to the literature [5,7,8], AP I, AP III, AP IV, AP V, and AP VI exhibited in experiments in cell cultures activity against Herpes Simplex virus whereas AP II and AP VII were practically inactive. Data on the antiviral activity of AP VIII have not yet been published.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular interactions of N-(3,5-di-tert-butyl-2-hydroxyphenyl)acetamide derivatives

et al. 2010

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Manifestation of intramolecular and intermolecular interactions in infrared absorption spectra of biologically active aminophenols

et al. 2008

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529.1.047;543.42 FTIR methods were used to study intramolecular and intermolecular interactions in solutions and the solid state of the biologically active aminophenols 2-anilino-4,6-di-tert-butylphenol, N-(3,5-di-tert-butyl-2-methoxyphenyl)aniline, and 2,4-di-tert-butyl-10H-1-phenothiazinol. An analysis of the IR spectra has shown that intramolecular interactions between the OH and NH groups occur in solutions of aniline in CCl 4 are present in the non-associated state because of the absence of hydroxyl groups in the molecular structure. The OH and NH groups in solutions of 2,4-di-tert-butyl-10H-1-phenothiazinol in CCl 4 do not interact within the molecule due to a decrease in the conformational mobility of the molecular fragments due to the presence of the rigid C Ar -S-C Ar molecular bond in this compound. Intermolecular interactions involving the NH groups occur in the solid state of these compounds. Introduction. Derivatives of phenols and aromatic amines are widely used as stabilizers of industrial organic materials and preservatives of food products [1, 2]. Certain derivatives of diphenols [3, 4] and aminophenols [5, 6] have turned out to be effective regulators of radiation-induced reactions involving various types of organic radicals. It has been demonstrated [7] that the antioxidant properties of aminophenol (AP) derivatives are enhanced when the hydroxyls in the molecules are free and diminished when intramolecular H-bonds (IHB) of the O-H⋅⋅⋅N or O-H⋅⋅⋅O=C are formed.The aforementioned compounds have also been found to be highly effective in the treatment and cure of pathologies caused by disruptions in the antioxidant system of an organism [8]. AP derivatives are also currently used as antiviral agents to treat herpes infections [9][10][11].Thus, a multifaceted study of these compounds, which have a broad spectrum of functional properties, is interesting to chemistry, pharmacology, and medicine.Herein we present results of an IR spectroscopic study of intramolecular and intermolecular interactions (IaMI and IrMI) of the three structurally similar and biologically different AP derivatives 2-anilino-4,6-di-tert-butylphenol (henceforth AP I), N-(3,5-di-tert-butyl-2-methoxyphenyl)aniline (AP II), and 2,4-di-tert-butyl-10H-1-phenothiazinol (AP III).

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Cited by 14 publications

References 0 publications

Intramolecular hydrogen bonds and antioxidant activity of aminophenols

Intramolecular hydrogen bonds and antioxidant activity of aminophenols

Intramolecular interactions of N-(3,5-di-tert-butyl-2-hydroxyphenyl)acetamide derivatives

Manifestation of intramolecular and intermolecular interactions in infrared absorption spectra of biologically active aminophenols

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