Synthesis and hepatoprotector activity of water-soluble derivatives of aminoalkylphenols

Dyubchenko, O. I.; Никулина, В. В.; Markov, A. F.; Кандалинцева, Н. В.; Просенко, А. Е.; Khoshchenko, O. M.; Shwarts, Ya. Sh.; Душкин, М. И.

doi:10.1007/s11094-006-0101-z

Cited by 7 publications

(8 citation statements)

References 5 publications

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“…11, 21 Alkylphthalimide 9b and propylamine 6b were synthesized according to a known procedure. 21 N,N Dimethyl 5 (3,5 di tert butyl 4 hydroxyphenyl)pentyl amine (1i).…”

Section: Resultsmentioning

confidence: 99%

“…11, 21 Alkylphthalimide 9b and propylamine 6b were synthesized according to a known procedure. 21 N,N Dimethyl 5 (3,5 di tert butyl 4 hydroxyphenyl)pentyl amine (1i). 1 Chloro 5 (3,5 di tert butyl 4 hydroxyphenyl)pen tane (2.3 g, 7.4 mmol), dimethylamine (2.0 g, 14.8 mmol), and potassium carbonate (2.1 g, 14.8 mmol) were placed in a 50 mL ampule, and ethanol (10 mL) was added.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and inhibitory activity of alkyl(hydroxyaryl)amines

et al. 2007

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The reaction of ω (4 hydroxyaryl)haloalkanes with various nitrogen containing agents afforded primary, secondary, and tertiary amino derivatives of 2,6 dialkylphenols. For the compounds synthesized, the reaction rate constants with peroxide radicals were measured for cumene and methyl oleate oxidation. The total inhibitory activity in the model reactions of thermal autooxidation of lard and hexadecane was studied. The rate constants of alkyl(hydr oxylaryl)amines are the same as those of the corresponding alkylphenols, whereas the total inhibitory activity of some alkyl(hydroxylaryl)amines exceeds substantially that for alkylphenols. Alkyl(hydroxyaryl)amines (aminoalkylphenols) are highly efficient inhibitors for free radical oxidation of vari ous organic substrates. According to patent data, 1-4 they can be used as stabilizers of polymeric materials, rubbers, lubricants, and diesel and jet fuels. In addition, alkyl(hydr oxyaryl)amines and their salts possess a high spectrum of biological activity, in particular, they manifest antiphlo gistic, 5 antiarrhythmic, 6 radioprotective, and antitumor 7 properties. At the same time, regularities of changes in the antioxidation activity of alkyl(hydroxyaryl)amines de pending on their structure are insufficiently studied: these data are presented only in few studies 8-12 devoted pre dominantly to benzylic compounds.In the present study, we synthesized structurally re lated series of alkyl(hydroxyaryl)amines 1-6 and studied comparatively their antioxidation activity in various model systems. Results and DiscussionTertiary amines 1-3 were synthesized by the reac tions of the corresponding ω (4 hydroxyaryl)chloro alkanes 7 with dialkylamines in yields up to 90% (Scheme 1). Scheme 1 7: R = R´ = Bu t , n = 2 (a), 3 (b), 4 (c); R = Bu t , R´ = H, n = 3 (d); R = R´ = Me, n = 3 (e); R = R´ = H, n = 3 (f); R = R´ = cyclo C 6 H 11 , n = 3 (g); R = Bu t , R´ = Me, n = 3 (h); R = R´ = Bu t , n = 5 (i)Secondary amines 4a-c and 5a-c were synthesized similarly in 60-72% yields by the reactions of chloro alkanes 7 with methyl and propylamines.Primary amines 6а-с were synthesized from bromo alkanes 8а-с through intermediate alkylphthalimides 9а-с (Scheme 2). * Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth. R = R´ = Bu t , n = 2 (a), 3 (b), 4 (c); R = Bu t , R´ = H, n = 3 (d); R = R´ = Me, n = 3 (e); R = R´ = H, n = 3 (f); R = R´ = cyclo C 6 H 11 , n = 3 (g); R = Bu t , R´ = Me, n = 3 (h); R = R´ = Bu t , n = 5 (i) R″ = Me (1a-i, 4a-c), Et (2a-f), Pr (3a-d, 5a-c), H (6a-c)

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“…11, 21 Alkylphthalimide 9b and propylamine 6b were synthesized according to a known procedure. 21 N,N Dimethyl 5 (3,5 di tert butyl 4 hydroxyphenyl)pentyl amine (1i).…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis and inhibitory activity of alkyl(hydroxyaryl)amines

et al. 2007

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“…3-(Trimethylsilylethynyl)furocoumarin (14) [18], 2,4-dimethoxyphenylacetylene (3c) [33], 2,4-dihydroxyphenylacetylene (3d) [33], methyl 2-acetylamino-5-ethynylbenzoate (3e) [34], 4-(2-azidoethyl)phenol (15) [30], 4-(bromomethyl)-2,3,5,6-tetramethylphenol (25) [35,36], 4-(bromomethyl)-2,6-ditert-butylphenol (26) [37,38], 4-(2-bromoethyl)-2,6di-tert-butylphenol (27) [39], 4-(3-chloropropyl)-2,6-(di-tert-butyl)phenol (28) [40], and dichlorobis(tri-phenylphosphine)palladium(II) [41] were synthesized by known methods.…”

Section: Methodsmentioning

confidence: 99%

Plant coumarins: XV. Oreoselone in the synthesis of 3-[(Z)-alkenyl]- and 3-(1H-1,2,3-triazol-4-yl)psoralens

Lipeeva

Шульц

2015

Russ J Org Chem

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Sonogashira reaction of 2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen with terminal arylacetylenes gave 2-isopropyl-3-(arylethynyl)psoralens which were converted into the corresponding Z-alkenes by reduction with hydrogen in the presence of Lindlar catalyst or by thermal decomposition of preliminarily prepared Ti(II)-alkyne complexes. The reaction of 2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen with trimethylsilylacetylene afforded 2-isopropyl-3-[(trimethylsilyl)ethynyl]psoralen which reacted with 4-(ω-azidoalkyl)phenols in the presence of copper(I) bromide and triethylamine to produce 3-{1-[ω-(4-hydroxyaryl)alkyl]-1H-1,2,3-triazol-4-yl}-2-isopropylpsoralens.* For communication XIV, see [1].

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“…Mannich bases have applications the field medicinal chemistry, the product synthetic polymers, the petroleum industry, as products used in water treatment, cosmetics, the dyes industry, etc 1 . In addition, Mannich bases have biological activity such as anticancer 2,3 , antibacterial [4][5][6] , antimycobacterial [7][8][9] , anti inflammatory [10][11][12] , analgesic 13,14 , antifungal 15,16 , antitumor 17,18 namely the 1-aryl-2-dimethylaminomethyl-2-propen-1-one hydrochlorides 1a-e and 1-aryl-3-dimethylamino-2-hydroxymethyl-1-propanone hydrochlorides 2a-e. A number of these compounds possess marked cytotoxic potencies (IC(50, antiviral [19][20][21] , antidepressant 22,23 , antiulcer 24 , anticonvulsant 25 , antimalarial 26,27 and antioxidant activities 28 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and investigations of antimicrobial, antioxidant activities of novel di-[2-(3-alkyl/ aryl-4,5-dihydro-1h-1,2,4-triazol-5-one-4-yl)- azomethinephenyl] isophtalates and mannich base derivatives

Yüksek¹,

Özdemir²,

Manap³

et al. 2020

actapharm

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In this study, the synthesis of di-[2-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinephenyl] isophtalates (2a-g) from the reactions of 3-alkyl/ aryl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1a-g) with di-(2-formylphenyl) isophtalate is described. Then, the compounds 2 were treated with morpholine in the presence of formaldehyde to synthesize di-{2-[1-(morpholine-4-yl-methyl)-3alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-azomethinephenyl} isophtalates (3a-g). The newly synthesized compounds were characterized using IR, 1 H-NMR and 13 C-NMR spectral data. In addition, the compounds synthesized were screened for their antimicrobial activities. Furthermore, the antioxidant properties of the newly synthesized compounds were analysed for their in-vitro potential antioxidant activities in three different methods (reducing power, free radical scavenging and metal chelating activity). These antioxidant activities were compared to those from standard antioxidants, such as BHA, BHT, EDTA and α-tocopherol.

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Synthesis and hepatoprotector activity of water-soluble derivatives of aminoalkylphenols

Cited by 7 publications

References 5 publications

Synthesis and inhibitory activity of alkyl(hydroxyaryl)amines

Synthesis and inhibitory activity of alkyl(hydroxyaryl)amines

Plant coumarins: XV. Oreoselone in the synthesis of 3-[(Z)-alkenyl]- and 3-(1H-1,2,3-triazol-4-yl)psoralens

Synthesis and investigations of antimicrobial, antioxidant activities of novel di-[2-(3-alkyl/ aryl-4,5-dihydro-1h-1,2,4-triazol-5-one-4-yl)- azomethinephenyl] isophtalates and mannich base derivatives

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