Synthesis, structure, and antioxidant activity of hybrid N-substituted salicylic acid amides

Сторожок, Н. М.; Medyanik, N. P.; Krysin, A. P.; Krekov, S. A.; Борисенко, В. Е.

doi:10.1134/s1070428013070129

Cited by 5 publications

(5 citation statements)

References 2 publications

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“…It is known that amides and secondary amines are weaker proton donors in hydrogen bonding than hydroxyl-containing compounds. The v(NH) band is shifted over the band of the monomer from 14 to 74 cm À 1 upon the formation of a complex of the N-H…O=C-type [10]. It is seen from Figure 1 that no substantial shift of the v(NH) bands is observed in the spectral of the studied compounds.…”

Section: Results and Discussion Of Ir Spectra Of Native Compounds Formentioning

confidence: 88%

“…Oxygen was removed from solutions by argon bubbling. The kinetics of oxidation of methyloleate (0.67 mol L À1 ) in the presence of amides of salicylic acid was studied in modified Warburg-type installations, fixing the amount of absorbed oxygen along the course of the reaction [4,10]. As inert to the oxidation of the solvent, chlorobenzene purified by the simple distillation method was used.…”

Section: Methodsmentioning

confidence: 99%

“…As inert to the oxidation of the solvent, chlorobenzene purified by the simple distillation method was used. The temperature of the experiments is (60 AE 0.2) C [3,10]. From the kinetic curves, the period of induction (τ) was determined as a segment on the time scale, cut off by a perpendicular dropped from the point of intersection of the tangents.…”

Section: Methodsmentioning

confidence: 99%

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Kinetics and Mechanism of Photoconversion of N-Substituted Amides of Salicylic Acid

Сторожок¹,

Medyanik²

2018

Photochemistry and Photophysics - Fundamentals to Applications

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Studied using optical spectroscopy, stationary, and nanosecond laser photolysis (Nd:YAG laser 355 nm) conversion products in heptane of N-substituted amides of salicylic acid: N-(4hydroxyhydro-3,5-di-tert-butylphenyl) amide 2-hydroxy-3-t-butyl-5-ethylbenzoic acid (1), 2-(4-hydroxy-3,5-hydroxybenzoic acid)-di-tert-butylphenyl) propyl] amide (2), N-(4hydroxyphenyl) amide 2-hidroxy benzoic acid (3), and 2-hydroxy-3-t-butyl-5-ethylbenzoic acid N-[3-(4-hydroxy-3,5-di-t-butylphenyl) propyl] amide (4). It is shown that amides exist both in the unbound state and in complexes with intra-and intermolecular hydrogen bonding. Free phenolic groups of amides undergo photolysis, which leads to the formation of a triplet state and phenoxyl radicals RO•, presumably due to the absorption of the second photon by the excited singlet state. Triplet-triplet annihilation and recombination (kr ≈ 2.3Á10 8 Lmo l À1 s) are the main channels for the decay of the triplet state and radicals RO•. UV irradiation of the compounds leads to the excitation of amide groups, and radical products are not formed due to ionization of the NH bond. The process of initiated UV oxidation of the model substrate (methyloleate) in the presence of amides 1-4 was compared with the known antioxidants (AO): dibunol (2,6-di-tert-butyl-4-methylphenol) (5) and αtocopherol (6-hydroxy-2,5,7,8-tetramethyl-2-phytyl chromane) (6). It has been shown that all amides of salicylic acid (I-IV) effectively inhibit the oxidation of methyl oleate, initiated by UV irradiation. The mechanism of the inhibitory effect of compounds has been established, which is associated with the possibility of direct interaction of phenols with free radicals (antiradical activity). Testing of antiradical activity of amides (I-IV), estimated by the method of chemiluminescence, made it possible to determine the range of reaction rate constants with peroxyl radicals RO • 2 k 7 =(0. 5 2-6.86) • 10 4 mL À1 s À1. The interrelation of antioxidant properties of amides of salicylic acid (I-IV) and features of their structure is established. It was shown that the introduction of o-tert-butyl substituents and the separation of aromatic fragments by three methylene groups lead to a significant increase in antioxidant activity.

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Section: Results and Discussion Of Ir Spectra Of Native Compounds Formentioning

confidence: 88%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Kinetics and Mechanism of Photoconversion of N-Substituted Amides of Salicylic Acid

Сторожок¹,

Medyanik²

2018

Photochemistry and Photophysics - Fundamentals to Applications

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“…11 Fatty amide derivatives of SA also show a high affinity for stratum corneum and present safer topical application since they do not metabolize and enter into systemic circulation, accumulating in the uppermost layer of skin. 12,13 Lipophilic hydroxy acid derivatives of SA reduced the number of non-inammatory lesions of comedonal acne by up to 55.6% as compared to salicylic acid, which reduced it by 48.5%; 14 SA amides also present antioxidant activity and HIV-1 integrase inhibition, 15,16 same as observed with 3-keto SA chalcones, exhibiting HIV-1 integrase inhibition. 17 Therefore, SA and its analogues (amides, esters, fatty amides, and fatty acid) present a large number of biological activities and have been largely studied in academic, medicinal, and pharmaceutical areas.…”

Section: Introductionmentioning

confidence: 89%

Fast synthesis of amides from ethyl salicylate under microwave radiation in a solvent-free system

et al. 2017

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“…On the other hand, carboxamide derivatives exhibited a vital importance in medicinal applications. Thus, literature is full of examples for bioactive carboxamides especially as antioxidant agents . Many palmitic acid amides were described as potent anti‐inflammatory and antioxidant agents .…”

Section: Introductionmentioning

confidence: 99%

Substituted quinolinones. 31. Some new pyrano[3,2‐c]quinoline‐3‐carboxamides and their antioxidant activity

Othman

Hassan

Abass

2019

Journal of Heterocyclic Chem

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1‐Ethyl‐4‐hydroxy‐2‐oxo‐1,2‐dihydroquinoline‐3‐carbaldehyde (1) was annulated using malonic acid and/or its ethyl ester to furnish pyrano[3,2‐c]quinoline‐3‐carboxylic acid 2 and its ester 3. Interconversions between acid 2 and ester 3 were successfully carried out. The anticipated pyrano[3,2‐c]quinoline‐3‐carboxamides 5–12 were conveniently attained via condensation of ester 3 with the proper amine. Surprisingly, treatment of ester 3 with dimethylformamide (DMF) in acidic media led to the carboxamide 5. All attempts to convert ester 3 to its corresponding acid hydrazides by interaction with the proper hydrazine derivative led to formation of pyrazolidinediones 15 and 17. Ester 3 underwent cyclo‐condensation with malononitrile dimer affording pyrido[3′,4′:5,6]pyrano[3,2‐c]quinoline derivative 18. The new compounds revealed significant antioxidant effect, which suggests that most of them are possible potent antioxidant agents.

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Synthesis, structure, and antioxidant activity of hybrid N-substituted salicylic acid amides

Cited by 5 publications

References 2 publications

Kinetics and Mechanism of Photoconversion of N-Substituted Amides of Salicylic Acid

Kinetics and Mechanism of Photoconversion of N-Substituted Amides of Salicylic Acid

Fast synthesis of amides from ethyl salicylate under microwave radiation in a solvent-free system

Substituted quinolinones. 31. Some new pyrano[3,2‐c]quinoline‐3‐carboxamides and their antioxidant activity

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