Synthesis and antioxidant activity of derivatives of 8Н -[1,2,4]triazolo[4,3-в][1,2,4]triazin-7-ones

Oxidative stress is usually connected with many severe diseases, such as atherosclerosis, hypertension, Alzheimer’s disease etc. Therefore, the search for new antioxidants is a very important pharmacological task. The aim of the study – to synthesize new derivatives of 8-(41-hydroxy-3R-benzylidenamino)-6-tertbutyl-8Н-[1,2,4]triazolo[4,3-b][1,2,4]triazine-7-ones and to evaluate their antioxidant properties in screening test in vitro as compared with ionol and ascorbic acid. By interaction of equimolar amounts of 8-amino-6-tert-butyl-8H-[1,2,4]triazolo[4,3-b][1,2,4]triazin7-one with the corresponding aromatic and heterocyclic aldehydes in ethanol, a series of Schiff bases with the key fragment 8H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one were synthesized. The structure and purity of all the substances obtained were confirmed by 1H NMR spectroscopy. Screening of compound’s antioxidant activity (AOA) was studied in vitro by their ability to inhibit lipoperoxide formation, induced by FeSO4 in yolk lipoproteins emulsion. It is shown, that, depending on the structure, the test substances exhibit both antioxidant and prooxidant properties. The regularities of the chemical structure – pharmacological action are established. It is shown that the introduction of electron-withdrawing substituents (F, Cl, Br and COOMe) into the benzene ring leads to a decrease in the antioxidant properties as to the base molecule 6-tert-butyl-8(benzylideneamino)-8Н-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-оne 8 а without substitutes. The most active were derivatives of 8-(benzylideneamino)-6-~{tert}-butyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin7-ones, which had a hydroxyl group and an additional oxyalkyl fragment in the third position of the benzene ring (8 l, 8 o). The data obtained substantiate the feasibility of further studying the most active derivatives of 6-tertbutyl-8-(benzylideneamino)-8Н-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-оnes as potential antioxidant agents.

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A Study on Synthesis and Antioxidant Activity Comparison of Novel Stilbenebenzamide Compounds

Medicinal Chemistry ◽

10.2174/1573406415666191114123004 ◽

2019 ◽

Vol 15 ◽

Author(s):

Aleksandra Kładna ◽

Paweł Berczyński ◽

Oya Bozdağ Dündar ◽

Irena Kruk ◽

Beyza Torun ◽

...

Keyword(s):

Antioxidant Activity ◽

Ascorbic Acid ◽

Antioxidant Activities ◽

Wide Spectrum ◽

Antioxidant Properties ◽

Butylated Hydroxytoluene ◽

Hydroxyl Group ◽

Antioxidant Power ◽

Total Antioxidant

Background: Stilbene phytalexis (1,2-diphenyloethylen) and benzamide are beneficial for human health. To increase the stilbene ring activity, a new series of its derivatives containing benzamide structure was synthesized and evaluated for their in vitro antioxidant power. Methods: 1H nuclear magnetic resonance, mass spectroscopy, and chromatographic analyses were used to confirm the successful synthesis. The antioxidant properties were determined by the elimination of , HO , DPPH , ABTS+ radicals, total antioxidant status (TAS) and the ferric reducing antioxidant activities (TAC) measurements. Results: Stilbenebenzamide compounds showed a wide spectrum of antioxidant ability, however their total antioxidant power was weaker than those of butylated hydroxytoluene (BHT), ascorbic acid, and resveratrol. The highest antiradical activity towards and HO was shown by the compounds with structures containing amine group (SBEBA, SBA) ( : 37.7 – 38.0% and 40.8 – 43.5%, HO : 29.8%, 28.7% inhibition, respectively) at1.25 mM concentration. The antiradical power of SBEBA (0.29) in DPPH assay was lower than those of resveratrol (1.83), ascorbic acid (3.63) and BHT (4.09). The TAS values of the synthesized compounds ranged from 152.9±5.3 to 240.2±6.7µM trolox equivalent/gram (TE/g) and were much lower than those of BHT (1304±43.0), reservatrol (1360±29.0) and ascorbic acid (2782±39.7) µM TE/g. Similarly, the TAC values ranging from 29.7±0.9 to 41.5±1.6 µM TE were weaker than that of resveratrol (239.2 ±6.7 µM TE/g). Conclusion: The results suggest that the presence of hydroxyl group in stilbene ring should be considered in further design of stilbenebenzamide compounds to enhance their antioxidant activity.

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Synthesis and antioxidant properties of some new 5-phenethyl-3-thio-1,2,4-triazoles

Pharmacia ◽

10.3897/pharmacia.68.e53320 ◽

2021 ◽

Vol 68 (1) ◽

pp. 129-133

Author(s):

Tetiana Ihnatova ◽

Andriy Kaplaushenko ◽

Yuliia Frolova ◽

Evheniy Pryhlo

Keyword(s):

Antioxidant Activity ◽

Antioxidant Properties ◽

Derivatives Of

Novel derivatives of 4-R-5-phenethyl-4H-1,2,4-triazole-3-thiols were synthesized. The proposed approaches and developed synthetic protocols provided the possibility to design 4-R-5-phenethyl-4H-1,2,4-triazole-3-thiols and their derivatives have been shown. The antioxidant activity of the synthesized compounds was evaluated in vitro by the method of the non-enzymatic initiation of BOD with salts of iron (II). When compared with existing antioxidants, some of our compounds were found to be more potent.

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Synthesis of some novel 3- (4-ethoxyphenyl) -5- (4-substituted) -4,5-dihydro-1H-pyrazole derivatives as potent antioxidant agents

International Journal of Research in Pharmaceutical Sciences ◽

10.26452/ijrps.v11i2.2035 ◽

2020 ◽

Vol 11 (2) ◽

pp. 1571-1577

Author(s):

Lakshminarayanan B ◽

Kannappan N ◽

Subburaju T ◽

Kalaichelvan V K

Keyword(s):

Hydrogen Peroxide ◽

Antioxidant Activity ◽

Ascorbic Acid ◽

Free Radical ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Assay Method ◽

Antioxidant Agents ◽

Ic50 Value

Pyrazolines are the most useful heterocyclic moiety in Pharmaceutical and Chemical fields and as the most potential molecules for the design of new chemical entities. Nitrogen-containing heterocyclic compounds, pyrazolines and their derivatives showed a variety of pharmacological activities, including antioxidant properties. In the present study, eleven novel ethoxylated pyrazoline derivatives were synthesized by condensing chalcones with electron releasingethoxy group at one end and different electron-donating, electron-withdrawing groups in another end with hydrazine hydrate andalcohol. The compounds synthesized were structural elucidated by their spectroscopic studies. All the compounds synthesized were evaluated for their in vitro antioxidant potential by 2,2’-diphenyl-1-picrylhydrazyl (DPPH)and hydrogen peroxide free radical scavenging assay methods.Some of these molecules possess moderate to good antioxidant activitywhen compared to standard ascorbic acid. The compound with methoxy group (EH2) exhibits potent antioxidant activity with IC50 value of 9.02 and 9.44µg/ml in DPPH and hydrogen peroxide assay method respectively and the compound with hydroxy group (EH9) also showed potent antioxidant activity with IC50 value of 12.41 and 14.56µg/ml in DPPH and hydrogen peroxide free radical scavengingassay method respectively when compared to standard. The compounds containing electron-donating substituents were found to be good antioxidantswhen compared to standard ascorbic acid.

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Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

Applied Sciences ◽

10.3390/app112411642 ◽

2021 ◽

Vol 11 (24) ◽

pp. 11642

Author(s):

Hatem A. Abuelizz ◽

Hanan A. A. Taie ◽

Ahmed H. Bakheit ◽

Mohamed Marzouk ◽

Mohamed M. Abdellatif ◽

...

Keyword(s):

Antioxidant Activity ◽

Electron Transfer ◽

Benzoic Acid ◽

Antioxidant Properties ◽

Biological Evaluation ◽

Hydrogen Atom Transfer ◽

Scavenging Activity ◽

Antioxidant Agents ◽

Power Capability

Fourteen triazole benzoic acid hybrids were previously characterized. This work aimed to screen their in vitro antioxidant activity using different assays, i.e., DPPH (1,1-diphenyl-1-picrylhydrazyl), reducing the power capability, FRAP (ferric reducing antioxidants power) and ABTS (2,2′-azino-bis(3-ethylben zothiazoline-6-sulfonate) radical scavenging. The 14 compounds showed antioxidant properties in relation to standard BHA (butylated hydroxylanisole) and Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid). Higher antioxidant activity was observed by the parent (1) at a concentration of 100 µg/mL (89.95 ± 0.34 and 88.59 ± 0.13%) when tested by DPPH and ABTS methods in relation to BHA at 100 µg/mL (95.02 ± 0.74 and 96.18 ± 0.33%). The parent (2) demonstrated remarkable scavenging activity when tested by ABTS (62.00 ± 0.24%), however, 3 was less active (29.98 ± 0.13%). Compounds 5, 6, 9, and 11 exhibited good scavenging activity compared to 1. DFT studies were performed using the B3LYP/6-311++g (2d,2p) level of theory to evaluate different antioxidant descriptors for the targets. Three antioxidant mechanisms, i.e., hydrogen atom transfer (HAT), sequential electron transfer proton transfer (SETPT) and sequential proton loss electron transfer (SPLET) were suggested to describe the antioxidant properties of 1–14. Out of the 14 triazole benzoic acid hybrids, 5, 9, 6, and 11 showed some good theoretical results, which were in agreement with some experimental outcomes. Based on the computed (PA and ETE) and (BDE and IP) values in (SPLET) and (HAT and SETPT) mechanisms, respectively, compound 9 emerged has having good antioxidant activity.

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Phenolic Profile and Antioxidant Activity of Ethanolic Extract of Larrea cuneifolia Cav. Leaves

Proceedings ◽

10.3390/foods_2020-07645 ◽

2020 ◽

Vol 70 (1) ◽

pp. 37

Author(s):

Maria Emilia Lorenzo ◽

Patricia Elizabeth Gómez ◽

Eugenia Sabatino ◽

Adrián Federico Segovia ◽

Lara Carolina Figueroa ◽

...

Keyword(s):

Antioxidant Activity ◽

Phenolic Compounds ◽

Antioxidant Properties ◽

Ethanolic Extract ◽

Central Valley ◽

Cell Types ◽

Phenolic Profile ◽

Antioxidant Characteristics ◽

Derivatives Of

The genus of the Zygophyllaceae family includes evergreen shrub species. Background highlights the antioxidant and anti-tumor activity of Larrea divaricate and nordihydroguayaretic acid (NDGA) due to their potential as a dietary supplement and food preservative, but little is known about Larrea cuneifolia. The aim of this work was to determine the antioxidant characteristics of ethanolic extracts of L. cuneifolia leaves collected in the central valley of Catamarca (Argentina). Total polyphenols content (TP) was determined by Folin-Ciocâlteu and the phenolic profile by HPLC-PDA-QTOF. The antioxidant activity was measured by in vitro (FRAP, TEAC and DPPH) and cellular (HepG2 and Caco2 cells) assays. The phenolic compounds identified were mainly derivatives of NDGA and flavonols derivatives of quercetin, kaempferol, isorhamnetin and gossypetin. TP content and antioxidant activity exceeded the values reported for L. divaricata. With regard to cytotoxicity, an increase in this parameter could be observed with the increase in the concentration of polyphenols in both cell types. Furthermore, in cells exposed to H2O2, a significant decrease in reactive oxygen species (ROS) concentration was observed for HepG2 cells. This effect can be used to study compounds with bioactivity on tumor cells. L. cuneifolia is a species rich in phenolic compounds, with antioxidant properties, and is a potential source of bioactive compounds for the production of functional foods.

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Synthesis and antioxidant activity of new selenium-containing quinolines

Medicinal Chemistry ◽

10.2174/1573406416666200403081831 ◽

2020 ◽

Vol 16 ◽

Cited By ~ 1

Author(s):

Benedetta Bocchini ◽

Bruna Goldani ◽

Fernanda S.S. Sousa ◽

Paloma T. Birmann ◽

Cesar A. Brüning ◽

...

Keyword(s):

Antioxidant Activity ◽

Superoxide Dismutase ◽

Radical Scavenging ◽

Building Blocks ◽

Antioxidant Potential ◽

In Vitro Assays ◽

Pharmacological Activities ◽

Antioxidant Power ◽

Antioxidant Agents

Background: Quinoline derivatives have been attracted much attention in drug discovery and synthetic derivatives of these scaffolds present a range of pharmacological activities. Therefore, organoselenium compounds are valuable scaffolds in organic synthesis because their pharmacological activities and their use as versatile building blocks for regio-, chemio-and stereoselective reactions. Thus, the synthesis of selenium-containing quinolines has great significance, and their applicability range from simple antioxidant agents, to selective DNA-binding and photocleaving agents. Objective: In the present study we describe the synthesis and antioxidant activity in vitro of new 7-chloroN(arylselanyl)quinolin-4-amines 5 by the reaction of 4,7-dichloroquinoline 4 with (arylselanyl)-amines 3. Methods: For the synthesis of 7-chloro-N(arylselanyl)quinolin-4-amines 5, we performed the reaction of (arylselanyl)- amines 3 with 4,7-dichloroquinoline 4 in the presence of Et3N at 120 °C in a sealed tube. The antioxidant activities of the compounds 5 were evaluated by the following in vitro assays: 2,2- diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, 2,2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric ion reducing antioxidant power (FRAP), nitric oxide (NO) scavenging and superoxide dismutase-like activity (SOD-Like). Results: 7-Chloro-N(arylselanyl)quinolin-4-amines 5a-d has been synthesized in yields ranging from 68% to 82% by the reaction of 4,7-dichloroquinoline 4 with arylselanyl-amines 3a-d using Et3N as base, at 120 °C, in a sealed tube for 24 hours and tolerates different substituents, such as -OMe and -Cl, in the arylselanyl moiety. The obtained compounds 5a-d presented significant results with respect to the antioxidant potential, which had effect in the tests of inhibition of radical’s DPPH, ABTS+ and NO, as well as in the test that evaluates the capacity (FRAP) and in the superoxide dismutase-like activity assay (SOD-Like). It is worth mentioning that 7-chloro-N(arylselanyl)quinolin-4-amine 5b presented excellent results, demonstrating a better antioxidant capacity when compared to the others. Conclusion: According to the obtained results 7-chloro-N(arylselanyl)quinolin-4-amines 5 were synthesized in good yields by the reaction of 4,7-dichloroquinoline with arylselanyl-amines and tolerates different substituents in the arylselanyl moiety. The tested compounds presented significant antioxidant potential in the tests of inhibition of DPPH, ABTS+ and NO radicals, as well as in the FRAP and superoxide dismutase-like activity assays (SOD-Like).

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Synthesis, Cytotoxicity and Antioxidant Activity of New Analogs of RC-121 Synthetic Derivatives of Somatostatin

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520618666180417164344 ◽

2019 ◽

Vol 18 (10) ◽

pp. 1417-1424 ◽

Cited By ~ 2

Author(s):

Emilia Naydenova ◽

Diana Wesselinova ◽

Svetlana Staykova ◽

Ivan Goshev ◽

Ljubomir Vezenkov

Keyword(s):

Antioxidant Activity ◽

Antioxidant Capacity ◽

Cell Line ◽

Cancer Cell ◽

Cancer Cell Line ◽

Colorectal Cancer Cell Line ◽

Cervical Cancer Cell Line ◽

Synthetic Derivatives ◽

Derivatives Of

Background: Based on the structure of RC-121 (D-Phe-c (Cys-Tyr-D-Trp-Lys-Val-Cys)-Thr-NH2, - synthetic derivatives of somatostatin), some analogs were synthesized and tested for in vitro cytotoxic and antioxidant activity. Objectives: The new analogs were modifyed at position 5 with Dap (diaminopropanoic acid), Dab (diaminobutanoic acid) and Orn and at position 6 with the unnatural amino acids Tle (t-leucine). Methods: The in vitro cytotoxic effects of the substances were investigated against a panel of human tumor cell lines HT-29 (Human Colorectal Cancer Cell Line), MDA-MB-23 (Human Breast Cancer Cell Line), Hep G-2 (Human Hepatocellular Carcinoma Cell Line) and HeLa (cervical cancer cell line). The antioxidant capacities were tested by ORAC (Oxygen Radical Antioxidant Capacity) and HORAC (Hydroxyl Radical Averting Capacity) methods. Results: All substances expressed significantly higher antioxidant capacity by comparison with galic acid and Trolox. All substances showed considerable antioxidant capacity as well. Compound 2T (D-Phe-c(Cys-Tyr-DTrp- Dap-Tle-Cys)-Thr-NH2)had the highest antioxidant effect. The compound 4T (D-Phe-c(Cys-Tyr-D-Trp- Orn-Tle-Cys)-Thr-NH2) displayed antiproliferative effect on HeLa cells with IC50 30 µM. The peptide analog 3T (D-Phe-c(Cys-Tyr-D-Trp-Lys-Tle-Cys)-Thr-NH2) exerted the most pronounced inhibition on the cell vitality up to 53%, 56% and 65% resp. against MDA-MB-23, Hep G-2, HeLa in the higher tested concentration. Conclusion: The somatostatin analogs showed moderate influence on the vitality of different tumor cells and could be used in changing their pathology.

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Chemical Composition, In Vitro and In Silico Antioxidant Potential of Melissa officinalis subsp. officinalis Essential Oil

Antioxidants ◽

10.3390/antiox10071081 ◽

2021 ◽

Vol 10 (7) ◽

pp. 1081

Author(s):

Matilda Rădulescu ◽

Călin Jianu ◽

Alexandra Teodora Lukinich-Gruia ◽

Marius Mioc ◽

Alexandra Mioc ◽

...

Keyword(s):

Antioxidant Activity ◽

Chemical Composition ◽

Essential Oil ◽

In Silico ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Inhibitory Effect ◽

Melissa Officinalis ◽

Β Carotene

The investigation aimed to study the in vitro and in silico antioxidant properties of Melissa officinalis subsp. officinalis essential oil (MOEO). The chemical composition of MOEO was determined using GC–MS analysis. Among 36 compounds identified in MOEO, the main were beta-cubebene (27.66%), beta-caryophyllene (27.41%), alpha-cadinene (4.72%), caryophyllene oxide (4.09%), and alpha-cadinol (4.07%), respectively. In vitro antioxidant properties of MOEO have been studied in 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging, and inhibition of β-carotene bleaching assays. The half-maximal inhibitory concentration (IC50) for the radical scavenging abilities of ABTS and DPPH were 1.225 ± 0.011 μg/mL and 14.015 ± 0.027 μg/mL, respectively, demonstrating good antioxidant activity. Moreover, MOEO exhibited a strong inhibitory effect (94.031 ± 0.082%) in the β-carotene bleaching assay by neutralizing hydroperoxides, responsible for the oxidation of highly unsaturated β-carotene. Furthermore, molecular docking showed that the MOEO components could exert an in vitro antioxidant activity through xanthine oxidoreductase inhibition. The most active structures are minor MOEO components (approximately 6%), among which the highest affinity for the target protein belongs to carvacrol.

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Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

Molecules ◽

10.3390/molecules26123579 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3579

Author(s):

Svetlana A. Popova ◽

Evgenia V. Pavlova ◽

Oksana G. Shevchenko ◽

Irina Yu. Chukicheva ◽

Aleksandr V. Kutchin

Keyword(s):

Antioxidant Activity ◽

Antioxidant Properties ◽

Biological Properties ◽

High Reactivity ◽

Biologically Active ◽

Brain Lipids ◽

Wide Range ◽

Privileged Structure ◽

Vitro Model

The pyrazoline ring is defined as a “privileged structure” in medicinal chemistry. A variety of pharmacological properties of pyrazolines is associated with the nature and position of various substituents, which is especially evident in diarylpyrazolines. Compounds with a chalcone fragment show a wide range of biological properties as well as high reactivity which is primarily due to the presence of an α, β-unsaturated carbonyl system. At the same time, bicyclic monoterpenoids deserve special attention as a source of a key structural block or as one of the pharmacophore components of biologically active molecules. A series of new diarylpyrazoline derivatives based on isobornylchalcones with different substitutes (MeO, Hal, NO2, N(Me)2) was synthesized. Antioxidant properties of the obtained compounds were comparatively evaluated using in vitro model Fe2+/ascorbate-initiated lipid peroxidation in the substrate containing brain lipids of laboratory mice. It was demonstrated that the combination of the electron-donating group in the para-position of ring B and OH-group in the ring A in the structure of chalcone fragment provides significant antioxidant activity of synthesized diarylpyrazoline derivatives.

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Synthesis and antioxidant properties of 2-(3-(hydroxyimino)methyl)-1H-indol-1-yl)acetamide derivatives

Future Journal of Pharmaceutical Sciences ◽

10.1186/s43094-020-00090-6 ◽

2020 ◽

Vol 6 (1) ◽

Author(s):

Chandravadivelu Gopi ◽

Magharla Dasaratha Dhanaraju

Keyword(s):

Antioxidant Activity ◽

Condensation Reaction ◽

Antioxidant Properties ◽

Side Chain ◽

Antioxidant Power ◽

H Nmr ◽

Antioxidant Agents ◽

Phenyl Rings ◽

Ferric Reducing Antioxidant Power ◽

Ft Ir

Abstract Background The main aim of this work was to synthesise a novel N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1H-indol-1-yl) acetamide derivatives and evaluate their antioxidant activity. These compounds were prepared by a condensation reaction between 1H-indole carbaldehyde oxime and 2-chloro acetamide derivatives. The newly synthesised compound structures were characterised by FT-IR, 1H-NMR, mass spectroscopy and elemental analysis. Furthermore, the above-mentioned compounds were screened for antioxidant activity by using ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) methods. Result The antioxidant activity result reveals that most of the compounds were exhibiting considerable activity in both methods and the values are very closer to the standards. Among the synthesised compounds, compound 3j, 3a and 3k were shown remarkable activity at low concentration. Conclusion Compounds 3j, 3a and 3k were shown highest activity among the prepared analogues due to the attachment of halogens connected at the appropriate place in the phenyl ring. Hence, these substituted phenyl rings considered as a perfect side chain for the indole nucleus for the development of the new antioxidant agents.

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