scholarly journals Design and Antiproliferative and Antioxidant Activities of Furan-Based Thiosemicarbazides and 1,2,4-Triazoles: Their Structure-Activity Relationship and SwissADME Predictions

2021 ◽  
Author(s):  
Yusuf SICAK
Keyword(s):  
Antioxidant Activity ◽  
Physicochemical Properties ◽  
Antioxidant Activities ◽  
Cancer Cell Line ◽  
Clinical Use ◽  
Biological Applications ◽  
Triazole Derivatives ◽  
Structure Activity ◽  
Pharmacokinetic Properties ◽  
Drug Similarity

Abstract Due to the limited number of drugs in current clinical use, the diverse biological applications of furan have encouraged the preparation of a wide variety of thiosemicarbazide and triazole derivatives for the purpose of developing new drug agents. In this study aimed to investigate the antiproliferative and antioxidant activities of some thiosemicarbazides (1-12) and 1,2,4-triazoles (13-24). Compound 15 (IC50: 8.81±0.28 µM) showed the highest antiproliferative activity against the cervical (HeLa) cancer cell line among the compounds. Compounds 15, 20, 21, and 22 of the 1,2,4-triazole derivatives (13-24) exhibited excellent antioxidant activity. Moreover, the physicochemical properties, pharmacokinetic properties, drug similarity, and medicinal chemistry properties of all synthesized products were calculated using SwissADME. In addition, the effect of the structure–activity relationships of the 1,2,4-triazole derivatives (13-24) on the results of antiproliferative and antioxidant activity assays was evaluated.

scholarly journals CYTOTOXIC AND ANTIOXIDANT ACTIVITIES OF SECONDARY METABOLITES FROM PULICARIA UNDULATA

2016 ◽  
Vol 8 (9) ◽  
pp. 150 ◽  
Author(s):  
Taha A. Hussien ◽  
Sayed A. El-toumy ◽  
Hossam M. Hassan ◽  
Mona H. Hetta
Keyword(s):  
Antioxidant Activity ◽  
Secondary Metabolites ◽  
Antioxidant Activities ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Hep G2 ◽  
Structure Activity ◽  
Dpph Method ◽  
Mcf 7

<p><strong>Objective:</strong><strong> </strong>To evaluate the <em>in vitro</em> cytotoxicity, antioxidant activities and structure-activity relationship of secondary metabolites isolated from <em>Pulicaria undulata</em>.</p><p><strong>Methods: </strong>The methylene chloride-methanol (1:1) extract of the air-dried aerial parts of <em>Pulicaria undulata</em> was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of the isolated compounds were determined on the basis of the extensive spectroscopic analysis, including 1D and 2D NMR and compared with the literature data. The crude extract and the isolated compounds were evaluated for <em>in vitro</em> antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method and cytotoxic assay using human breast cancer (MCF-7) and hepatoma (Hep G2) cell line.</p><p><strong>Results: </strong>Nine secondary metabolites were isolated from <em>Pulicaria undulata</em> in this study. Of which two terpenoidal compounds; 8-epi-ivalbin and 11β, 13-dihydro-4H-xanthalongin 4-<em>O</em>-β-D-glucopyranoside firstly isolated from the genus <em>pulicaria</em> and three flavonoids; eupatolitin, 6-methoxykaempferol, and patulitrin firstly isolated from <em>P. undulata</em>. 6-methoxykaempferol (IC<sub>50</sub> 2.3 µg/ml) showed the most potent antioxidant activity. The highest cytotoxic effect against MCF-7 and Hep G2 cells was obtained with eupatolitin (IC<sub>50</sub> 27.6 and 23.5 µg/ml) respectively. The structure-activity relationship was also examined and the findings presented here showed that 3, 5, 7, 4' and 3, 5, 4', 5'-hydroxy flavonoids were potent antioxidant and has cytotoxic activity.</p><p><strong>Conclusion: </strong><em>Pulicaria undulata</em> is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as antioxidant drug and in the treatment of cancer.</p>

scholarly journals Synthesis of Novel and Potential Antimicrobial, Antioxidant and Anticancer Chalcones and Dihydropyrazoles Bearing Isoxazole Scaffold

Proceedings ◽  
2020 ◽  
Vol 41 (1) ◽  
pp. 16
Author(s):  
Afzal Shaik ◽  
Palleapati Kishor ◽  
Venkata Kancharlapalli
Keyword(s):  
Antioxidant Activities ◽  
Biological Activities ◽  
Cancer Cell Line ◽  
Prostate Cancer Cell Line ◽  
Antifungal Compound ◽  
Anticancer Activities ◽  
Anticancer Properties ◽  
Structure Activity ◽  
Normal Human Cell ◽  
Normal Human

A series of isoxazole based (E)-1-(isoxazole-5-yl)-3-(substituted phenyl)-prop-2-en-1-ones (chalcones, 3a-3o) and 3-(isoxazol-5-yl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide (dihydropyrazoles, 4a-4o) were synthesized, characterized and evaluated for their antimicrobial, antioxidant and anticancer properties. Chalcones exhibited excellent antibacterial and antioxidant activities whereas the dihydropyrazoles shown superior antifungal and anticancer activities. The compound 3l containing 3,4,5-trimethoxy phenyl ring showed the potent antibacterial activity (MIC = 1 µg/mL) as well as the antioxidant activity (IC50 = 5 µg/mL) whereas the dihydropyrazole, 4o (MIC = 0.5 µg/mL) bearing the 2-chloro-3,4-dimethoxyphenyl was the potent antifungal compound identified. The dihydropyrazoles 4n and 4h possessing 2-fluoro-3,4-dimethoxyphenyl and 3,4-dimethoxyphenyl substituents exhibited potent anticancer activity against prostate cancer cell line (DU-145) with MIC 2 and 4 µg/mL respectively. The structure activity relationships had shown that there is a marked influence of both electron withdrawing halogens and electron releasing methoxyl groups on the above biological activities. All the compounds were evaluated for toxicity on normal human cell lines (LO2) and found to be non-toxic. These studies could help to synthesize, explore and identify new isoxazole containing leads for antimicrobial, antioxidant and anticancer properties.

scholarly journals Antioxidant and Chemosensitizing Effects of Flavonoids with Hydroxy and/or Methoxy Groups and Structure-Activity Relationship

2007 ◽  
Vol 10 (4) ◽  
pp. 537 ◽  
Author(s):  
Ju-Mi Jeong ◽  
Cheol-Hee Choi ◽  
Su-Kyeong Kang ◽  
In-Hwa Lee ◽  
Ji-Yoon Lee ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Oh Groups ◽  
Structure Activity ◽  
P Glycoprotein ◽  
Ic50 Values

Purpose. Flavonoids have been used as antioxidant, chemopreventive and chemosensitizing agents. In this study, eleven flavonoids containing a variety of hydroxy (OH) and/or methoxy (OMe) groups were evaluated for their antioxidant, cytotoxic and chemosensitizing effects to create a structure-activity relationship (SAR). Methods. 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radical solution-based chemical assay and and 2',7'-dichlorofluorescin diacetate (DCFH-DA) cellular-based assay were used to compare the free radical scavenging activity on the same molar concentration basis using the AML-2/DX100 cells which are characterized by the down-regulated expression of catalase and resulting supersensitiviy to hydrogen peroxide. The chemosensitization and cytotoxicity were determined by the MTT assay in the presence or absence of an anticancer drug using the P-glycoprotein-overexpressing AML-2 subline AML-2/D100 cells. Results. The antioxidant activity of the flavonoid (3,5,7,3’,4’-OH) was higher than that of the flavonoid (5,7,3’,4’-OH). Flavonoids substituted with the various number of OMe decreased antioxidant activity. Flavonoids with 7-OH or 5,7-OH groups have the highest cytotoxicity, and flavonoids with 5,7-OMe group intermediate cytotoxicity. The IC50 values of flavonoid (5,7-OMe, 3’,4’,5’-OMe) and flavonoid (5,7-OMe, 4’-OMe), 0.4 M and 1.4 M. The IC50 values of flavonoid (5,6,7-OMe, 3’,4’-OMe) and flavonoid (5,6,7-OMe, 3’,4’,5’-OMe), 3.2 uM and 0.9 M, respectively, and those of flavonoid (5,6,7-OMe, 3’,4’,5’-OMe) and flavonoid (5,7-OMe,3’,4’,5’-OMe) were 0.9 M and 0.4 M, respectively. Conclusions. These results suggest that flavonoids with 3-OH group play a positive role in antioxidant activities, flavonoids with 5-OH and/or 7-OH groups show the higher cytotoxicity, and flavonoids with 3’-OMe and/or 5’-OMe groups plays positive but 6-OMe groups negative roles in the P-glycoprotein (Pgp) inhibition. It is believed that these SAR results can be taken into account for the development of flavonoids with high therapeutic index.

scholarly journals Antioxidant Activity of Zyzzyanones and Makaluvamines from the Marine Sponge Zyzzya fuliginosa

2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Natalia K. Utkina
Keyword(s):  
Antioxidant Activity ◽  
Linoleic Acid ◽  
Marine Sponge ◽  
Antioxidant Activities ◽  
Side Chain ◽  
Scavenging Activity ◽  
Structural Variations ◽  
Abts Assay ◽  
Structure Activity Relationships ◽  
Structure Activity

Antioxidant activities of zyzzyanones A-D (1–4) and makaluvamines C (8), E (5), G (6), H (9), and L (7) isolated from the marine sponge Zyzzya fuliginosa (Carter, 1879) were evaluated using 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) scavenging assay and AAPH (2,2′-azobis(2-amidinopropane) dihydrochloride) induced autoxidation of linoleic acid. Zyzzyanones A, B (1, 2; TE = 0.3), C, D (3, 4; TE = 0.24) and makaluvamines 5–7 (TE = 0.6) displayed moderate activities in the ABTS assay and in the autoxidation of linoleic acid (61–66 % inhibition at concentrations of 0.1 mM). Makaluvamines C (8) and H (9) were essentially inactive in the both assays. Structure-activity relationships showed that antioxidant activities of tested compounds depended on the presence of a phenolic function in molecules. Makaluvamines 5–7 possessing a p-hydroxystyryl moiety were more active than zyzzyanones 1–4 possessing a p-hydroxyphenyl fragment. The presence of a charged side chain in 1 and 2 slightly increases their ABTS scavenging activity in comparison with compounds 3 and 4. Structural variations in a pyrroloquinoline skeleton of 5–7 and in a dipyrroloquinone core of 1–4 have no effect on activities.

Cytotoxic and antioxidant effects of methoxylated stilbene analogues on HepG2 hepatoma and Chang liver cells: Implications for structure activity relationship

2010 ◽  
Vol 30 (2) ◽  
pp. 138-144 ◽  
Author(s):  
AH Hasiah ◽  
AR Ghazali ◽  
JFF Weber ◽  
S. Velu ◽  
NF Thomas ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Antioxidant Activities ◽  
Structure Activity Relationship ◽  
Liver Cells ◽  
Activity Relationship ◽  
Hydroxyl Groups ◽  
Structure Activity ◽  
Total Antioxidant ◽  
Stilbene Analogues ◽  
Chang Liver

Stilbenes possess a variety of biological activities including chemopreventive activity. This study was conducted to evaluate the structural activity relationships of six methoxylated stilbene analogues with respect to their cytotoxic effects and antioxidant activities on HepG2 hepatoma and Chang liver cells. The cytotoxic and total antioxidant activities of six stilbene analogues were determined by MTT and Ferric Reducing Antioxidant Power (FRAP) assays, respectively. We found that the cis-methoxylated stilbene: (Z)-3,4,4'-trimethoxystilbene was the most potent and selective antiproliferative agent (IC50 89 µM) in HepG2 cells. For the total antioxidant activity, compounds possessing hydroxyl groups at the 4' position namely (E)-3-methoxy-4'-hydroxystilbene, (E)-3,5-dimethoxy-4'-hydroxystilbene (pterostilbene), (E)-4-methoxy-4'-hydroxystilbene showed the highest antioxidant activity. Structure activity relationship studies of these compounds demonstrated that the cytotoxic effect and antioxidant activities of the tested compounds in this study were structurally dependent.

scholarly journals Chemical Compounds, Physicochemical Properties, and Antioxidant Activity of A. cardamomum Leaves and Rhizomes Oils on Different Distillation Time

2020 ◽  
Vol 11 (1) ◽  
pp. 35-40
Author(s):  
Rini Pujiarti ◽  
Aisyah Kusumadewi
Keyword(s):  
Antioxidant Activity ◽  
Physicochemical Properties ◽  
Antioxidant Activities ◽  
Optical Rotation ◽  
Chemical Properties ◽  
Acid Number ◽  
Water Steam ◽  
Main Compound ◽  
Physico Chemical ◽  
Dpph Method

Amomum cardamomum is a local cardamom that grows widely and recently developed as and agroforestry crops in Indonesia. Its seeds, leaves and rhizomes are sources of essential oil. Essential oils from cardamom have many benefits for health and flavouring agent. The objectives of this study were to elucidate the yield, chemical composisition, physico-chemical properties, and antioxidant activities of leaves and rhizomes oils of cardamom were distillated using water-steam distillation for 4, 6, and 8 hours. The chemical composition were analyzed by GC-MS, physicochemical properties were analyzed used ISO standard and antioxidant activity were analyzed by DPPH method. The results showed that A. cardamomun oils yield between 0.06-0.33%. The main compound in the oils is 1,8-cineole with the highest percentage was obtained from cardamom rhizomes oil was distillated for 6 hours (60.63%). The results of each sample almost have the same quality with specific gravity between 0.899 – 0.909; refractive index between 1.476-1.478; optical rotation between (+)2.05⁰-(+)2.38⁰; miscibility in 70% alcohol between 1:7-1:9; and acid number between 0.49-0.69. The leaves and rhizomes oils of A. cardamomum showed potent antioxidant activity with the highest antioxidant were obtained from cardamom rhizomes oil were distillated for 8 hours with IC50: 0.039 g/ml.

Changes in physicochemical properties and antioxidant activity of fermented kepayang (Pangium edule Reinw.) seeds

Food Research ◽  
2021 ◽  
Vol 5 (4) ◽  
pp. 47-58
Author(s):  
N.H. Mustaffer ◽  
N.S. Ramli ◽  
K. Tongkhao ◽  
K. Vangnai ◽  
N.K. Rosni ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Physicochemical Properties ◽  
Total Phenolic Content ◽  
Phenolic Content ◽  
Ph Value ◽  
Antioxidant Activities ◽  
Radical Scavenging ◽  
Water Extract ◽  
Total Phenolic ◽  
Crude Fibre

One method for processing Pangium edule Reinw. seeds for consumption is fermentation. The aim of this study was to determine the physicochemical characteristics of P. edule Reinw. seeds during fermentation and antioxidant activity of the extracts. P. edule Reinw. seeds were boiled for 2 hrs and subjected to spontaneous fermentation for 40 days. The physicochemical properties were evaluated according to AOAC methods. Raw and fermented P. edule Reinw. seeds (day 40) were dried and extracted using ethanol and distilled water. The antioxidant activity was measured using 2,2-diphenyl-1- dipicrylhydrazyl (DPPH) radical scavenging assay while total phenolic content was measured by following the Folin-Ciocalteu method. The results showed that there were no significant differences in water activity while the pH value was decreased along fermentation days. The TSS was significantly increased from day 0 (11.00) to day 30 (19.50), however, it drastically decreased to 11.50 after 40 days of fermentation. The value of lightness (L*) parameter was decreased from 66.44 to 25.28 on day 40 but no significant differences for a* and b* parameter. For proximate analysis, the percentage of ash, crude protein, crude fat, and crude fibre were significantly increased while moisture content and carbohydrate were significantly decreased throughout the fermentation days. Besides, the highest DPPH activity was observed in the ferment-water extract at concentration 10 mg/mL which about 95.61% while the highest total phenolic content was obtained from the ferment-ethanol extract (173.79 mg GAE/100 mg). In conclusion, there were some changes in the physicochemical properties of P. edule Reinw. seeds during fermentation and potentially has antioxidant activities. The results of this study might be used as basic information to develop the fermented seeds as a functional food.

scholarly journals Computational Study of Ortho-Substituent Effects on Antioxidant Activities of Phenolic Dendritic Antioxidants

Antioxidants ◽  
2020 ◽  
Vol 9 (3) ◽  
pp. 189 ◽  
Author(s):  
Choon Young Lee ◽  
Ajit Sharma ◽  
Julius Semenya ◽  
Charles Anamoah ◽  
Kelli N. Chapman ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Electron Transfer ◽  
Antioxidant Activities ◽  
Computational Study ◽  
Radical Scavenging ◽  
Substituent Effects ◽  
Phenolic Antioxidants ◽  
Electronic Effects ◽  
Total Enthalpy ◽  
Structure Activity

Antioxidants are an important component of our ability to combat free radicals, an excess of which leads to oxidative stress that is related to aging and numerous human diseases. Oxidative damage also shortens the shelf-life of foods and other commodities. Understanding the structure–activity relationship of antioxidants and their mechanisms of action is important for designing more potent antioxidants for potential use as therapeutic agents as well as preservatives. We report the first computational study on the electronic effects of ortho-substituents in dendritic tri-phenolic antioxidants, comprising a common phenol moiety and two other phenol units with electron-donating or electron-withdrawing substituents. Among the three proposed antioxidant mechanisms, sequential proton loss electron transfer (SPLET) was found to be the preferred mechanism in methanol for the dendritic antioxidants based on calculations using Gaussian 16. We then computed the total enthalpy values by cumulatively running SPLET for all three rings to estimate electronic effects of substituents on overall antioxidant activity of each dendritic antioxidant and establish their structure–activity relationships. Our results show that the electron-donating o-OCH3 group has a beneficial effect while the electron-withdrawing o-NO2 group has a negative effect on the antioxidant activity of the dendritic antioxidant. The o-Br and o-Cl groups did not show any appreciable effects. These results indicate that electron-donating groups such as o-methoxy are useful for designing potent dendritic antioxidants while the nitro and halogens do not add value to the radical scavenging antioxidant activity. We also found that the half-maximal inhibitory concentration (IC50) values of 2,2-diphenyl-1-picrylhydrazyl (DPPH) better correlate with the second step (electron transfer enthalpy, ETE) than the first step (proton affinity, PA) of the SPLET mechanism, implying that ETE is the better measure for estimating overall radical scavenging antioxidant activities.

scholarly journals Antioxidant Activities of Vaccinium vitis-idaea L. Leaves within Cultivars and Their Phenolic Compounds

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 844 ◽  
Author(s):  
Lina Raudone ◽  
Gabriele Vilkickyte ◽  
Lina Pitkauskaite ◽  
Raimondas Raudonis ◽  
Rimanta Vainoriene ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Antioxidant Activities ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Positive Influence ◽  
Phenolic Profile ◽  
Structure Activity ◽  
The Subject ◽  
Potential Use

Lingonberry leaves are the subject of numerous studies because of antioxidant properties, positive influence on the health and potential use in the prevention and treatment of chronic diseases. In this work, the radical scavenging, reducing, chelating activities, and phenolic composition of ten lingonberry leaves cultivars, one subspecies, and one variety were investigated. Furthermore, the antioxidant activity of individual phenolic compounds, that can be found in lingonberry leaves, were analyzed, and structure-activity relationship was determined. Wide diversity for phenolic profile and antioxidant properties of lingonberry leaves has been observed in the present material. Cultivars ‘Kostromskaja rozovaja’, ‘Rubin’, and Vaccinium vitis-idaea var. leucocarpum surpassed all others tested cultivars and lower taxa by contents of phenolic compounds and antioxidant activity. Leaves of lingonberry cultivars and lower taxa are rich in arbutin, flavonol glycosides, proanthocyanidins, and the latter were considered to be the major contributor to antioxidant properties of lingonberry leaves.

Syntheses of Analogues of Propofol: A Review

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3693-3713 ◽  
Author(s):  
Ivaylo V. Dimitrov ◽  
Elina E. K. Suonio
Keyword(s):  
Antioxidant Activity ◽  
Soybean Oil ◽  
Mechanism Of Action ◽  
Critically Ill Patients ◽  
Lipid Emulsion ◽  
Water Solubility ◽  
Rapid Onset ◽  
Clinical Use ◽  
Structure Activity ◽  
Hypnotic Agent

AbstractPropofol (2,6-diisopropylphenol) is an intravenous sedative/hypnotic agent that is used extensively for introduction and maintenance of general anaesthesia, sedation of critically ill patients and procedural sedation (e.g., endoscopy). Propofol has a rapid onset and offset of action and shows only minimal accumulation upon prolonged use. Propofol is only sparingly soluble in water and is currently marketed in 10% soybean oil-based lipid emulsion. Propofol’s anaesthetic properties were discovered over forty years ago, and it has been in clinical use for over thirty years. The main use of propofol remains as an anaesthetic but, over the years, analogues have been developed with varying properties from anticancer, anticonvulsant and antioxidant. In addition, large synthetic efforts have been made towards improving propofol’s water-solubility, its activity, and elucidating its structure–activity­ relationship and exact mechanism of action have been made. This review provides an overview of the research pertaining to propofol-like molecules and covers the efforts of synthetic chemists towards propofol analogues over the last 40 years.1 Introduction2 History3 Early Work4 Improving Water Solubility5 The Importance of the Phenol6 Exploring the Structure–Activity Relationship and Attempts to Improve Activity7 Anticancer Activity8 Anticonvulsant Properties9 Antioxidant Activity10 Photoactive Labelling to Elucidate Mechanism of Action11 Photoregulation12 Conclusion

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