In Silico Evaluation of Antioxidant Properties of Cinnamaldehyde Phenylhydrazone (original) (raw)
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Antioxidant Activities of Cinnamaldehyde Derivatives
IOP Conference Series: Materials Science and Engineering, 2018
The modification structures of cinnamaldehyde, which was isolated from cinnamon oil, has been carried out. The synthesized compounds were tested their antioxidant activity by using 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging assay and the IC50 was done by spectrophotometric assay method compared with standard vitamin E. The cinnamaldehyde derivatives, e.g. cinnamic acid 2, methyl cinnamate 3 and cinnamyl alcohol 5 had significantly higher antioxidant activity than that of their starting materials, cinnamaldehyde. However, although cinnamic amine 5 had a hydroxyl group, it gave no antioxidant activity possibly due to its bulky structure.
Oriental Journal of Chemistry, 2016
A series of N-cinnamoyl aryl hydrazones 2a-2i were synthesized in good yields by microwave irradiation technique. The title compounds were formed by nucleophilic condensation of various N 1-substituted benzylidene-2-cyano aceto hydrazides with N,N-dimethyl amino benzaldehyde. The intermediate N 1-substituted benzylidene-2-cyano aceto hydrazide was obtained by condensing various substituted benzaldehydes with cyanoacetohydrazide. The structures of the compounds were characterized by IR, 1 H NMR and Mass spectra. The antioxidant activity was studied by reduction of DPPH, scavenging of nitric oxide and hydrogen peroxide methods with ascorbic acid as the standard drug. The compounds were evaluated for cytotoxic activity by BSLT method and their ED 50 values were compared the standard podophyllotoxin. Among the compounds evaluated, N 1-benzylidene-2cyano-3-(4-dimethylamino) phenyl acrylo hydrazide (2a) and N 1-(4-methoxy-benzylidene)-2-cyano-3-(4-dimethylamino) phenyl acrylohydrazide (2e) showed good antioxidant activity towards all the three models .The compounds 2a and 2e showed ED 50 values 3.07 µg/ml and 3.7 µg/ml respectively which were compared against the standard podophyllotoxin (1.64 µg/ml).
ChemInform, 2011
A series of novel N-(α-benzamido cinnamoyl) aryl hydrazone derivatives 3a-m have been synthesized and screened for their anti-inflammatory and antioxidant activities. These compounds have been synthesized by refluxing intermediate α-benzamidocinnamhydrazide with substituted benzaldehydes in the presence of a few drops of glacial acetic acid. The intermediate αbenzamido-cinnamhydrazide is prepared by stirring 4-benzylidene-2-phenyl oxazole-5-one with hydrazine hydrate in presence of absolute ethanol. The chemical structures of the compounds are established by IR, 1 H NMR and mass spectral data. Of all the compounds screened, compound 3m N'-(5-bromo-4-hydroxy-3methoxybenzylidene)-2-(benzamido)-3-phenylacrylohydrazide shows anti-inflammatory activity (75%) which is equivalent to that produced by the same dose (100 mg/kg) of phenylbutazone (74%). Compound 3l N'-(4-hydroxy-3-methoxy benzylidene)-2-(benzamido)-3-phenyl acrylohydrazide, shows good antiinflammatory and antioxidant activity.
Study of antioxidant activity of selected monocarbohydrazone derivatives
Zastita materijala
Many of carbohydrazone derivatives have shown a wide range of biological activities. In previous studies, these compounds have proven to be excellent anti-cancer, antitumor, antibacterial, antimicrobial and antioxidant agents. Monocarbohydrazones, as one of the carbohydrazone derivatives, have been slightly explored. Due to that reason, in this study, eight newly synthesized monocarbohydrazones were subjected to examinations by the use of three antioxidant tests. To determine the effectiveness of monocarbohydrazone as potential radical scavengers, DPPH (2,2-Diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) and FRAP (Ferric Reducing Antioxidant Power) assays were used. The obtained results could open the door for further studies of these compounds as biologically active substances.
Antioxidant and Antibacterial Activity of Cinnamaldehyde Derivative
International Journal for Research in Applied Science and Engineering Technology (IJRASET), 2022
This study reports the antibacterial and antioxidant properties of cinnamaldehyde derivatives. DPPH, Superoxide Anion Radical, Hydroxy Radical, and Nitric Oxide Radical Scavenging Activities were used to assess the test compound's antioxidant capacity. The well diffusion method was used to examine the antibacterial efficiency against both Gram positive and Gram-negative microorganisms. Both Gram positive and Gram-negative bacterial strains responded favourably to the antibacterial effects of cinnamaldehyde derivatives. The study revealed the test substance possesses strong antibacterial and radical scavenging abilities.
Evaluation of Antioxidant Activity of Cinnamic Acid and Some of its Derivatives
European Chemical Bulletin
Cinnamic acid, chemically known as 3-phenyl-2-propenoic acid is has a broad spectrum of pharmacological actions including antioxidant activity. The esterification and selective reduction of the acid led to ethyl cinnamate and cinnamyl alcohol, respectively. Cinnamic acid demonstrated a poor antioxidant activity (IC50) of 1.2 µg mL-1 while ethyl cinnamate and cinnamyl alcohol elicited activities of 0.64 µg mL-1 (moderate) and 0.84 µg mL-1 , respectively. The obtained results indicate that esterification enhances the antioxidant activity of cinnamic acid.
In vitro and in silico studies of antioxidant activity of 2-thiazolylhydrazone derivatives
Journal of molecular graphics & modelling, 2018
The antioxidant potential of a series of thiazolylhydrazone derivatives was investigated using three different methods namely DPPH, ABTS and FRAP assays. In general, the tested compounds showed higher or comparable activity to that of curcumin, used as positive control. Chemometric analyses demonstrated that the presence of hydrazone moiety is required for the activity of this class of compounds. From these results, compound 4 was identified as the most promising molecule and was then selected for further studies. The antiproliferative effect of compound 4 was evaluated, being active in three (T47D, MDA-MB-231 and SKMEL) of the six cancer cell lines tested, with IC values ranging from 15.9 to 31.3 μM. Compound 4 exhibited no detectable cytotoxic effect on peripheral blood mononuclear cells (PBMC) when tested at a concentration of 100 μM, demonstrating good selectivity. From these results, it is possible to infer that there is a correlation between antioxidant capacity and anticancer...
Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation
Journal of agricultural …, 1999
The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2′-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids.
Antioxidant activity and structural features of Cinnamomum zeylanicum
The antioxidants in food materials have recently attracted researchers' attention because many reports have shown that the oxidative stress is closely related to the aging process of the cells and acts as a trigger to various diseases including cancer. Since reactive oxygen species (ROS) is involved in initiating and promoting several diseases such as cancer and cardiovascular events, this study was designed to evaluate the antioxidant capacity of pectic polysaccharides extracted from the bark of Cinnamomum zeylanicum, locally known as Daruchini. An arabinogalac-tan (A), one partly methyl esterified galacturonic acid (B) and a neutral glucan (C) were isolated. The glucan is made up of b-(1 ? 3)-linked glucopyranosyl residues and has a molecular mass of 7 kDa. The arabinogalactan is highly branched and has an average molecular mass of 40 kDa. The in vitro antioxidant capacity of the fractions was studied by ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays. The arabinogalactan (A) showed the highest potential followed by the uronic acid (B) and glucan (C). Taken together, these findings demonstrate that these polysaccharides could be used as natural antioxidants by the food industry.
The purpose of this study was to investigate the therapeutic activity of the cinnamic acid derivative KAD-3 (ethyl 3-(4-methoxyphenyl) acrylate) on Fe 2+-induced oxidative hepatic damage via experimental and computer aided studies. Methods: Oxidative hepatic damage was induced via incubation of tissue supernatant with 0.1 mM FeSO 4 for 30 min at 37 • C ex vivo with different concentration of KAD-3. Molecular docking, ADMET profiling, and density functional theory were conducted on the candidate to filter the properties of the drug candidate for drug design. Key findings: GSH, CAT, and ENTPDase activities were reduced when hepatic damage was induced (p < 0.05). In contrast, a significant increase in MDA levels and an increase in ATPase activity were observed. When compared to control levels, KAD-3 treatment reduced these levels and activities (p < 0.05). KAD-3 demonstrated good bond formation (− 5.8 kcal/mol, − 5.6 kcal/mol), drug-likeness (no rule violation), and electronic properties (chemically reactive) as compared to the standard (quercetin). Molecular docking, ADMET profiling, and density functional theory predict the functional attributes of the drug candidate against ATPase and ENTPDase targets. Conclusion: The findings from our study indicated that KAD-3 can protect against Fe 2+-induced hepatic damage by suppressing oxidative stress and purinergic activities.