Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid (original) (raw)
Related papers
Antioxidant and antifungal properties of benzimidazole derivatives
Zeitschrift fur Naturforschung. Section C, Biosciences
Antioxidant and radical scavenging properties of a series of 2-[4-(substituted piperazin-/piperidin-1-ylcarbonyl)phenyl]-1H-benzimidazole derivatives were examined. Free radical scavenging properties of compounds 11-30 and 33 were evaluated for the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide anion radical. In addition the inhibitory effects on the NADPH-dependent lipid peroxidation levels were determined by measuring the formation of 2-thiobarbituric acid reactive substances (TBARS) using rat liver microsomes. Compound 33 which has a p-fluorobenzyl substitutent at position 1 exhibited the strongest inhibition (83%) of lipid peroxidation at a concentration of 10(-3) M, while the nonsubstituted analogue 13 caused 57% inhibition. This result is fairly consistent with the antimicrobial activity results against both Staphylococcus aureus and Candida albicans.
Elsevier, 2024
Ferulic acid and p-coumaric acid, cinnamic derivatives of phenolic acid, have antibacterial, prooxidant, and antioxidant effects. In this study ferulic acid and p-coumaric acid amide derivatives were investigated for their antibacterial and antioxidant properties are described in this communication. The most effective conjugates against B subtilis were 5b (IC 50 : 215 AE 1.3 μM) and 4d (IC 50 : 336 AE 2.7 μM) and against P. aeruginosa were 4b (IC 50 : 365 AE 2.8 μM) and 5b (IC 50 : 341 AE 3.6 μM), whereas the none of conjugates were more effective against E. coli than reference Kanamycin. Conjugates 5b was the most effective against B subtilis of all the synthesized conjugates, with IC 50 values of (IC 50 : 215 AE 1.3 μM). The free radical scavenging capacity of each compound was determined using the DPPH and ABTS assays. Conjugates 4b (IC 50 : 53 AE 3.6 μM), 4c (IC 50 : 58 AE 1.3 μM), 4d (IC 50 : 57 AE 2.5 μM), 5b (IC 50 : 29 AE 1.5 μM) and 4a (IC 50 : 56 AE 4.3 μM) have greater antioxidant capacity than ferulic acid and ascorbic acid in the DPPH assay. Whereas in the ABTS assay, compounds 4b (IC 50 : 7 AE 1.8 μM), 5b (IC 50 : 5 AE 0.7 μM), 4a (IC 50 : 9 AE 3.2 μM), 4g (IC 50 : 7 AE 2.3 μM), and 5a (IC 50 : 8 AE 4.3 μM) showed more antioxidant activity than ferulic acid, p-coumaric acid and ascorbic acid. Thus, a large library of compounds derived from bile acid can be easily synthesized for extensive structure-activity relationship studies in order to identify the most appropriate antibacterial and antioxidant agents.
Synthesis, antioxidant and radical scavenging activities of novel benzimidazoles
Journal of Enzyme Inhibition and Medicinal Chemistry, 2005
The synthesis and antioxidant evaluation of some novel benzimidazole derivatives (10 -24) are described. Antioxidant properties of the compounds were investigated employing various in vitro systems viz., microsomal NADPH-dependent inhibition of lipid peroxidation (LP), interaction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and scavenging of superoxide anion radical. Compounds 12 and 13 showed very good antioxidant capacity and were 17-18 -fold more potent than BHT (IC 50 2.3 £ 10 24 M) with 1.3 £ 10 25 M and 1.2 £ 10 25 M IC 50 values, respectively, by interaction of the stable DPPH free radical.
Synthesis and evaluation of new phenolic derivatives as antimicrobial and antioxidant agents
Monatshefte für Chemie - Chemical Monthly, 2017
New phenolic derivatives bearing hydrazine and 1,3,4-oxadiazole moieties were synthesized and evaluated for their in vitro antimicrobial and antioxidant activities. Most of the compounds revealed pronounced activity against Pseudomonas aeruginosa as well as promising antioxidant activities. N 1-(2,5-Dihydroxybenzoyl)-N 2-(4methylphenylsulfonyl)hydrazine displayed promising activity against Escherichia coli and P. aeruginosa. N 1-(2,5-Dihydroxybenzoyl)-N 2-(2-naphthalenylmethylene)hydrazine was almost equipotent to the standard antioxidant vitamin C having scavenging activities of 84 and 93%, respectively. In vitro cytotoxicity study revealed that N 1-(2,5-dihydroxybenzoyl)-N 2-(2,3,4-trimethoxyphenylmethylene)hydrazine, N 1-(2,5-dihydroxybenzoyl)-N 2-(3,4,5trimethoxyphenylmethylene)hydrazine, and N 1-(2,5-dihydroxybenzoyl)-N 2-(4-methylphenylsulfonyl)hydrazine are more safe than reference 5-fluorouracil. In silico drug relevant properties proposed that all compounds have high to moderate drug-likeness scores. Accordingly, these derivatives can be potential leads for development of potent antimicrobial and antioxidant agents.
Arabian Journal of Chemistry, 2017
The oxadiazole pharmacophore is considered a viable lead structure for the synthesis of more efficacious and broad spectrum antimicrobial agents. The significance of this study was to prepare various oxadiazole derivatives by introducing the 1,3,4 oxadiazole core into several molecules to explore the possibilities of some altered biological activities. Therefore, the study presents the synthesis, antimicrobial and antioxidant evaluation of a series of 1,3,4 substituted oxadiazole derivatives. Antimicrobial evaluation revealed that eighteen compounds were able to display variable growth inhibitory effects on the tested Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus, Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli and fungal strains Candida albicans and Aspergillus niger. Among the synthesized derivative analogues 6f, 6l and 6r were found to be the most effective antibacterial agents. While the compounds 6c, 6l and 6q were found to be the most promising antifungal agents. On the other hand, all the synthesized compounds 6a-6r were subjected to antioxidant activity but only analogues 6l and 6q were found to exhibit potent antioxidant activity. Further compound 6l containing p-nitro phenyl moiety along with oxadiazole pharmacophore proved to be the most active antimicrobial and antioxidant agent.
Synthesis, Antimicrobial and Antioxidant Activities of Some Benzimidazole Derivatives
Letters in Drug Design Amp Discovery, 2009
A series of derivatives of trans-3-(2,4,6-trimethoxyphenyl)4,5-dihydroisoxazolo-4,5bis[carbonyl-(4 phenyl)thiosemicarbazide (9) and of trans-3-(2,4,6-trimethoxyphenyl)-4,5-dihydro isoxazolo-4,5-bis(aroylcarbohydrazide) (10a-c) were synthesized from trans-3-(2,4,6-trimethoxyphenyl)-4,5-dihydro-4,5-bis(hydrazenocarbonyl)isoxazole (8). The structures of the compounds were elucidated by both elemental and spectral (IR, NMR, and MS) analysis. Compound 9 shows activity against some bacterial species. No antibacterial activities were observed for compounds 10a-c. The antioxidant activity of the new compounds has been screened. Compound 9 showed higher antioxidant activity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2'-azino-bis(3-ethylbenzoline-6-sulfonic acid) diammonium salt methods.
Turkish Journal of Chemistry, 2015
Some novel 2-(substitutedbenzylthio)-5-((2-(4-substitutedphenyl)-1 H-benzo[d]imidazol-1-yl)methyl)-1,3,4oxadiazoles (5-12) and 2-(2-(4-chlorophenyl)-1 H-benzo[d]imidazol-1-yl)-N ′-(arylmethylene)acetohydrazide derivatives (13-22) were prepared and their in vitro antioxidant properties were investigated by determination of rat liver microsomal NADPH-dependent inhibition of lipid peroxidation (LP) levels and microsomal ethoxyresorufin O-deethylase (EROD) activity. Compound 18 was found to be the most active compound with 100% inhibition on LP level and 92% inhibition on EROD. Compounds 4b, 17, and 19 showed the strongest inhibitory effect (97%) on EROD. The free radical scavenging capacities of the compounds were also tested in vitro determining the interaction of the stable free radical 2,2,diphenyl-1-picrylhydrazyl (DPPH), and compounds 4a and 4b exhibited good antioxidant activities.
Antioxidant and antimicrobial evaluation of pyrimido [1, 2-a] benzimidazoles
When ethyl 2-cyano-3,3-bis(methylthio)acrylate (2) on treatment with 2-amino benzimidazole (1) in N,Ndimethyl formamide (DMF) and catalytic amount of anhydrous potassium carbonate, gives 3-cyano-2metylthio-4-oxo-4H-pyrimido [1,2-a] benzimidazole (3).The latter were further reacted with selected N-,O-and C-nucleophiles such as aryl amines, heteryl amines, substituted phenols and compounds containing an active methylene group to afforded 2-cyano-3-metylthio-4-oxo-4H-pyrimido [1,2-a] benzimidazole and their 2substituted derivatives. All newly synthesized compounds were evaluated and characterized by spectroscopic techniques and screened their very excellent antioxidant and antimicrobial activities.
Synthesis and evaluation ofin vitroantioxidant capacities of some benzimidazole derivatives
Journal of Enzyme Inhibition and Medicinal Chemistry, 2006
New, except 1d, melatonin analogue benzimidazole derivatives were synthesized and characterized in the present study. The potential role of melatonin as an antioxidant by scavenging and detoxifying ROS raised the possibility that compounds that are analogous to melatonin can also be used for their antioxidant properties. Therefore the antioxidant effects of the newly synthesized compounds were investigated in vitro by means of their inhibitory effect on hydrogen peroxide-induced erythrocyte membrane lipid peroxidation (EMLP) and on various erythrocyte antioxidant enzymes viz. superoxide dismutase (SOD), catalase (CAT) and glucose-6-phosphate dehydrogenase (G6PD). The synthesized benzimidazole derivatives showed remarkable antioxidant activity in vitro in the H 2 O 2-induced EMLP system. Furthermore their effects on various antioxidant enzymes are discussed and evaluated from the perspective of structure-activity relationships.