Synthesis of New 2,5-Di-substituted 1,3,4-Oxadiazoles Bearing 2,6-Di-tert-butylphenol Moieties and Evaluation of Their Antioxidant Activity

Eleven new 2,6-di-tert-butyl-4-(5-aryl-1,3,4-oxadiazol-2-yl)phenols 5a–k were synthesized by reacting aryl hydrazides with 3,5-di-tert butyl 4-hydroxybenzoic acid in the presence of phosphorus oxychloride. The resulting compounds were characterized based on their IR, 1H-NMR, 13C-NMR, and HRMS data. 2,2-Diphenyl-1-picrylhydrazide (DPPH) and ferric reducing antioxidant power (FRAP) assays were used to test the antioxidant properties of the compounds. Compounds 5f and 5j exhibited significant free-radical scavenging ability in both assays.

• Publication year

  2014

• Venue

  Molecules

• Publication date

  2014-03-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.3390/molecules19033436PMID 24658568PMCID 6271237
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Spectrometric identification of organic compounds

  2013cited by this paper
• Synthesis and Bioassay of a New Class of Furanyl-1,3,4-Oxadiazole Derivatives

  2013cited by this paper
• Chlorine atom substitution influences radical scavenging activity of 6-chromanol.

  2012cited by this paper
• Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012

  2012cited by this paper
• Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

  2012cited by this paper
• Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of N-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives

  2012cited by this paper
• Comparison between antioxidant activity of 2,5-disubstituted 1,3,4-oxadiazoles containing heteroaromatic ring and aromatic ring at 2nd position

  2011cited by this paper
• Antimicrobial and antioxidant activity of the Ephedra sarcocarpa growing in Iran

  2011cited by this paper
• Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis(1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles.

  2011cited by this paper
• A Planar Conformation and the Hydroxyl Groups in the B and C Rings Play a Pivotal Role in the Antioxidant Capacity of Quercetin and Quercetin Derivatives

  2011cited by this paper
• Darbufelone, a novel anti-inflammatory drug, induces growth inhibition of lung cancer cells both in vitro and in vivo

  2010cited by this paper
• Redox-control of matrix metalloproteinase-1: a critical link between free radicals, matrix remodeling and degenerative disease.

  2010cited by this paper
• Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics.

  2007cited by this paper
• New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents.

  2006cited by this paper
• The chemistry behind antioxidant capacity assays.

  2005cited by this paper
• Inhibitory effects of multi-substituted benzylidenethiazolidine-2,4-diones on LDL oxidation.

  2004cited by this paper
• Mass spectrometric fragmentation pathways of isotope labeled 2,5-disubstituted-1,3,4-oxadiazoles and thiadiazoles

  2004cited by this paper
• Antioxidants during anticancer therapy

  2004cited by this paper
• QSAR study of dual cyclooxygenase and 5-lipoxygenase inhibitors 2,6-di-tert-butylphenol derivatives.

  2003cited by this paper
• Mechanism-based in vitro screening of potential cancer chemopreventive agents.

  2003cited by this paper
• Mass spectrometric study of some protonated and lithiated 2,5-disubstituted-1,3,4-oxadiazoles

  2003cited by this paper
• Antioxidant properties of lignans and ferulic acid from the resinous exudate of Larrea nitida

  2003cited by this paper
• Loss of isocyanic acid from the internal oxadiazole ring of protonated molecules of some 2,5-diaryl-1,3,4-oxadiazoles.

  2002cited by this paper
• Antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl.

  2002cited by this paper
• A role for free radicals and nitric oxide in delayed recovery in aged rats with chronic constriction nerve injury.

  2001cited by this paper
• Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 1. Thiazolone and oxazolone series.

  1999cited by this paper
• Synthesis and biological evaluation of 2,6-di-tert-butylphenol hydrazones as 5-lipoxygenase inhibitors.

  1998cited by this paper
• Natural antioxidants : chemistry, health effects, and applications

  1997cited by this paper
• The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay.

  1996cited by this paper
• Bond Dissociation Energies of O−H Bonds in Substituted Phenols from Equilibration Studies

  1996cited by this paper
• Use of a Free Radical Method to Evaluate Antioxidant Activity

  1995cited by this paper
• Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally-active, nonulcerogenic antiinflammatory agents.

  1993cited by this paper
• 2,6-Di-tert-butyl-4-(2′-thenoyl)phenol(R-830): A novel nonsteroidal anti-inflammatory agent with antioxidant properties

  1982cited by this paper
• Free-Radical Chemistry: Structure and Mechanism

  1974cited by this paper

• Synthesis and Antioxidant Properties of 1,3,4-Oxadiazole Derivatives of Benzoic and Monohydroxybenzoic Acids

  2025cites this paper
• 1-(2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl) Quinolin-1-ium Bromide

  2024cites this paper
• 8-benzimidazolyl coumarin-3-oxadiazoles – Synthesis, Docking studies and Anti-proliferative evaluation against breast cancer

  2023cites this paper
• Protective effect of symmetrical N‐heterocyclic 1,3,4‐oxadiazole and 1,3,4‐thiadiazole derivatives against Pepino mosaic virus of tomato

  2022cites this paper
• Synthesis, Molecular Docking Studies, Antimicrobial, Anticancer and Antioxidant Activity of Some Novel Mannich Bases of Isatin Scaffold

  2022cites this paper
• Synthesis, Characterization, Antimicrobial and Molecular Docking Study of Benzooxadiazole Derivatives

  2022cites this paper
• Recent Advancement in Synthesis and Bioactivities of 1,3,4-Oxadiazole.

  2022cites this paper
• Synthesis of 5‐[(1H‐indol‐3‐yl)methyl]‐1,3,4‐oxadiazole‐2(3H)‐thiones and their protective activity against oxidative stress

  2021cites this paper
• Synthesis, Characterization and Anticancer Activity of (5,1-Substituted)-3-(indoline-4-(thiophene-2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1H-imidazole-5-one Derivatives

  2021cites this paper
• Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives

  2021cites this paper
• In vivo acute toxicity and anti-gastric evaluation of a novel dichloro Schiff base: Bax and HSP70 alteration

  2019cites this paper
• A Review Exploring Therapeutic Worth of 1,3,4-Oxadiazole Tailored Compounds.

  2019cites this paper
• Gastroprotective activity of a novel Schiff base derived dibromo substituted compound against ethanol-induced acute gastric lesions in rats

  2019cites this paper
• Synthesis, Reactions and Antioxidant Activity of 5-(3', 4'-dihydroxy-tetrahydrofuran-2'-yl)-2-methyl-3-carbohydrazide

  2019cites this paper
• Isolation of Natural Naphthoquinones from Juglans regia and In Vitro Antioxidant and Cytotoxic Studies of Naphthoquinones and the Synthetic Naphthofuran Derivatives

  2018cites this paper
• Highly Efficient One-Pot Solvent-Free Synthesis of 2,5-Disubstituted-1,3,4-Oxadiazole via BTI-mediated Oxidation of N-Acylhydrazone from Hydrazide and Aldehyde

  2017cites this paper
• Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids

  2017cites this paper
• The Journal of Clinical Investigation

  2016cites this paper
• Phosphorylation state-dependent modulation of spinal glycine receptors alleviates inflammatory pain.

  2016cites this paper
• Rational Design and Synthesis of New, High Efficiency, Multipotent Schiff Base-1,2,4-triazole Antioxidants Bearing Butylated Hydroxytoluene Moieties

  2016cites this paper
• New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

  2015cites this paper