Development of novel antioxidants: design, synthesis, and reactivity. 2003

Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
Department of Chemistry, University of Ottawa, D'Iorio Hall, 10 Marie Curie Street, Ottawa, Canada K1N 6N5.

We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH(*) were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH(*), suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009281 Naphthalenes Two-ring crystalline hydrocarbons isolated from coal tar. They are used as intermediates in chemical synthesis, as insect repellents, fungicides, lubricants, preservatives, and, formerly, as topical antiseptics.
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D010851 Picrates Salts or esters of PICRIC ACID.
D002396 Catechols A group of 1,2-benzenediols that contain the general formula R-C6H5O2. Pyrocatechols,o-Dihydroxybenzenes,ortho-Dihydroxybenzenes,o Dihydroxybenzenes,ortho Dihydroxybenzenes
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D001713 Biphenyl Compounds Whitish aromatic crystalline organic compounds made up of two conjoined BENZENE rings. Compounds, Biphenyl

Related Publications

Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
June 2008, Journal of medicinal chemistry,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
September 2011, European journal of medicinal chemistry,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
July 2007, Free radical research,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
January 2010, Methods in molecular biology (Clifton, N.J.),
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
January 2008, Current pharmaceutical design,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
September 2003, Bioorganic & medicinal chemistry,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
November 2023, Pharmaceuticals (Basel, Switzerland),
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
September 2020, Bioconjugate chemistry,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
December 2004, The Journal of organic chemistry,
Helmi H Hussain, and Gordana Babic, and Tony Durst, and James S Wright, and Mihaela Flueraru, and Alexandru Chichirau, and Leonid L Chepelev
June 2000, The Journal of organic chemistry,
Copied contents to your clipboard!