Development of Novel Antioxidants: Design, Synthesis, and Reactivity
| Autor: | Leonid L. Chepelev, James S. Wright, Gordana Babic, Helmi H. Hussain, and Alexandru Chichirau, Mihaela Flueraru, Tony Durst |
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| Rok vydání: | 2003 |
| Předmět: |
Models
Molecular Magnetic Resonance Spectroscopy Antioxidant Semiquinone DPPH medicine.medical_treatment Catechols Molecular Conformation Ethyl acetate Naphthalenes Chemical synthesis Antioxidants chemistry.chemical_compound Reaction rate constant Picrates Computational chemistry medicine Organic chemistry Reactivity (chemistry) Chemistry Biphenyl Compounds Organic Chemistry Biphenyl compound Kinetics Drug Design Thermodynamics Indicators and Reagents |
| Zdroj: | The Journal of Organic Chemistry. 68:7023-7032 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo0301090 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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