Abstract
Regio- and enantioselective synthesis of (S)-(+)-3-arylamino-1-chloropropan-2-ols has been achieved by the epoxide ring opening of (±)-epichlorohydrin with different aromatic amines in the presence of Candida rugosa lipase. Activities of seven model (S)-(+)-3-arylamino-1-chloropropan-2-ols, out of 10 compounds synthesized, have been evaluated for the inhibition of tumor necrosis factor-α TNF-α) induced expression of intercellular adhesion molecule-1 (ICAM-1), which is one of the factors responsible for the modulation of inflammation in biological systems; (S)-(+)-1-chloro-3-(2'-chlorophenylamino)-propan-2-ol has been found to exhibit highest activity, that is, 86% inhibition of TNF-α induced expression of ICAM-1 at a concentration of 40 μg/ml.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Inflammatory Agents / chemical synthesis
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / pharmacology
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Biocatalysis
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Cell Adhesion / drug effects
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Endothelial Cells / cytology
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Endothelial Cells / drug effects
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Epichlorohydrin / chemistry*
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Humans
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Hydrocarbons, Chlorinated / chemical synthesis
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Hydrocarbons, Chlorinated / chemistry
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Hydrocarbons, Chlorinated / pharmacology
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Intercellular Adhesion Molecule-1 / biosynthesis*
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Lipase / chemistry
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Lipase / metabolism
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Propanols / chemical synthesis*
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Propanols / chemistry
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Propanols / pharmacology*
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Structure-Activity Relationship
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Tumor Necrosis Factor-alpha / antagonists & inhibitors*
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Tumor Necrosis Factor-alpha / metabolism
Substances
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Anti-Inflammatory Agents
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Hydrocarbons, Chlorinated
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Propanols
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Tumor Necrosis Factor-alpha
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Epichlorohydrin
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Intercellular Adhesion Molecule-1
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Lipase