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Bioorg Med Chem ; 21(24): 7699-708, 2013 Dec 15.
Article in English | MEDLINE | ID: mdl-24216089

ABSTRACT

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.


Subject(s)
Antiviral Agents/metabolism , Antiviral Agents/pharmacology , Catechols/metabolism , Catechols/pharmacology , Influenza A virus/drug effects , Monophenol Monooxygenase/metabolism , Animals , Antioxidants/chemistry , Antioxidants/metabolism , Antioxidants/pharmacology , Antiviral Agents/chemistry , Catechols/chemistry , Chickens , Dogs , Dose-Response Relationship, Drug , Epithelial Cells/drug effects , Epithelial Cells/virology , Erythrocytes/drug effects , Erythrocytes/virology , Humans , Hydrophobic and Hydrophilic Interactions , Microbial Sensitivity Tests , Oxidation-Reduction , Structure-Activity Relationship
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