Synthesis and Antiviral Activity of Substituted Ethyl-2-Aminomethyl-5-Hydroxy-1H-Indole-3-Carboxylic Acids and Their Derivatives

Novel substituted 5-hydroxy-2-aminomethyl-1 H -indole-3-carboxylic acids and their derivatives were synthesized. The antiviral properties of these compounds were investigated in relation to bovine viral diarrhea virus (BVDV), hepatitis C virus (HCV), and influenza A/Aichi/2/69 (H3N2) virus. Of the c...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2015-06, Vol.49 (3), p.151-162
Main Authors: Ivachtchenko, A. V., Yamanushkin, P. M., Mitkin, O. D., Kisil, V. M., Korzinov, O. M., Vedenskii, V. Yu, Leneva, I. A., Bulanova, E. A., Bichko, V. V., Okun’, I. M., Ivashchenko, A. A., Ivanenkov, Ya. A.
Format: Article
Language:English
Subjects:
Antiviral agents
Bovine viral diarrhea virus
Diarrhea
Hepatitis C virus
Medicine
Organic acids
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
Search for New Drugs
Virus diseases
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Summary:Novel substituted 5-hydroxy-2-aminomethyl-1 H -indole-3-carboxylic acids and their derivatives were synthesized. The antiviral properties of these compounds were investigated in relation to bovine viral diarrhea virus (BVDV), hepatitis C virus (HCV), and influenza A/Aichi/2/69 (H3N2) virus. Of the compounds synthesized here, only the 5-hydroxy-2-(dimethylaminomethyl)-1-methyl-6-pyridin-3-yl- and 5-hydroxy-2-(dimethylaminomethyl)-1-methyl-6-fluoro-1 H -indole-3-carboxylic acid ethyl ester hydrochlorides had significant activity against these viruses, these agents not only suppressing the replication of influenza A/Aichi/2/69 (H3N2) virus in cell cultures at micromolar concentrations, but also demonstrating high efficacy, greater than that of Arbidol, in a model of influenza pneumonia in mice infected with influenza A/Aichi/2/69 (H3N2) virus, when given at a dose of 25 mg/kg/day.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-015-1244-6