Synthesis and Antiviral Activity of Substituted 2,4-bis-aminomethyl-5-hydroxy-1H-indole-3-carboxylic Acid Ethyl Esters and their Derivatives
| Autor: | Ya. A. Ivanenkov, Pavel M. Yamanushkin, V. M. Kisil, A. V. Ivashchenko, Ilya Okun, Andrey Alexandrovich Ivashchenko, Oleg D. Mitkin, O. M. Korzinov, V. Yu. Vedenskii, Elena A. Bulanova, I. A. Leneva, V. V. Bychko |
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| Rok vydání: | 2014 |
| Předmět: | |
| Zdroj: | Pharmaceutical Chemistry Journal. 48:569-581 |
| ISSN: | 1573-9031 0091-150X |
| Popis: | New substituted ethyl esters of 2,4-bis-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids, 8-aminomethyl-2-methyl-2,3-dihydro-1H,7H-[1,3]-oxazino-[5,6-e]indole-9-carboxylic acids, and members of the previously unknown 4,5-dihydro-1H-pyrrolo[4,3,2-de]isoquinolin-3-ones of 1,4-dihydropyrrolo[4,3,2-de]isoquinolin-3,6-diones were synthesized. Their cytotoxicities and antiviral activities against bovine viral diarrhea virus (BVDV), hepatitis C virus (HCV), and A/Aichi/2/69 (H3N2) were studied in vitro. These compounds were found not to be active against these viruses. The only exceptions were the hydrochlorides of the ethyl esters of 5-hydroxy-2-(dimethylaminomethyl)-1-methyl-6-pyridine-3-yl- and 5-hydroxy-2-(dimethylaminomethyl)-1-methyl-6-fluoro-1H-indole-3-carboxylic acids, which at micromolar concentrations not only produced effective suppression of influenza A/Aichi/2/69 (H3N2) virus replication in cell cultures, but also showed high in vivo efficacy in a model of influenza pneumonia in mice infected with influenza A/Aichi/2/69 (H3N2) virus at a dose of 25 mg/kg/day. |
| Databáze: | OpenAIRE |
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