Synthesis and Antiviral Activity of Ethyl 1,2-dimethyl-5-Hydroxy-1 H-Indole-3-carboxylates and Their Derivatives.

Autor: Ivashchenko, A., Yamanushkin, P., Mit'kin, O., Kisil', V., Korzinov, O., Vedenskii, V., Leneva, I., Bulanova, E., Bychko, V., Okun', I.
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Zdroj: Pharmaceutical Chemistry Journal; Mar2014, Vol. 47 Issue 12, p636-650, 15p
Abstrakt: New substituted ethyl 5-hydroxy-1,2-dimethyl-1 H-indole-3-carboxylates and 7,8-dimethyl-1,2,3,7-tetrahydro[1,3]oxazino[5,6- e]indole-9-carboxylates including arbidol analogs in addition to 6-hydroxy-1-methyl-7-pyridin-3-yl-4,5-dihydropyrrolo[4,3,2- de]isoquinolin-3(1 H)-ones and 1,4-dimethyl-7-pyridin-3-yl-2-(phenylsulfonylmethyl)-1,4-dihydropyrrolo[4,3,2- de]isoquinoline-3,6-dione were synthesized. Their antiviral activity against influenza A/New Caledonia/20/99 virus (HN), bovine viral diarrhea virus (BVDV), and hepatitis C virus (HCV) was studied. It was found that the synthesized compounds were not noticeably active against these viruses. The exceptions were only ethyl 5-hydroxy-4-(dimethylaminomethyl)-1-methyl-6-pyridin-3-yl-2-(phenylsulfinylmethyl)-1 H-indole-3-carboxylate and 5-hydroxy-1,2-dimethyl-6-fluoro-1 H-indole-3-carboxylate hydrochlorides, which exhibited micromolar activities EC = 6.6 and 9.8 ìM, respectively, against a human hepatoma cell line (Huh7.3) with increased sensitivity to HCV infection (strain JFH-1, genotype 2a). [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index