Synthesis and antiviral activity of indole and benzofuran sulfides

Zotova, S. A.; Korneeva, T. M.; Shvedov, V. I.; Fadeeva, N. I.; Leneva, I. A.; Fedyakina, I. Т.; Khristova, Marina L.; Nikolaeva, I. S.; Peters, V. V.; Gus'kova, T. A.

doi:10.1007/bf02219467

Cited by 19 publications

(14 citation statements)

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“…In this direction, because of the pharmacological uses of benzofurans, the syntheses and pharmacological properties of benzofuran derivatives have been extensively investigated [1][2][3][4]. Previously we have shown that catechols can be oxidized electrochemically to o-quinones.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation of catechols in the presence of acetylacetone

Nematollahi

Rafiee

2004

Journal of Electroanalytical Chemistry

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Section: Introductionmentioning

confidence: 99%

Electrochemical oxidation of catechols in the presence of acetylacetone

Nematollahi

Rafiee

2004

Journal of Electroanalytical Chemistry

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“…Antiviral activity of the compounds synthesized here against influenza A/Aichi/2/69 (H3N2) was determined by immunoenzyme analysis (IEA) in MDCK (Madin-Darby canine kidney) cell cultures as described in [4,14]. A total of 8 -10 serial three-fold dilutions from concentrations of 100 to 0.1 mM were prepared.…”

Section: Cytotoxicity and Antiviral Activity Against Hepatitis C Virumentioning

confidence: 99%

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

et al. 2015

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Novel substituted 5-hydroxy-2-aminomethyl-1H-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-1H-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.Keywords: 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids, antiviral activity, antiinfluenza activity, influenza A/Aichi/2/69 (H3N2), BVDV, HCV.Substituted 2-and 4-aminomethyl-5-hydroxyl-1H-indole-3-carboxylic acids are known to have some degree of antiviral activity [1 -3]. In particular, 1-benzyl-2-dimethylaminomethyl-3-carbethoxy-5-acetoxy-6-bromoindole hydrochloride demonstrated antiinfluenza activity in studies using a mouse model of influenza pneumonia [3]. We have previously described the synthesis and antiviral activity of a series of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids and have shown them to have limited activity against influenza A/New Caledonia/20/99 (H1N1) virus, bovine viral diarrhea virus (BVDV), and HCV [4].We describe here the synthesis and antiviral activities of novel derivatives of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids (compounds 4 -7, 11, 16 -20, 24). Substituted ethyl esters of 2-aminomethyl-5-hydroxy-1H-indole-3-carboxylic acids 4 -7 were prepared (scheme 1) from 1-substituted ethyl esters of 5-hydroxy-2-methyl-1H-indole-3-carboxylic acids 1a -e, which, by analogy [5] with 1,2-dimethylindole (compound 1a), were sequentially converted to 5-acetyloxy-(compounds 2a -e) and 5-acetyloxy-6-bromoindoles (compounds 3a -e). Interaction of these latter compounds with dimethylamine, pyrrolidine, and morpholine gave the corresponding 2-aminomethyl-6-bromoindoles (4a -g). 6-Bromoindoles 4b,c were hydrogenated with hydrogen on 10% Pd/C to form indoles unsubstituted at position 6 (compounds 5a, b); reaction of 6-bromoindole 4a with copper (I) cyanide in N-methylpyrrolidone (NMP) produced the corresponding 6-cyanoindole compound 6, while use of

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“…Of course, the only possibility for 1,2,3,6-tetrasubstituted [46][47][48][49][50][51][52] and 1,2,3,6,7-pentasubstituted [18] 5-hydroxyindoles is dimethylaminomethylation at position 4. This method was used for the synthesis of arbidol, labelled with C 14 at position 2 and at the ethoxycarbonyl group, in order to study its pharmacokinetics [53].…”

Section: Synthesis Of Indole Derivatives Containing a Dimethylaminomementioning

confidence: 99%