ChemInform Abstract: Synthesis and Antiviral Activity of 5‐Hydroxyindole Derivatives.

Panisheva, E. K.; Mikerova, N. I.; Nikolaeva, I. S.; Fomina, A. N.; Cherkasova, A. A.; Golovanova, E. A.; Krylova, L. Yu.

doi:10.1002/chin.198929132

Cited by 4 publications

(3 citation statements)

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“…Arbidol (ARB; ethyl-6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-indole-3-carboxylate hydrochloride monohydrate) was developed by the Russian Research Chemical Pharmaceutical Institute about 20 years ago [6], and since 1990 ARB has been used as an over-the-counter medicinal drug in Russia, primarily for prophylaxis and treatment of acute respiratory infections including influenza.…”

Section: Arb Structure and Synthesismentioning

confidence: 99%

Arbidol: A Broad-Spectrum Antiviral Compound that Blocks Viral Fusion

Boriskin

Ленева²,

Pécheur³

et al. 2008

CMC

369

316

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Arbidol (ARB; ethyl-6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-indole-3-carboxylate hydrochloride monohydrate), is a Russian-made potent broad-spectrum antiviral with demonstrated activity against a number of enveloped and non-enveloped viruses. ARB is well known in Russia and China, although to a lesser extent in western countries. Unlike other broad-spectrum antivirals, ARB has an established molecular mechanism of action against influenza A and B viruses, which is different from that of available influenza antivirals, and a more recently established mechanism of inhibition of hepatitis C virus (HCV). For both viral infections the anti-viral mechanism involves ARB inhibition of virus-mediated fusion with target membrane and a resulting block of virus entry into target cells. However, ARB inhibition of fusion exploits different ARB modalities in case of influenza viruses or HCV. This review aims to summarize the available evidence of ARB effects against different groups of viruses, also, to compare various aspects of ARB anti-fusion mechanisms against influenza virus and HCV (with reference to different stringency of pH-dependence of these two viral fusogens) and to discuss further prospects for ARB and its improved derivatives of the parent compounds.

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Section: Arb Structure and Synthesismentioning

confidence: 99%

Arbidol: A Broad-Spectrum Antiviral Compound that Blocks Viral Fusion

Boriskin

Ленева²,

Pécheur³

et al. 2008

CMC

369

316

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“…Arbidol, also known as umifenovir, is a broad-spectrum antiviral compound developed at the Russian Research Chemical and Pharmaceutical Institute about 25 years ago [ 6 ] and licensed in Russia and China for the prophylaxis and treatment of human influenza A and B infections, plus post-influenza complications [ 7 ]. Subsequently, arbidol was shown to be active against numerous DNA/RNA and enveloped/non-enveloped viruses [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Arbidol (Umifenovir): A Broad-Spectrum Antiviral Drug That Inhibits Medically Important Arthropod-Borne Flaviviruses

Haviernik

Štefánik

Fojtíková

et al. 2018

Viruses

109

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Arthropod-borne flaviviruses are human pathogens of global medical importance, against which no effective small molecule-based antiviral therapy has currently been reported. Arbidol (umifenovir) is a broad-spectrum antiviral compound approved in Russia and China for prophylaxis and treatment of influenza. This compound shows activities against numerous DNA and RNA viruses. The mode of action is based predominantly on impairment of critical steps in virus-cell interactions. Here we demonstrate that arbidol possesses micromolar-level anti-viral effects (EC50 values ranging from 10.57 ± 0.74 to 19.16 ± 0.29 µM) in Vero cells infected with Zika virus, West Nile virus, and tick-borne encephalitis virus, three medically important representatives of the arthropod-borne flaviviruses. Interestingly, no antiviral effects of arbidol are observed in virus infected porcine stable kidney cells (PS), human neuroblastoma cells (UKF-NB-4), and human hepatoma cells (Huh-7 cells) indicating that the antiviral effect of arbidol is strongly cell-type dependent. Arbidol shows increasing cytotoxicity when tested in various cell lines, in the order: Huh-7 < HBCA < PS < UKF-NB-4 < Vero with CC50 values ranging from 18.69 ± 0.1 to 89.72 ± 0.19 µM. Antiviral activities and acceptable cytotoxicity profiles suggest that arbidol could be a promising candidate for further investigation as a potential therapeutic agent in selective treatment of flaviviral infections.

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“…Actually, in the absence of substituents at position 3, for example, aminomethylation with bisdimethylaminomethane goes regioselectively at position 4 with yields close to quantitative [39][40][41], which could apparently be determined by purely steric factors. However, formation of the corresponding 4-isogramine (which has been proposed as an antiinflammatory agent) was also noticed for the 3-substituted 5-hydroxyindole 3-acetyl-5-hydroxy-2-(sulfanylmethyl)indole, in spite of the presence of the acetyl group at position 3 [42]. Regioselective dimethylaminomethylation at position 4, including cases where position 6 was free, has also been observed for a series of 1,2,3-trisubstituted 5-hydroxyindoles [43][44][45].…”

Section: Synthesis Of Indole Derivatives Containing a Dimethylaminomementioning

confidence: 95%

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

Семенов

Yurovskaya

2005

Chem Heterocycl Compd

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ChemInform Abstract: Synthesis and Antiviral Activity of 5‐Hydroxyindole Derivatives.

Abstract: Starting with the 5‐acetoxyindoles (I), the derivatives (II), (IV), (VI), (VII), (IX), and (X) are prepared by common methods.

Cited by 4 publications

References 0 publications

Arbidol: A Broad-Spectrum Antiviral Compound that Blocks Viral Fusion

Arbidol: A Broad-Spectrum Antiviral Compound that Blocks Viral Fusion

Arbidol (Umifenovir): A Broad-Spectrum Antiviral Drug That Inhibits Medically Important Arthropod-Borne Flaviviruses

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

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