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Электронная энциклопедия «Дискурсология»
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1.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4-benzotriazines [Electronic resource] / S. K. Kotovskaya, G. A. Zhumabaeva, N. M. Perova, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, N. I. Bormotov, S. M. Balakhnin, O. A. Serova // Pharmaceutical Chemistry Journal. - 2007. - Vol. 41, № 2. - P62-68. - Библиогр. : с. 68 (18 назв.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: New synthetic approaches to fluorinated 3-phenyl-1,2,4-benzotriazines for biological testing have been elaborated. 1-(3,4-Difluorophenyl)-3,5-diphenylformazan (IVa) was synthesized via dinitriding of 3,4-difluoroaniline, followed by azo-addition of the resulting azobenzenediazonium chloride with acetaldehyde phenylhydrazone. 6,7-Difluoro-3-phenyl-1,2,4-benzotriazine (Va) was obtained via intramolecular cyclization of formazan IVa in the presence of BF3/AcOH complex. Monofluoro-substituted 6-R-7-fluoro-3-phenyl-1,2,4-benzotriazine derivatives (Vb-Vq) were prepared by substituting fluorine atom with alkoxides in 3,4-difluoronitrobenzene. Conditions for nucleophilic substitution of the second fluorine atom in benzotriazines V have been established. Fluorinated 3-phenyl-1,2,4-benzotriazines have been tested for antiviral and cytotoxic activity on Vero cell cultures and proved to be active against severe diseases caused by smallpox and some other pathogenic viruses. ??

\\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2007, 41 (2), 62.pdf
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2.
Инвентарный номер: нет.
   
   A 62

   
    Antiviral Properties, Metabolism, and Pharmacokinetics of a Novel Azolo-1,2,4-Triazine-Derived Inhibitor of Influenza A and B Virus Replication [Text] / I. L. Karpenko, S. L. Deev, O. I. Kiselev, V. N. Charushin, V. L. Rusinov, E. N. Ulomskii, E. G. Deeva, O. N. Chupakhin // Antimicrobial Agents and Chemotherapy. - 2010. - Vol. 54, № 5. - P2017-2022
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Influenza viruses of types A and B cause periodic pandemics in the human population. The antiviral drugs approved to combat influenza virus infections are currently limited. We have investigated an effective novel inhibitor of human influenza A and B viruses, triazavirine {2-methylthio-6-nitro-1,2,4-triazolo[5,1-c]-1,2,4-triazine-7(4I)-one} (TZV). TZV suppressed the replication of influenza virus in cell culture and in chicken chorioallantoic membranes, and it protected mice from death caused by type A and B influenza viruses. TZV was also effective against a rimantadine-resistant influenza virus strain and against avian influenza A virus H5N1 strains. The pharmacokinetic parameters and bioavailability of TZV were calculated after the administration of TZV to rabbits. The TZV metabolite AMTZV {2-methylthio-6-amino-1,2,4-triazolo[5,1-s]-1,2,4-triazin(e)-7(4I)-one} was discovered in IAK 293T and Huh7 cell cultures, a liver homogenate, and rabbit blood after intragastric administration of TZV. AMTZV was nontoxic and inactive as an inhibitor of influenza virus in cell culture. Most likely, this metabolite is a product of TZV elimination

\\\\expert2\\nbo\\Antimicrobal Agents and Chemotherapy\\2010. V. 54, N 5. P. 2017-2022.pdf
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3.
Инвентарный номер: нет.
   

   
    Chemo-Enzymatic Synthesis and Biological Evaluation of 5,6-Disubstituted Benzimidazole Ribo- and 2′-Deoxyribonucleosides / I. D. Konstantinova, O. M. Selezneva, S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, A. V. Baranovsky // Synthesis. - 2012. - Vol.45. - Article in press
Кл.слова (ненормированные):
5,6-DISUBSTITUTED BENZIMIDAZOLES -- NUCLEOSIDES -- PURINE NUCLEOSIDE PHOSPHORYLASE
Аннотация: A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic- bases showed good substrate activity for PNP and the ribo- and 2′-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-D-ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-D-ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2-deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cy

\\\\expert2\\nbo\\Synthesis\\2012, Article in press.pdf
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4.
Инвентарный номер: нет.
   
   A 10

   
    A new antiviral drug triazavirin: Results of phase II clinical trial [Электронный ресурс] / O. I. Kiselev, E. G. Deyeva, T. I. Melnicova, K. N. Kozeletskaia, A. S. Klselev, V. L. Rusinov, V. N. Charushin, O. N. Chupakhin // Voprosy Virusologii . - 2012. - Vol.57, №6. - P9-12
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CLINICAL TRIAL -- EFFICACY -- INFLUENZA
Аннотация: The results of the clinical trial testing the efficacy of a new anti-influenza drug Triazavirin are presented in this work. The data of the trial were gathered during the 2010 influenza season. The treatment with oral Triazavirin significantly reduced the duration of the main clinical symptoms of influenza (intoxication, fever, respiratory symptoms), decreased the incidence of the influenza-related complications and the use of symptomatic drugs. The re-isolation rate of the influenza A and B viruses was significantly lower in the patients who were using Triazavirin. The analysis of the clinical data showed that the optimal prescribed dosage was 250 mg 3 times a day. -------------------------------------------------------------------------------- Reaxys Database Information|

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5.
Инвентарный номер: нет.
   
   A 62

   
    Antiviral properties, metabolism, and pharmacokinetics of a novel azolo-1,2,4-triazine-derived inhibitor of influenza A and B virus replication [Электронный ресурс] / I. L. Karpenko, S. L. Deev, O. I. Kiselev, V. N. Charushin, V. L. Rusinov, E. N. Ulomskii, E. G. Deeva, M. K. Kukhanova // Antimicrobial Agents and Chemotherapy . - 2010. - Vol.54, №5. - P2017-2022
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ANIMAL CELL -- ANIMAL EXPERIMENT -- ANTIVIRAL ACTIVITY
Аннотация: Influenza viruses of types A and B cause periodic pandemics in the human population. The antiviral drugs approved to combat influenza virus infections are currently limited. We have investigated an effective novel inhibitor of human influenza A and B viruses, triazavirine {2-methylthio-6-nitro-1,2,4- triazolo[5,1-c]-1,2,4-triazine-7(4Í)-one} (TZV). TZV suppressed the replication of influenza virus in cell culture and in chicken chorioallantoic membranes, and it protected mice from death caused by type A and B influenza viruses. TZV was also effective against a rimantadine-resistant influenza virus strain and against avian influenza A virus H5N1 strains. The pharmacokinetic parameters and bioavailability of TZV were calculated after the administration of TZV to rabbits. The TZV metabolite AMTZV {2-methylthio-6-amino-1,2,4- triazolo[5,1-s]-1,2,4-triazin(e)-7(4Í)-one} was discovered inÍÅK 293T and Huh7 cell cultures, a liver homogenate, and rabbit blood after intragastric administration of TZV. AMTZV was nontoxic and inactive as an inhibitor of influenza virus in cell culture. Most likely, this metabolite is a product of TZV elimination

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6.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4- benzotriazines [Электронный ресурс] / S. K. Kotovskaya, G. A. Zhumabaeva, N. M. Perova, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, O. A. Serova // Pharmaceutical Chemistry Journal. - 2007. - Vol.41, №2. - P62-68
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CYCLIZATION -- CYTOTOXICITY -- FLUORINATION
Аннотация: New synthetic approaches to fluorinated 3-phenyl-1,2,4-benzotriazines for biological testing have been elaborated. 1-(3,4-Difluorophenyl)-3,5- diphenylformazan (IVa) was synthesized via dinitriding of 3,4-difluoroaniline, followed by azo-addition of the resulting azobenzenediazonium chloride with acetaldehyde phenylhydrazone. 6,7-Difluoro-3-phenyl-1,2,4-benzotriazine (Va) was obtained via intramolecular cyclization of formazan IVa in the presence of BF3/AcOH complex. Monofluoro-substituted 6-R-7-fluoro-3-phenyl-1,2,4- benzotriazine derivatives (Vb-Vq) were prepared by substituting fluorine atom with alkoxides in 3,4-difluoronitrobenzene. Conditions for nucleophilic substitution of the second fluorine atom in benzotriazines V have been established. Fluorinated 3-phenyl-1,2,4-benzotriazines have been tested for antiviral and cytotoxic activity on Vero cell cultures and proved to be active against severe diseases caused by smallpox and some other pathogenic viruses

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7.
Инвентарный номер: нет.
   
   F 70

   
    Fluorinated derivatives of benz[4,5]imidazo[2,1-b][1,3]thiazoles are inhibitors of measles viruses [Электронный ресурс] / A. G. Pokrovskii, E. A. Il"ichyova, S. K. Kotovskaya, S. A. Romanova, V. N. Charushin, O. N. Chupakhin // Doklady Akademii Nauk . - 2004. - Vol.398, №3. - P412-414
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ANTIVIRAL ACTIVITY -- CYTOTOXICITY -- FLUORINATED BENZIMIDAZOLES
Аннотация: The results of in vitro anti-virus activity investigation for the new benzimidazoles (their synthesis is reported previously) are presented. The activity of the most active compound was studied in dependence of its introduction to the culture (before virus adsorption, simultaneously with virus, directly after virus adsorption, after 6 hours and after 1 day). Preliminary treatment of cells didn't protect them from further infecting; therewith the compound introduction simultaneously with virus or after infection caused no considerable effect on its anti-virus activity. The latter is attributed to blocking of late stages of measles virus reproduction - synthesis or arrangement of virus proteins

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8.
Инвентарный номер: нет.
   
   C 51

   
    Chemo-enzymatic synthesis and biological evaluation of 5,6-disubstituted benzimidazole ribo- and 2′-deoxyribonucleosides [Электронный ресурс] / I. D. Konstantinova, O. M. Selezneva, I. V. Fateev, T. A. Balashova, S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, I. A. Mikhailopulo // Synthesis (Germany). - 2013. - Vol.45, №2, art. N SS-2012-T0784-OP. - P272-280
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
5,6-DISUBSTITUTED BENZIMIDAZOLES -- NUCLEOSIDES -- SUBSTRATE PROPERTIES
Аннотация: A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic bases showed good substrate activity for PNP and the ribo- and 2-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-d- ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-d- ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2- deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cytotoxicity

\\\\expert2\\nbo\\Synthesis\\2013, v. 45. N 2. p. 272-280.pdf
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9.
Инвентарный номер: нет.
   

   
    Chemo-Enzymatic Synthesis and Biological Evaluation of 5,6-Disubstituted Benzimidazole Ribo- and 2′-Deoxyribonucleosides / I. D. Konstantinova, O. M. Selezneva, S. K. Kotovskaya, Z. M. Baskakova, V. N. Charushin, A. V. Baranovsky // Synthesis. - 2013. - Vol.45, № 2. - С. 272-280
Кл.слова (ненормированные):
5,6-DISUBSTITUTED BENZIMIDAZOLES -- NUCLEOSIDES -- PURINE NUCLEOSIDE PHOSPHORYLASE
Аннотация: A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic- bases showed good substrate activity for PNP and the ribo- and 2′-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-D-ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-D-ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2-deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cy

\\\\expert2\\nbo\\Synthesis\\2013, v. 45. N 2. p. 272-280.pdf
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10.
Инвентарный номер: нет.
   
   N 89

   
    Novel purine conjugates with N-heterocycles: synthesis and anti-influenza activity / V. P. Krasnov, V. V. Zarubaev, D. V. Gruzdev [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P498-504
УДК
Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
6-CHLOROPURINE -- HETEROCYCLIC AMINES -- ANTIVIRAL ACTIVITY -- INFLUENZA A AND B VIRUSES
Аннотация: A number of novel amides were synthesized by coupling of 6-[(9H-purin-6-yl)amino]hexanoic acid to heterocyclic amines. The antiviral activity of the obtained compounds, as well as of purine conjugates in which 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine is linked to position 6 of purine through a fragment of ɷ-amino acids with varying lengths of polymethylene chains against influenza A and B viruses was studied in vitro. Purine derivatives have been shown to have moderate activity against influenza A (H1N1) virus. The antiinfluenza activity and cytotoxicity of conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine depend on the length of the linker fragment.

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