N-Heterocyclic borneol derivatives as inhibitors of Marburg virus glycoprotein-mediated VSIV pseudotype entry

Kononova, A. A.; Соколова, А. С.; Чересиз, С. В.; Yarovaya, Оlga I.; Nikitina, Raisa A.; Chepurnov, A. A.; Pokrovsky, Andrey G.; Salakhutdinov, N. F.

doi:10.1039/c7md00424a

Cited by 29 publications

(26 citation statements)

References 35 publications

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“…1 H-and 13 C-NMR spectra were recorded on Bruker AV-300 ( 1 H: 300. 13 MHz, 13 C: 75.47 MHz), AV-400 Previously, we described the synthesis of several compounds according to the references 1, 2, 8, 9, 11, 13, 14, 16 -18, 20, 22 -25 [12] and 4 -7. [16] Synthesis of (1S,2R,4S)-1,7,7-Trimethylbicyclo…”

Section: Methodsmentioning

confidence: 99%

“…[ ][ ] Of the borneol derivatives, N‐heterocyclic bornyl esters demonstrated high antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) . Moreover, we have shown that some bornyl esters are able to specifically inhibit Marburg virus entry into the target cell . Thus, the 1,7,7‐trimethylbicyclo[2.2.1]heptane scaffold is an important pharmacophore for exhibiting high inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

“…[12] Moreover, we have shown that some bornyl esters are able to specifically inhibit Marburg virus entry into the target cell. [13] Thus, the 1,7,7-trimethylbicyclo[2.2.1]heptane scaffold is an important pharmacophore for exhibiting high inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

“…J(1 exo ,2 endo ) = 3.5, J(1 exo ,5 exo ) = 2.2, H-1 exo ) 13. C-NMR: 173.67 (s, C-11), 79.59 (d, C-1), 57.55 (t, C-14), 54.96 (t, C-16, C-18), 52.98 (t, C-15, C-17), 48.59 (s, C-6), 47.63 (s, C-7), 45.91 (q, Me-19), 44.71 (d, C-3), 36.68 (t, C-2), 32.47 (t, C-12), 27.90 (t, C-4), 26.97 (t, C-5), 22.15 (t, C-13), 19.56 (q, Me-9), 18.69 (q, Me-10), 13.41 (q, Me-8).…”

mentioning

confidence: 96%

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Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor

Соколова

Yarovaya

Бормотов

et al. 2018

Chemistry & Biodiversity

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A series of the bornyl ester/amide derivatives with N-containing heterocycles were designed and synthesized as vaccinia virus (VV) inhibitors. Bioassay results showed that among the designed compounds, derivatives 6, 13, 14, 34, 36 and 37 showed the best inhibitory activity against VV with the IC values of 12.9, 17.9, 3.4, 2.5, 12.5 and 7.5 μm, respectively, and good cytotoxicity. The primary structure-activity relationship (SAR) study suggested that the combination of a saturated N-heterocycle, such as morpholine or 4-methylpiperidine, and a 1,7,7-trimethylbicyclo[2.2.1]heptane scaffold was favorable for antiviral activity.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 96%

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Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor

Соколова

Yarovaya

Бормотов

et al. 2018

Chemistry & Biodiversity

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“…For example, the introduction of pharmacophoric groups into camphor and fenchone molecules leads to formation of compounds showing antituberculous activity. Oxygen‐containing monoterpenes proved to be efficient against influenza virus and Marburg virus . Although the 1,2,3‐triazole moiety does not exist in nature, it has attracted interest as a candidate anticancer drug, particularly for the production of ‘1,2,3‐triazole‐natural compound’ hybrids .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Camphecene and Cytisine Conjugates Using Click Chemistry Methodology and Study of Their Antiviral Activity

Аrtyushin

Moiseeva

Zarubaev

et al. 2019

Chemistry & Biodiversity

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A series of camphecene and quinolizidine alkaloid (−)‐cytisine conjugates has been obtained for the first time using ‘click’ chemistry methodology. The cytotoxicity and virus‐inhibiting activity of compounds were determined against MDCK cells and influenza virus A/Puerto Rico/8/34 (H1N1), correspondingly, in in vitro tests. Based on the results obtained, values of 50 % cytotoxic dose (CC50), 50 % inhibition dose (IC50) and selectivity index (SI) were determined for each compound. It has been shown that the antiviral activity is affected by the length and nature of linkers between cytisine and camphor units. Conjugate 13 ((1R,5S)‐3‐(6‐{4‐[(2‐{(E)‐[(1R,4R)‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐ylidene]amino}ethoxy)methyl]‐1H‐1,2,3‐triazol‐1‐yl}hexyl)‐1,2,3,4,5,6‐hexahydro‐8H‐1,5‐methanopyrido[1,2‐a][1,5]diazocin‐8‐one), which contains cytisine fragment separated from triazole ring by –C6H12– aliphatic linker, showed the highest activity at relatively low toxicity (CC50=168 μmol, IC50=8 μmol, SI=20). Its selectivity index appeared higher than that of reference compound, rimantadine. According to theoretical calculations, the antiviral activity of the lead compound 13 can be explained by its influence on the functioning of neuraminidase.

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Quaternary ammonium salts based on (-)-borneol as effective inhibitors of influenza virus

et al. 2021

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A series of compounds containing a 1,7,7-trimethylbicyclo[2.2.1]heptane fragment were evaluated for their antiviral activity against influenza A virus strain A/Puerto Rico/8/34 (H1N1) in vitro . The most potent antiviral compound proved to be a quaternary ammonium salt based on (-)-borneol, 10a. In in vitro experiments, compound 10a inhibited influenza A viruses (H1, H1pdm09, and H3 subtypes), with an IC 50 value of 2.4-16.8 µM (depending on the virus), and demonstrated low toxicity (CC 50 = 1311 µM). Mechanism-of-action studies for compound 10a revealed it to be most effective when added at the early stages of the viral life cycle. In direct haemolysis inhibition tests, compound 10a was shown to decrease the membrane-disrupting activity of influenza A virus strain A/Puerto Rico/8/34. According to molecular modelling results, the lead compound 10a can bind to different sites in the stem region of the viral hemagglutinin. Supplementary Information The online version contains supplementary material available at 10.1007/s00705-021-05102-1.

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N-Heterocyclic borneol derivatives as inhibitors of Marburg virus glycoprotein-mediated VSIV pseudotype entry

Abstract: Screening of a library of natural derivatives for their virus entry inhibition activity using pseudotype systems shows bornyl ester derivatives containing saturated N-heterocycles exhibiting the highest antiviral activity.

Cited by 29 publications

References 35 publications

Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor

Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor

Synthesis of Camphecene and Cytisine Conjugates Using Click Chemistry Methodology and Study of Their Antiviral Activity

Quaternary ammonium salts based on (-)-borneol as effective inhibitors of influenza virus

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