Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus

Соколова, А. С.; Yarovaya, Оlga I.; Semenova, Marya D.; Штро, Анна А.; Orshanskaya, Iana R.; Zarubaev, Vladimir V.; Salakhutdinov, N. F.

doi:10.1039/c6md00657d

Cited by 50 publications

(35 citation statements)

References 22 publications

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“…Previously, we described the synthesis of several compounds according to the references 1 , 2 , 8 , 9 , 11 , 13 , 14 , 16 – 18 , 20 , 22 – 25 and 4 – 7 …”

Section: Methodsmentioning

confidence: 99%

“…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%

“…[10] [11] Of the borneol derivatives, N-heterocyclic bornyl esters demonstrated high antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1). [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: 97%

“…Of the camphor derivatives synthesized, imines showed promising activity against the influenza virus. [ ][ ] 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 .…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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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“…Previously, we described the synthesis of several compounds according to the references 1 , 2 , 8 , 9 , 11 , 13 , 14 , 16 – 18 , 20 , 22 – 25 and 4 – 7 …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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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“…[1] For example, the introduction of pharmacophoric groups into camphor [2,3] and fenchone [4] molecules leads to formation of compounds showing antituberculous activity. Oxygen-containing monoterpenes proved to be efficient against influenza virus [5,6] and Marburg virus. [7] 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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(+)‐Camphor and (−)‐borneol derivatives as potential anti‐orthopoxvirus agents

Соколова

Kovaleva

Yarovaya

et al. 2021

Archiv der Pharmazie

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Although the World Health Organisation had announced that smallpox was eradicated over 40 years ago, the disease and other related pathogenic poxviruses such as monkeypox remain potential bioterrorist weapons and could also re-emerge as natural infections. We have previously reported (+)-camphor and (−)-borneol derivatives with an antiviral activity against the vaccinia virus. This virus is similar to the variola virus (VARV), the causative agent of smallpox, but can be studied at BSL-2 facilities. In the present study, we evaluated the antiviral activity of the most potent compounds against VARV, cowpox virus, and ectromelia virus (ECTV). Among the compounds tested, 4-bromo-Nʹ-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2ylidene)benzohydrazide 18 is the most effective compound against various orthopoxviruses, including VARV, with an EC 50 value of 13.9 μM and a selectivity index of 206. Also, (+)-camphor thiosemicarbazone 9 was found to be active against VARV and ECTV.

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Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus

Abstract: Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (–)-borneol and (–)-isoborneol as potent inhibitors of the influenza A virus.

Cited by 50 publications

References 22 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

(+)‐Camphor and (−)‐borneol derivatives as potential anti‐orthopoxvirus agents

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