Synthesis and biological activity of heterocyclic borneol derivatives

Соколова, А. С.; Yarovaya, Оlga I.; Штро, Анна А.; Borisova, Marina S.; Морозова, Е. А.; Толстикова, Т. Г.; Zarubaev, Vladimir V.; Salakhutdinov, N. F.

doi:10.1007/s10593-017-2063-3

Cited by 25 publications

(15 citation statements)

References 14 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%

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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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“…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%

“…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%

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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“…In China’s and India’s traditional medicine, borneol has long since been used as a remedy against gastrointestinal diseases. (–)-Borneol and its derivatives are antimicrobial [ 103 ], anti-inflammatory [ 104 ], and antiviral [ 105 ]. Borneol has been shown to promote drugs crossing through the blood–brain barrier, thus improving the efficiency of these drugs [ 106 ].…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

“…One of the works on this subject is an article studying various heterocyclic (–)-borneol derivatives with benzothiazole, benzoxazole, benzimidazole, and other heterocycles moieties ( Figure 38 ) [ 105 ]. Those compounds were analyzed due to their biological properties, including their possible use as antiviral, antiulcer, and analgesic agents.…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Zielińska-Błajet

Feder‐Kubis

2020

IJMS

190

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Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

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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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Synthesis and biological activity of heterocyclic borneol derivatives

Cited by 25 publications

References 14 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

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

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

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