Synthesis of New Compounds Combining Adamantanamine and Monoterpene Fragments and their Antiviral Activity Against Influenza Virus A(H1N1)pdm09

Teplov, George V.; Суслов, Е. В.; Zarubaev, Vladimir V.; Штро, Анна А.; Karpinskaya, L. A.; Rogachev, Artem D.; Корчагина, Д. В.; Волчо, К. П.; Salakhutdinov, N. F.; Киселев, О. И.

doi:10.2174/1570180811310060002

Cited by 25 publications

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“… 16 Here, we screened over 170 natural derivatives in a Marburg glycoprotein-mediated VSIV pseudotype system. The library of natural compounds includes the derivatives of (+)-camphor, 17 , 18 (–)-borneol, 19 , 20 dehydroabietylamine, 21 , 22 para -mentha-1,8-dien-5,6-diol, 23 – 26 (–)-isopulegol, 27 deoxycholic acid, 28 (+)-usninic acid, 29 aminoadamantane 30 , 31 and azaadamantane 32 which were previously described by our colleagues. Among the tested derivatives, the bornyl ester containing saturated N-heterocycles exhibited the highest antiviral activity with several hit compounds identified.…”

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confidence: 99%

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

et al. 2017

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confidence: 99%

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

et al. 2017

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“…Compound 72 was tested in vitro for antiviral activity against the influenza virus A/California/07/09 (H1N1)pdm09. The results indicated that the introduction of a myrtenal fragment led to an increase in the antiviral activity of adamantylamine derivatives against the adamantylamine resistant virus: The selectivity index of the majority of the synthesized amines was higher than that of rimantadine and amantadine [ 68 ]. Compound 73 was synthesized from 1-aminoadamantane and (–)-myrtenal and its cytotoxic activity against human cancer cells CEM-13, MT-4, and U-937 was studied.…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

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

Zielińska-Błajet

Feder‐Kubis

2020

IJMS

184

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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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“…In addition, synthesis of vitamins, insecticides, and pharmaceuticals also starts from terpenes [33][34][35][36][37]. Acyclic terpene amines are of special interest for production of insecticides, fungicides, and herbicides as well as in development of new pharmaceuticals [38][39][40][41][42][43]. Amino terpenes on the basis of (−)-menthol and (+)-3-carene were used for the preparation of potential inhibitors of γ-aminobutyric acid neuro-receptors for neurological applications [44,45].…”

Section: Terpenes Valorization Into Valuable Aminesmentioning

confidence: 99%

Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

2018

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This review fills an apparent gap existing in the literature by providing an overview of the readily available terpenes and existing catalytic protocols for preparation of terpene-derived amines. To address the role of solid catalysts in amination of terpenes the same reactions with homogeneous counterparts are also discussed. Such catalysts can be considered as a benchmark, which solid catalysts should match. Although catalytic systems based on transition metal complexes have been developed for synthesis of amines to a larger extent, there is an apparent need to reduce the production costs. Subsequently, homogenous systems based on cheaper metals operating by nucleophilic substitution (e.g., Ni, Co, Cu, Fe) with a possibility of easy recycling, as well as metal nanoparticles (e.g., Pd, Au) supported on amphoteric oxides should be developed. These catalysts will allow synthesis of amine derivatives of terpenes which have a broad range of applications as specialty chemicals (e.g., pesticides, surfactants, etc.) and pharmaceuticals. The review will be useful in selection and design of appropriate solid materials with tailored properties as efficient catalysts for amination of terpenes.

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Synthesis of New Compounds Combining Adamantanamine and Monoterpene Fragments and their Antiviral Activity Against Influenza Virus A(H1N1)pdm09

Cited by 25 publications

References 0 publications

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

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

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

Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

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