Synthesis of (1S)-(+)-camphor-10-sulfonic acid derivatives and investigations in vitro and in silico of their antiviral activity as the inhibitors of fi lovirus infections

Соколова, А. С.; Baranova, Daria; Yarovaya, Оlga I.; Baev, Dmitry S.; Полежаева, О. А.; Zybkina, Anastasiya V.; Щербаков, Д. Н.; Толстикова, Т. Г.; Salakhutdinov, N. F.

doi:10.1007/s11172-019-2517-0

Cited by 21 publications

(8 citation statements)

References 17 publications

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“…All IC 50 values are given in μM. Anti-influenza activity is described in [ 16 ], anti-orthopoxvirus—[ 14 , 17 ], anti-filovirus—[ 10 , 11 , 12 ].…”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

“…Many different classes of camphor-based derivatives have been synthesized with a wide range of antiviral properties. We have previously shown that derivatives with a 1,7,7-trimethylbicyclo[2.2.1]heptane backbone exhibit a wide spectrum of antiviral activity against influenza [ 7 , 8 ], hantaviruses [ 9 ], filoviruses [ 10 , 11 , 12 ], orthopoxviruses [ 13 , 14 ] and SARS-CoV-2 [ 15 ]. Some compounds, with a heterocyclic fragment synthesized previously on the basis of camphor and borneol, which have shown significant antiviral properties, are presented in Figure 1 .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antiviral Properties of Camphor-Derived Iminothiazolidine-4-Ones and 2,3-Dihydrothiazoles

Oreshko

Kovaleva²,

Mordvinova³

et al. 2022

Molecules

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A set of heterocyclic products was synthesized from natural (+)-camphor and semi-synthetic (−)-camphor. Then, 2-Imino-4-thiazolidinones and 2,3-dihydrothiazoles were obtained using a three-step procedure. For the synthesized compounds, their antiviral activity against the vaccinia virus and Marburg virus was studied. New promising agents active against both viruses were found among the tested compounds.

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“…All IC 50 values are given in μM. Anti-influenza activity is described in [ 16 ], anti-orthopoxvirus—[ 14 , 17 ], anti-filovirus—[ 10 , 11 , 12 ].…”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiviral Properties of Camphor-Derived Iminothiazolidine-4-Ones and 2,3-Dihydrothiazoles

Oreshko

Kovaleva²,

Mordvinova³

et al. 2022

Molecules

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“…Another example, where the (1 S )-(+)-camphor-10-sulfonic acid was used as a precursor of N -heterocycle compounds, is the work where compounds from the group of (1 S )-(+)-camphor-10-sulfonamide derivatives 129 ( Figure 33 ) were investigated as antiviral inhibitors against filoviruses [ 102 ]. The derivatives bearing morpholine 129a and triazole 129g moieties exhibit the highest inhibitory activity towards the Ebola virus glycoprotein, with the effectiveness level comparable to that of the reference drug.…”

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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“…The compounds that were produced by MCRs method are desirable for medicinal and synthetic chemists [10][11][12][13][14][15]. In medicinal chemistry, compounds with one or more of heteroatom have an important position because of their broad field of biological properties [16][17][18][19][20][21][22][23][24]. Furthermore, the heterocyclic compounds have main role in the field of much science such as material [25], dyes and pigment [26] and agrochemistry [27].…”

Section: Introductionmentioning

confidence: 99%

Employing of Fe3O4/CuO/ZnO@MWCNT MNCs in the solvent-free synthesis of new cyanopyrroloazepine derivatives and investigation of biological activity

et al. 2021

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In this research, we synthesized the Fe 3 O 4 /CuO/ZnO@MWCNT magnetic nanocomposites using water extract of Petasites hybridus rhizome, and the high performance of synthesized catalyst was confirmed by using in the solvent-free multicomponent reactions of isatoic anhydride, N-methylimidazole, alkyl bromides, activated acetylenic compounds and 2-aminoacetonitrile at ambient temperature for the production of new cyanopyrroloazepine derivatives in high yields. This catalyst could be used several times in these reactions and have main role in the yield of product. The synthesized cyanopyrroloazepines have NH groups in their structure and for this reason have good antioxidant activity. Also, employing Gram-positive and Gram-negative bacteria in the disk diffusion procedure confirmed some cyanopyrroloazepines antimicrobial effect. The results showed that synthesized cyanopyrroloazepine prevented the bacterial growth. This used process for preparation of new cyanopyrroloazepine has some improvements such as low reaction time, product with high yields, simple separation of catalyst and products.

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Synthesis of (1S)-(+)-camphor-10-sulfonic acid derivatives and investigations in vitro and in silico of their antiviral activity as the inhibitors of fi lovirus infections

Cited by 21 publications

References 17 publications

Synthesis and Antiviral Properties of Camphor-Derived Iminothiazolidine-4-Ones and 2,3-Dihydrothiazoles

Synthesis and Antiviral Properties of Camphor-Derived Iminothiazolidine-4-Ones and 2,3-Dihydrothiazoles

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

Employing of Fe3O4/CuO/ZnO@MWCNT MNCs in the solvent-free synthesis of new cyanopyrroloazepine derivatives and investigation of biological activity

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