Synthesis and antiviral activity of maleopimaric and quinopimaric acids’ derivatives

Tret’yakova, E. V.; Смирнова, И. Е.; Салимова, Е. В.; Odinokov, V. N.

doi:10.1016/j.bmc.2015.09.006

Cited by 44 publications

(13 citation statements)

References 34 publications

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“…Using the RP HPLC method it has been shown that the cone-shaped calix [4]arene and calix [4]resorcinarene functionalized at the upper rim with proton accepting imino groups or phosphoryl groups, respectively, form strong Host-Guest inclusion complexes (K A 395-1268 M -1 ) with a series of diterpenoid (resin) acids in water-containing solutions. The complexes are stabilized by the hydrophobic Host-Guest interactions and hydrogen bonds of the Guest COOH groups with basic nitrogen atoms or oxygen atoms of the Host molecule.…”

Section: Discussionmentioning

confidence: 99%

“…Formerly it was shown that octakis(diphenoxyphosphoryloxy)calix [4]resorcinarene (Cr) and bisiminocalix [4]arene (CA) appeared to be effective complexing agents for aromatic hydrocarbons [23], benzene carboxylic acids [24,25], pyridine carboxylic acids [26] and 2,4-dichlorophenoxyacetic acid [27].…”

Section: ре-зорцинарену (Cr) та 517-біс-(n-толілімінометил)-2527-диmentioning

confidence: 99%

“…1. Structural formulas of calix [4]resorcinarene CR, calix [4]arene CA (Hosts) and pimaric 1, maleopimaric 2, palustric 3, dehydroabietic 4, abietic 5, neoabietic 6 acids (Guest).…”

Section: ре-зорцинарену (Cr) та 517-біс-(n-толілімінометил)-2527-диmentioning

confidence: 99%

“…арени; смоляні кислоти; обернено-фазна високоефективна рідинна хромато-графія; комплекси включення; константи зв'язування; молекулярне моделювання Комплексоутворення типу Гість-Господар oктакіс-(дифеноксифосфорилокси)-тетраметилкалікс [4] Naturally occurring di-and triterpenoid acids are isolated from different plant sources [1], have a wide variety of biological activities [2][3][4][5][6][7][8][9], and generate considerable interest in the pharmacological community. These compounds play an important role in searching new drugs for the treatment of different diseases.…”

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The study of the Complexation of Calix[4]arene and Calix[4]resorcinarene with resin acids by the RP HPLC method. binding constants determination

Kalchenko

Cherenok

Solovyov

et al. 2016

J. org. pharm. chem.

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Section: Discussionmentioning

confidence: 99%

Section: ре-зорцинарену (Cr) та 517-біс-(n-толілімінометил)-2527-диmentioning

confidence: 99%

“…1. Structural formulas of calix [4]resorcinarene CR, calix [4]arene CA (Hosts) and pimaric 1, maleopimaric 2, palustric 3, dehydroabietic 4, abietic 5, neoabietic 6 acids (Guest).…”

Section: ре-зорцинарену (Cr) та 517-біс-(n-толілімінометил)-2527-диmentioning

confidence: 99%

unclassified

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The study of the Complexation of Calix[4]arene and Calix[4]resorcinarene with resin acids by the RP HPLC method. binding constants determination

Kalchenko

Cherenok

Solovyov

et al. 2016

J. org. pharm. chem.

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“…The mechanism of action of these drugs is associated with the formation of acyl-enzyme derivatives. It's based on the blocking of one of the three areas that are critical to the activity of aspartic proteases of the virus: the catalytic core of the enzyme, containing the pair of Asp-Thr/Ser-Gly triad; mobile flap-domain and dimerization domain on the N-and C-termini of the protease [27,28].…”

Section: Expression Of Viral Genomes and Assembly Of New Viral Particlesmentioning

confidence: 99%

Levels of Antiviral Therapy

Ap¹,

Turmagambetova²,

Berezin³

2016

JHVRV

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Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS‐CoV‐2 Spike Glycoprotein and Influenza A Virus

Tretyakova,

Hua,

Smirnova

et al. 2024

Asian J Org Chem

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Abietane type diterpenic (dehydroabietic, 2,3‐dihydroquinopimaric and maleopimaric) acids were converted by the acid chloride method into a series of aliphatic and heterocyclic amine spacered conjugates. A number of structurally novel derivatives holding 1,2,3‐triazole moieties were designed and synthesized by treating of the propargylated amides and esters with a sugar azides using the Cu(I)‐catalyzed click chemistry approach. The synthesized N‐containing diterpene derivatives were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in MDCK cell culture and SARS‐CoV‐2 pseudovirus in BHK‐21‐hACE2 cells. Among tested forty‐five compounds ten derivatives were the most efficacious against influenza virus A with IC50 0.7–63.4 μM together with high selectivity index SI value from 11 from 94. Dihydroquinopimaric acid N‐ethylpiperazine‐amide and dehydroabietic acid 1,2,3‐triazoles spacered with glucose and lactose showed anti‐SARS‐CoV‐2 pseudovirus activity with EC50 values of 1.79–25.46 μM. Molecular docking and dynamics modeling investigated the binding mode of the lead compounds into the binding pocket of influenza A virus M2 protein and the RBD domain of SARS‐CoV‐2 spike glycoprotein.

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Synthesis and antiviral activity of maleopimaric and quinopimaric acids’ derivatives

Cited by 44 publications

References 34 publications

The study of the Complexation of Calix[4]arene and Calix[4]resorcinarene with resin acids by the RP HPLC method. binding constants determination

The study of the Complexation of Calix[4]arene and Calix[4]resorcinarene with resin acids by the RP HPLC method. binding constants determination

Levels of Antiviral Therapy

Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS‐CoV‐2 Spike Glycoprotein and Influenza A Virus

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