Azepanodipterocarpol is potential candidate for inhibits influenza H1N1 type among other lupane, oleanane, and dammarane A-ring amino-triterpenoids

Смирнова, И. Е.; Petrova, А. V.; Лобов, А. Н.; Minnibaeva, E. M.; Phuong, Thao Tran Thi; Van, Loc Tran; Khine, Myint Myint; Есаулкова, Яна Л.; Slita, Alexander V.; Zarubaev, Vladimir V.; Казакова, О. Б.

doi:10.1038/s41429-022-00514-w

Cited by 8 publications

(3 citation statements)

References 43 publications

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“…Thus, gomopiperazine amide 2 with IC 50 of 21 µM and SI > 27 was established as the most active compound in this series, which is consistent with the data, demonstrating that triterpenoids derivatives with cyclic amide moieties had the highest antiviral activity [ 46 ]. Previously, we have found that methyl 3 β -amino-oleanoate 21 has antiviral activity with an IC 50 of 7.9 μM, but a higher CC 50 of 18 μM which led to lowering the selectivity index (SI 2) [ 47 ]. The esterification of methyl 3 β -amino-oleanoate 21 with phthalic anhydride resulted increased activity (IC 50 of 12 μM), but significantly lower toxicity (CC 50 > 486 μM) in compound 22 , resulting in a selectivity index of >42.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

et al. 2022

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A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50′s 67 and 107 μM) and -2 (IC50′s 86 and 68 μM correspondingly) serotypes.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

et al. 2022

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“…Their activity toward a broad spectrum of viruses is known, including herpes, papilloma, human immunodeficiency, hepatitis, influenza viruses, SARS‐CoV‐2, cytomegalovirus, etc. (Babaev et al., 2022; Kazakova, Tret'yakova, & Baev, 2021; Liu, Yang, Wang & Xiong, 2022; Smirnova et al., 2022; Wu et al., 2020; Ye et al., 2021; Yi et al., 2022). The antiviral effect of these compounds is due to several types of activity including direct antiviral action, effects on cellular antiviral pathways, and immunomodulatory activity, in particular, activation of the nonspecific immunity system (Li, Sun, Xiao, Zhang & Zhou, 2020; Xiao et al., 2018).…”

Section: Introductionmentioning

confidence: 99%

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Petrova,

Tretyakova,

Khusnutdinova

et al. 2023

Chem Biol Drug Des

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Oleanolic and glycyrrhetic acids alkyne derivatives were synthesized as a result of propargylation of the indole NH‐group condensed with the triterpene A‐ring, the following aminomethylation led to a series of Mannich bases. The synthesized compounds were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in Madin‐Darby canine kidney (MDCK) cell culture and SARS‐CoV‐2 pseudovirus in baby hamster kidney‐21‐human angiotensin‐converting enzyme 2 (BHK‐21‐hACE2) cells. Mannich bases of oleanolic and glycyrrhetic acids N‐propargylated indoles 7, 8, and 12 were the most efficacious against influenza virus A with IC50 7–10 μM together with a low toxicity (CC50 > 145 μM) and high selectivity index SI value 20. Indolo‐oleanolic acid morpholine amide Mannich base holding N‐methylpiperazine moiety 9 showed anti‐SARS‐CoV‐2 pseudovirus activity with EC50 value of 14.8 μM. Molecular docking and dynamics modeling investigated the binding mode of the compounds 7 and 12 into the binding pocket of influenza A virus M2 protein and compound 9 into the RBD domain of SARS‐CoV‐2 spike glycoprotein.

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“…Data on the synthesis conditions and properties of the obtained polymers are summarized in Table 1. The cytotoxic and antiviral properties of polymers were evaluated in vitro as described in [10].…”

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confidence: 99%

Synthesis and Anti-influenza Activity of Vinylphosphonic Acid (Co)polymers

Zarubaev

Buchkov²,

Назарова³

et al. 2022

Dokl Biochem Biophys

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New copolymers of vinylphosphonic acid (VPA) with 2-deoxy-2-methacrylamido-D-glucose, 4-acryloylmorpholine (4-AM), and acrylamide have been synthesized, and their antiviral activity against influenza virus has been studied in in vitro and in vivo experiments. Optimal antiviral characteristics and low cytotoxicity were exhibited by the copolymer of VPA with 4-AM, composition 56 : 44 mol %, molecular weight 33000. The polymer exhibited virus-inhibiting properties with an IC 50 = 1 μg/mL and a selectivity index of 302. Prophylactic intranasal administration of the polymer in a murine model of influenza pneumonia completely prevented the virus-induced death of animals, whereas the level of mortality in the placebo group was 90%. The results of this study indicate a high antiviral potential of polymeric compounds based on VPA.

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Azepanodipterocarpol is potential candidate for inhibits influenza H1N1 type among other lupane, oleanane, and dammarane A-ring amino-triterpenoids

Cited by 8 publications

References 43 publications

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Synthesis and Anti-influenza Activity of Vinylphosphonic Acid (Co)polymers

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