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

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 serotype...

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Autores principales: Smirnova, Irina, Petrova, Anastasiya, Giniyatullina, Gul’nara, Smirnova, Anna, Volobueva, Alexandrina, Pavlyukova, Julia, Zarubaev, Vladimir, Loc, Tran Van, Tran Thi Phoung, Thao, Hau, Vu Thi Bich, Thuy, Nguyen Thi Thu, Khine, Myint Myint, Kazakova, Oxana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738632/
https://www.ncbi.nlm.nih.gov/pubmed/36500593
http://dx.doi.org/10.3390/molecules27238499
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author Smirnova, Irina
Petrova, Anastasiya
Giniyatullina, Gul’nara
Smirnova, Anna
Volobueva, Alexandrina
Pavlyukova, Julia
Zarubaev, Vladimir
Loc, Tran Van
Tran Thi Phoung, Thao
Hau, Vu Thi Bich
Thuy, Nguyen Thi Thu
Khine, Myint Myint
Kazakova, Oxana
author_facet Smirnova, Irina
Petrova, Anastasiya
Giniyatullina, Gul’nara
Smirnova, Anna
Volobueva, Alexandrina
Pavlyukova, Julia
Zarubaev, Vladimir
Loc, Tran Van
Tran Thi Phoung, Thao
Hau, Vu Thi Bich
Thuy, Nguyen Thi Thu
Khine, Myint Myint
Kazakova, Oxana
author_sort Smirnova, Irina
collection PubMed
description 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 (IC(50) 21 μM) and 42 (IC(50) 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC(50′)s 67 and 107 μM) and -2 (IC(50′)s 86 and 68 μM correspondingly) serotypes.
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spelling pubmed-97386322022-12-11 Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives Smirnova, Irina Petrova, Anastasiya Giniyatullina, Gul’nara Smirnova, Anna Volobueva, Alexandrina Pavlyukova, Julia Zarubaev, Vladimir Loc, Tran Van Tran Thi Phoung, Thao Hau, Vu Thi Bich Thuy, Nguyen Thi Thu Khine, Myint Myint Kazakova, Oxana Molecules Article 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 (IC(50) 21 μM) and 42 (IC(50) 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC(50′)s 67 and 107 μM) and -2 (IC(50′)s 86 and 68 μM correspondingly) serotypes. MDPI 2022-12-02 /pmc/articles/PMC9738632/ /pubmed/36500593 http://dx.doi.org/10.3390/molecules27238499 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Smirnova, Irina
Petrova, Anastasiya
Giniyatullina, Gul’nara
Smirnova, Anna
Volobueva, Alexandrina
Pavlyukova, Julia
Zarubaev, Vladimir
Loc, Tran Van
Tran Thi Phoung, Thao
Hau, Vu Thi Bich
Thuy, Nguyen Thi Thu
Khine, Myint Myint
Kazakova, Oxana
Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
title Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
title_full Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
title_fullStr Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
title_full_unstemmed Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
title_short Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives
title_sort synthesis, anti-influenza h1n1 and anti-dengue activity of a-ring modified oleanonic acid polyamine derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738632/
https://www.ncbi.nlm.nih.gov/pubmed/36500593
http://dx.doi.org/10.3390/molecules27238499
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