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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Published inMolecules (Basel, Switzerland) Vol. 27; no. 23; p. 8499
Main Authors 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
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.12.2022
MDPI
Subjects
Amides
Amides - therapeutic use
Amines
Antimicrobial agents
Antiviral activity
Antiviral agents
Antiviral Agents - therapeutic use
benzylidene
Cancer
Cell cycle
Cytotoxicity
Dengue
Dengue fever
E coli
Herbal medicine
Humans
indole
Influenza
Influenza A
Influenza A Virus, H1N1 Subtype
Influenza, Human - drug therapy
Methicillin
oleanolic acid
polyamine
Polyamines
Polyamines - pharmacology
Polyamines - therapeutic use
Selectivity
Serotypes
Severe acute respiratory syndrome coronavirus 2
Triterpenes - therapeutic use
triterpenoids
Ugi derivatives
Vector-borne diseases
Viruses
China
polyamine
influenza A (H1N1)
indole
Ugi derivatives
oleanolic acid
triterpenoids
antiviral activity
Dengue virus
benzylidene
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Summary: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 and 3- -phthalyl amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC 21 μM) and 42 (IC 12 μM). Oleanonic acid aminoethylpiperazine amide and C-azepano-erythrodiol appeared to be the most effective compounds against DENV-1 (IC s 67 and 107 μM) and -2 (IC s 86 and 68 μM correspondingly) serotypes.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27238499