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Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.

Identifieur interne : 000E34 ( PubMed/Curation ); précédent : 000E33; suivant : 000E35

Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.

Auteurs : Sheng Liu [République populaire de Chine] ; Wanxing Wei [République populaire de Chine] ; Yubin Li [République populaire de Chine] ; Xu Liu [République populaire de Chine] ; Xiaoji Cao [République populaire de Chine] ; Kechan Lei [République populaire de Chine] ; Min Zhou [République populaire de Chine]

Source :

European journal of medicinal chemistry [ 1768-3254 ] ; 2015.

RBID : pubmed:25847765

Descripteurs français

English descriptors

KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (metabolism), Antiviral Agents (pharmacology), Catalytic Domain, Chemistry Techniques, Synthetic, DNA Replication (drug effects), Drug Design, HLA-A Antigens (chemistry), HLA-A Antigens (metabolism), Hep G2 Cells, Hepatitis B Surface Antigens (metabolism), Hepatitis B e Antigens (metabolism), Hepatitis B virus (drug effects), Hepatitis B virus (metabolism), Hepatitis B virus (physiology), Humans, Molecular Docking Simulation, Phenols (chemical synthesis), Phenols (chemistry), Phenols (metabolism), Phenols (pharmacology), Quantitative Structure-Activity Relationship, Virus Replication (drug effects).
MESH :
- chemical , chemical synthesis : Antiviral Agents, Phenols.
- chemical , chemistry : Antiviral Agents, HLA-A Antigens, Phenols.
- chemical , metabolism : Antiviral Agents, HLA-A Antigens, Hepatitis B Surface Antigens, Hepatitis B e Antigens, Phenols.
- chemical , pharmacology : Antiviral Agents, Phenols.
- drug effects : DNA Replication, Hepatitis B virus, Virus Replication.
- metabolism : Hepatitis B virus.
- physiology : Hepatitis B virus.
- Catalytic Domain, Chemistry Techniques, Synthetic, Drug Design, Hep G2 Cells, Humans, Molecular Docking Simulation, Quantitative Structure-Activity Relationship.

Abstract

A series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the synthesized derivatives showed effective anti-HBV activity. Of these compounds, compound 4c-1 showed the most potent anti-HBV activity, demonstrating potent inhibitory effect not only on the secretion of HBsAg (IC50 = 14.18 μM, SI = 17.85) and HBeAg (IC50 = 6.20 μM, SI = 40.82) secretion but also HBV DNA replication (IC50 = 23.43 μM, SI = 10.80). The structure-activity relationships (SARs) of phenylpropanoid derivatives had been discussed, which were useful for phenylpropanoid derivatives to be explored and developed as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site were carried out to explore the molecular interactions and a molecular target for activity of phenylpropanoid derivatives with the protein using a moe-docking technique. This study identified a new class of potent anti-HBV agents.

DOI: 10.1016/j.ejmech.2015.03.056
PubMed: 25847765

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<front><div type="abstract" xml:lang="en">A series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the synthesized derivatives showed effective anti-HBV activity. Of these compounds, compound 4c-1 showed the most potent anti-HBV activity, demonstrating potent inhibitory effect not only on the secretion of HBsAg (IC50 = 14.18 μM, SI = 17.85) and HBeAg (IC50 = 6.20 μM, SI = 40.82) secretion but also HBV DNA replication (IC50 = 23.43 μM, SI = 10.80). The structure-activity relationships (SARs) of phenylpropanoid derivatives had been discussed, which were useful for phenylpropanoid derivatives to be explored and developed as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site were carried out to explore the molecular interactions and a molecular target for activity of phenylpropanoid derivatives with the protein using a moe-docking technique. This study identified a new class of potent anti-HBV agents. </div>
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<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Anti-HBV activity</Keyword>
<Keyword MajorTopicYN="N">Molecular docking</Keyword>
<Keyword MajorTopicYN="N">Phenylpropanoid derivatives</Keyword>
<Keyword MajorTopicYN="N">Structure–activity relationships</Keyword>
<Keyword MajorTopicYN="N">Synthesis</Keyword>
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<PubMedPubDate PubStatus="revised"><Year>2015</Year>
<Month>03</Month>
<Day>24</Day>
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<PubMedPubDate PubStatus="accepted"><Year>2015</Year>
<Month>03</Month>
<Day>25</Day>
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<ArticleIdList><ArticleId IdType="pubmed">25847765</ArticleId>
<ArticleId IdType="pii">S0223-5234(15)00223-8</ArticleId>
<ArticleId IdType="doi">10.1016/j.ejmech.2015.03.056</ArticleId>
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Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.

Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.

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