Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
Identifieur interne : 001291 ( Main/Exploration ); précédent : 001290; suivant : 001292Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.
Auteurs : Yong Zhao [République populaire de Chine] ; Chang-An Geng [République populaire de Chine] ; Hao Chen [République populaire de Chine] ; Yun-Bao Ma [République populaire de Chine] ; Xiao-Yan Huang [République populaire de Chine] ; Tuan-Wu Cao [République populaire de Chine] ; Kang He [République populaire de Chine] ; Hao Wang [République populaire de Chine] ; Xue-Mei Zhang [République populaire de Chine] ; Ji-Jun Chen [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2015.
Descripteurs français
- KwdFr :
- Acétophénones (), Acétophénones (isolement et purification), Acétophénones (pharmacologie), Antigènes de surface du virus de l'hépatite B (), Antiviraux (), Antiviraux (isolement et purification), Antiviraux (pharmacologie), Artemisia (), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Virus de l'hépatite B ().
- MESH :
- isolement et purification : Acétophénones, Antiviraux.
- pharmacologie : Acétophénones, Antiviraux.
- Acétophénones, Antigènes de surface du virus de l'hépatite B, Antiviraux, Artemisia, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Virus de l'hépatite B.
English descriptors
- KwdEn :
- Acetophenones (chemistry), Acetophenones (isolation & purification), Acetophenones (pharmacology), Antiviral Agents (chemistry), Antiviral Agents (isolation & purification), Antiviral Agents (pharmacology), Artemisia (chemistry), Dose-Response Relationship, Drug, Hepatitis B Surface Antigens (drug effects), Hepatitis B virus (drug effects), Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
- MESH :
- chemical , chemistry : Acetophenones, Antiviral Agents.
- chemical , drug effects : Hepatitis B Surface Antigens.
- chemical , isolation & purification : Acetophenones, Antiviral Agents.
- chemical , pharmacology : Acetophenones, Antiviral Agents.
- chemistry : Artemisia.
- drug effects : Hepatitis B virus.
- Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
Abstract
p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.
DOI: 10.1016/j.bmcl.2015.02.024
PubMed: 25737008
Affiliations:
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Le document en format XML
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<term>Antiviral Agents (isolation & purification)</term>
<term>Antiviral Agents (pharmacology)</term>
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<term>Dose-Response Relationship, Drug</term>
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<front><div type="abstract" xml:lang="en">p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.</div>
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<name sortKey="Cao, Tuan Wu" sort="Cao, Tuan Wu" uniqKey="Cao T" first="Tuan-Wu" last="Cao">Tuan-Wu Cao</name>
<name sortKey="Chen, Hao" sort="Chen, Hao" uniqKey="Chen H" first="Hao" last="Chen">Hao Chen</name>
<name sortKey="Chen, Ji Jun" sort="Chen, Ji Jun" uniqKey="Chen J" first="Ji-Jun" last="Chen">Ji-Jun Chen</name>
<name sortKey="Geng, Chang An" sort="Geng, Chang An" uniqKey="Geng C" first="Chang-An" last="Geng">Chang-An Geng</name>
<name sortKey="He, Kang" sort="He, Kang" uniqKey="He K" first="Kang" last="He">Kang He</name>
<name sortKey="Huang, Xiao Yan" sort="Huang, Xiao Yan" uniqKey="Huang X" first="Xiao-Yan" last="Huang">Xiao-Yan Huang</name>
<name sortKey="Ma, Yun Bao" sort="Ma, Yun Bao" uniqKey="Ma Y" first="Yun-Bao" last="Ma">Yun-Bao Ma</name>
<name sortKey="Wang, Hao" sort="Wang, Hao" uniqKey="Wang H" first="Hao" last="Wang">Hao Wang</name>
<name sortKey="Zhang, Xue Mei" sort="Zhang, Xue Mei" uniqKey="Zhang X" first="Xue-Mei" last="Zhang">Xue-Mei Zhang</name>
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