Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors.
Identifieur interne : 001238 ( Main/Curation ); précédent : 001237; suivant : 001239Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors.
Auteurs : Gaopeng Song [République populaire de Chine] ; Xintian Shen [République populaire de Chine] ; Sumei Li [République populaire de Chine] ; Yibin Li [République populaire de Chine] ; Yunpeng Liu [États-Unis] ; Yushan Zheng [République populaire de Chine] ; Ruheng Lin [République populaire de Chine] ; Jihong Fan [République populaire de Chine] ; Hanming Ye [République populaire de Chine] ; Shuwen Liu [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2015.
Descripteurs français
- KwdFr :
- Animaux, Antiviraux (), Antiviraux (pharmacologie), Cellules HEK293, Cellules rénales canines Madin-Darby, Chiens, Humains, Pénétration virale (), Relation structure-activité, Sous-type H5N1 du virus de la grippe A (), Sous-type H5N1 du virus de la grippe A (physiologie), Triterpènes (), Triterpènes (pharmacologie), Tropanes ().
- MESH :
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Dogs, HEK293 Cells, Humans, Influenza A Virus, H5N1 Subtype (drug effects), Influenza A Virus, H5N1 Subtype (physiology), Madin Darby Canine Kidney Cells, Structure-Activity Relationship, Triterpenes (chemistry), Triterpenes (pharmacology), Tropanes (chemistry), Virus Internalization (drug effects).
- MESH :
- chemical , chemistry : Antiviral Agents, Triterpenes, Tropanes.
- chemical , pharmacology : Antiviral Agents, Triterpenes.
- drug effects : Influenza A Virus, H5N1 Subtype, Virus Internalization.
- physiology : Influenza A Virus, H5N1 Subtype.
- Animals, Dogs, HEK293 Cells, Humans, Madin Darby Canine Kidney Cells, Structure-Activity Relationship.
Abstract
A series of methyl ursolate 3-O-β-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3β-to 3α-forms was helpful to significantly improve the selective index while keeping their antiviral activities.
DOI: 10.1016/j.ejmech.2015.02.029
PubMed: 25728024
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pubmed:25728024Le document en format XML
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<front><div type="abstract" xml:lang="en">A series of methyl ursolate 3-O-β-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3β-to 3α-forms was helpful to significantly improve the selective index while keeping their antiviral activities. </div>
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