Antipoliovirus Structure−Activity Relationships of Some Aporphine Alkaloids

A series of 18 aporphinoids have been tested in vitro against human poliovirus. The aporphines (+)-glaucine fumarate (1), (+)-N-methyllaurotetanine (4), (+)-isoboldine (7), and (−)-nuciferine, HCl (10) were found to be active with selectivity indices >14. The nature of the 1,2-substituents of the...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1998-04, Vol.61 (4), p.480-484
Main Authors: Boustie, Joël, Stigliani, Jean-Luc, Montanha, Jarbas, Amoros, Maryvonne, Payard, Marc, Girre, Loïc
Format: Article
Language:English
Subjects:
ALCALOIDE QUINOLIQUE
ALCALOIDES DE LA QUINOLINA
Alkaloids - chemistry
Alkaloids - pharmacology
Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
ANTIMICROBIAL PROPERTIES
Antiviral agents
Antiviral Agents - chemistry
Antiviral Agents - pharmacology
ANTIVIRAL PROPERTIES
Aporphines - chemistry
Aporphines - pharmacology
Biological and medical sciences
Cercopithecus aethiops
CHEMICAL STRUCTURE
Cytopathogenic Effect, Viral - drug effects
ENTEROVIRUS
ESPECTROMETRIA
ESTRUCTURA QUIMICA
EXTRACTOS VEGETALES
EXTRAIT D'ORIGINE VEGETALE
Herpesvirus 1, Human - drug effects
HUMAN POLIOVIRUS
Humans
ISOQUINOLINE ALKALOIDS
Medical sciences
Models, Molecular
OXOAPORPHINES
Pharmacology. Drug treatments
PLANT EXTRACTS
Poliovirus - drug effects
PROPIEDADES ANTIMICROBIANAS
PROPRIETE ANTIMICROBIENNE
QUINOLINE ALKALOIDS
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
STRUCTURE CHIMIQUE
Structure-Activity Relationship
TETRAHYDROISOQUINOLINES
Vero Cells
Virus Replication - drug effects
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Summary:A series of 18 aporphinoids have been tested in vitro against human poliovirus. The aporphines (+)-glaucine fumarate (1), (+)-N-methyllaurotetanine (4), (+)-isoboldine (7), and (−)-nuciferine, HCl (10) were found to be active with selectivity indices >14. The nature of the 1,2-substituents of the isoquinoline moiety appeared to be critical for antipoliovirus activity. An SAR study demonstrated the importance of a methoxyl group at C-2 on the tetrahydroisoquinoline ring for the induction of antipoliovirus activity. Molecular modeling of some compounds in this series revealed the close similarities between the three-dimensional conformational features of the inactive 1,2-substituted derivatives (+)-boldine (6) and (+)-laurolitsine (5) with derivatives containing the 1,2-(methylenedioxy) moiety, which were generally found to be inactive as exemplified by (+)-cassythicine (9).
ISSN:0163-3864
1520-6025
DOI:10.1021/np970382v