Antipoliovirus structure-activity relationships of some aporphine alkaloids.
J Nat Prod
; 61(4): 480-4, 1998 Apr.
Article
in En
| MEDLINE
| ID: mdl-9584402
ABSTRACT
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).
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Antiviral Agents
/
Aporphines
/
Poliovirus
/
Alkaloids
Limits:
Animals
/
Humans
Language:
En
Journal:
J Nat Prod
Year:
1998
Document type:
Article
Affiliation country: