Monomeric and dimeric arylisoquinoline alkaloids and derivatives thereof

US6140339A · kind A · utility

Assignee

• The United States of America, as represented by the Department of Health and Human Services · US

Inventors

• Gerhard Bringmann · Würzburg, DE
• Michael R. Boyd · Mobile, US
• Matthias S. Wenzel · Jena, DE

Key dates

• Filing date: Dec 31, 1997
• Grant date: Oct 31, 2000
• Expiry date: Dec 31, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D217/24
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention provides new monomeric derivatives of the C-8'-7 linked naphthylisoquinoline alkaloid dioncophylline D. The invention also provides new C-4 substituted monomeric arylisoquinoline alkaloid derivatives. The present invention furthermore provides novel dimeric arylisoquinoline alkaloids comprised of coupled first and second arylisoquinoline monomers, wherein either or both of said monomer(s) is (are) monomeric compound(s) of the present invention. Monomeric and dimeric compounds of the present invention have medically useful properties, such as antimicrobial properties, more specifically such as antimalarial and antiviral properties. Monomeric compounds of the present invention are also useful as building blocks or intermediates for synthesis of novel dimeric arylisoquinoline alkaloids. Monomeric and dimeric compounds of the present invention may be obtained in substantially pure form by total synthesis, partial synthesis, or derivatization from known synthetic or naturally occurring compounds, and by isolation and purification from plants of the Dioncophyllaceae and Ancistrocladaceae families.