Betulonic amides modified at the ring A by amino acids: synthesis and inhibition of influenza A virus reproduction

The Beckman rearrangement of carboxy- and alkyloxycarbonylalkylamides of 3-hydroxyiminobetulonic acid led to derivatives of 3a-homo-4-aza-3-oxolup-20(29)-ene and 3,4-seco-2-cyanolupa-4(23),20(29)-diene. An X-ray analysis showed methyl 3-(N-acetoximino)lup-20(29)-enoate is the E-isomer. The compounds...

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Bibliographic Details
Published in:	Bioorganicheskaia khimiia Vol. 35; no. 1; p. 129
Main Authors:	Flekhter, O B, Medvedeva, N I, Tolstikov, G A, Savinova, O V, Boreko, E I, Dolgushin, F M
Format:	Journal Article
Language:	Russian
Published:	Russia (Federation) 01-01-2009
Subjects:	Amides - chemical synthesis Amides - chemistry Amides - pharmacology Amino Acids - chemistry Animals Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Cells, Cultured Chick Embryo Crystallography, X-Ray Fibroblasts - virology Influenza A virus - drug effects Influenza A virus - physiology Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemical synthesis Oleanolic Acid - chemistry Oleanolic Acid - pharmacology Virus Replication - drug effects
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Summary:	The Beckman rearrangement of carboxy- and alkyloxycarbonylalkylamides of 3-hydroxyiminobetulonic acid led to derivatives of 3a-homo-4-aza-3-oxolup-20(29)-ene and 3,4-seco-2-cyanolupa-4(23),20(29)-diene. An X-ray analysis showed methyl 3-(N-acetoximino)lup-20(29)-enoate is the E-isomer. The compounds synthesized exhibited inhibiting activity toward the reproduction of flu A virus in cell culture.
ISSN:	0132-3423