Oxoaporphine Alkaloids: Conversion of Lysicamine into Liriodendronine and its 2‐O‐Methyl Ether, and Antifungal Activity
作者:
Varol Pabuccuoglu,
Maria Danka Rozwadowska,
Arnold Brossi,
Alice Clark,
Charles D. Hufford,
Clifford George,
Judith L. Flippen‐Anderson,
期刊:
Archiv der Pharmazie
(WILEY Available online 1991)
卷期:
Volume 324,
issue 1
页码: 29-33
ISSN:0365-6233
年代: 1991
DOI:10.1002/ardp.19913240109
出版商: WILEY‐VCH Verlag
数据来源: WILEY
摘要:
AbstractPschorrreaction of diazonium salt7in aqueous methanolic sulfuric acid afforded, besides lysicamine2, the orange colored sulfate of oxodibenzopyrrocoline (8). The structure is fully supported by an X‐ray analysis of its picrate salt. Selective ether cleavage of lysicamine (2) with 48% HBr afforded a hydrobromide of9, and free betaine9on treatment with pyridine‐water. Both compounds methylated on treatment with etherial diazomethane on nitrogen to give the known 2‐O N‐dimethylliriodendronine (11). Liriodendronine (10) was obtained from lysicamine (2) on heating with pyridine ·HBr at 189°C, and treatment with pyridine‐water, as a dark violet betaine. Betaine12was obtained by heating11·HCl to 200°C. The quaternary salts of lysicamine, lysicamine methiodide (3) and lysicamine methosulfate (4) were comparable in anticandidal activity to liriodenine (1), but were not as active as liriodenine me
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