OXOAPORPHINE ALKALOIDS - CONVERSION OF LYSICAMINE INTO LIRIODENDRONINE AND ITS 2-O-METHYL ETHER, AND ANTIFUNGAL ACTIVITY

被引：12
作者：
PABUCCUOGLU, V
ROZWADOWSKA, MD
BROSSI, A
CLARK, A
HUFFORD, CD
GEORGE, C
FLIPPENANDERSON, JL
机构：
[1] UNIV MISSISSIPPI,SCH PHARM,DEPT PHARMACOGNOSY,UNIVERSITY,MS 38677
[2] USN,RES LAB,STRUCT MATTER LAB,WASHINGTON,DC 20375
来源：
ARCHIV DER PHARMAZIE | 1991年 / 324卷 / 01期
关键词：
D O I：
10.1002/ardp.19913240109
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Pschorr reaction of diazonium salt 7 in aqueous methanolic sulfuric acid afforded, besides lysicamine 2, 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 of 9, and free betaine 9 on 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-degrees-C, and treatment with pyridine-water, as a dark violet betaine. Betaine 12 was obtained by heating 11.HCl to 200-degrees-C. The quatemary 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 methiodide (13).
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页码：29 / 33
页数：5
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