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


PABUCCUOGLU V. , ROZWADOWSKA M. D. , BROSSİ A., CLARK A., HUFFORD C. D. , GEORGE C., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.324, ss.29-33, 1991 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 324 Konu: 1
  • Basım Tarihi: 1991
  • Doi Numarası: 10.1002/ardp.19913240109
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Sayfa Sayıları: ss.29-33

Özet

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).