A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore.
The synthesis of 3-deoxydihydrolycoricidine, a key element toward elucidation of the pancratistatin anticancer pharmacophore, is described. Biological evaluation of this compound showed it to be significantly less active against tumor cells than pancratistatin. In addition to those features previously identified, the requirement of a 2,3,4-triol functionalized ring-C is now definitely established as the minimum pharmacophoric element for potent anticancer activity.
McNulty
James
J
Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ont., Canada L8S 4M1. jmcnult@mcmaster.ca
Larichev
Vladimir
V
Pandey
Siyaram
S
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D018360:Crystallography, X-Ray; D006801:Humans; D007546:Isoquinolines / Q000737:chemistry* / Q000627:therapeutic use; D009369:Neoplasms / Q000188:drug therapy; D010617:Phenanthridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D014407:Tumor Cells, Cultured
C507192:3-deoxydihydrolycoricidine; D047151:Amaryllidaceae Alkaloids; D000970:Antineoplastic Agents; D007546:Isoquinolines; D010617:Phenanthridines; C044997:pancratistatin