(Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties.
Reaction of the fungal sesquiterpene illudin S with excess paraformaldehyde in dilute H2SO4 gives (hydroxymethyl)acylfulvene. The primary allylic hydroxyl thus formed can undergo very facile replacement by a variety of nucleophiles. (Hydroxymethyl)acylfulvene (MGI.114) was more toxic than a precursor, acylfulvene, but less toxic than the parent compound illudin S to HL 60 cells.
McMorris
T C
TC
Department of Chemistry, University of California at San Diego, La Jolla, 92093-0506, USA.
Kelner
M J
MJ
Wang
W
W
Yu
J
J
Estes
L A
LA
Taetle
R
R
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001487:Basidiomycota / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008807:Mice, Inbred BALB C; D009368:Neoplasm Transplantation; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000302:isolation & purification* / Q000494:pharmacology
D000903:Antibiotics, Antineoplastic; D000970:Antineoplastic Agents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C102714:irofulven; C008105:illudin S