(Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties

  • J Nat Prod. 1996 Sep;59(9):896-9. doi: 10.1021/np960450y.
T C McMorris  1 ,  M J Kelner ,  W Wang ,  J Yu ,  L A Estes ,  R Taetle
Affiliations
  • 1. Department of Chemistry, University of California at San Diego, La Jolla, 92093-0506, USA.
PMID: 8864242 DOI: 10.1021/np960450y
Abstract

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.