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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antibiotics, Antineoplastic / pharmacology
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Antineoplastic Agents / isolation & purification*
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Antineoplastic Agents / pharmacology
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Basidiomycota / chemistry*
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Chromatography, Thin Layer
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Crystallography, X-Ray
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Drug Screening Assays, Antitumor
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HL-60 Cells
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Humans
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Lung Neoplasms / drug therapy
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Magnetic Resonance Spectroscopy
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Mice
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Mice, Inbred BALB C
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Neoplasm Transplantation
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Polycyclic Sesquiterpenes
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
Substances
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Antibiotics, Antineoplastic
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Antineoplastic Agents
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Polycyclic Sesquiterpenes
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Sesquiterpenes
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irofulven
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illudin S