Acylfulvene
Names
Preferred IUPAC name
(6′R)-6′-Hydroxy-2′,4′,6′-trimethylspiro[cyclopropane-1,5′-inden]-7′(6′H)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C14H16O2/c1-8-6-10-9(2)14(4-5-14)13(3,16)12(15)11(10)7-8/h6-7,16H,4-5H2,1-3H3/t13-/m0/s1 checkY
    Key: HLAKJNQXUARACO-ZDUSSCGKSA-N checkY
  • InChI=1/C14H16O2/c1-8-6-10-9(2)14(4-5-14)13(3,16)12(15)11(10)7-8/h6-7,16H,4-5H2,1-3H3/t13-/m0/s1
    Key: HLAKJNQXUARACO-ZDUSSCGKBE
  • CC1=CC2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C
  • O=C1C/3=C/C(=CC\3=C(/C2([C@]1(O)C)CC2)C)C
Properties
C14H16O2
Molar mass 216.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acylfulvene is a class of cytotoxic semi-synthetic derivatives of illudin, a natural product that can be extracted from the jack o'lantern mushroom (Omphalotus olearius).[1] One important acylfulvene, 6-hydroxymethylacylfulvene (irofulven), has been evaluated for the treatment of a wide assortment of cancers and tumors.[2] It is thought that acylfulvene compounds kill cancer cells by DNA alkylation (see DNA methylation).[3]

References

  1. ↑ Anchel, M.; Hervey, A.; Robbins, W. J. Proc. Natl. Acad. Sci. U.S.A. 1950, 36, 300
  2. ↑ "Search Details". Clinical Trials. Retrieved 22 March 2023.
  3. ↑ Woynarowski, Jan M.; Napier, Cheryl; Koester, Steven K.; Chen, Shih-Fong; Troyer, Dean; Chapman, William; Macdonald, John R. Biochemical Pharmacology (1997), 54 (11), 1181-1193 CODEN: BCPCA6; ISSN 0006-2952. (Elsevier Science Inc.)
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