Acylfulvene

Acylfulvene

Names
IUPAC name (5'R)-5'-hydroxy-2',5',7'-trimethyl-4'-spiro[cyclopropane-1,6'-indene]one
Identifiers
CAS Number	125392-76-9
ChEMBL	ChEMBL121987
ChemSpider	324633
Jmol 3D model	Interactive image Interactive image
PubChem	365701
InChI 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 Key: HLAKJNQXUARACO-ZDUSSCGKSA-N 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
SMILES 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
Chemical formula	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. http://clinicaltrials.gov/ct2/results?term=HMAF&Search=Search
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.)