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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL121987 ;
ChemSpider	324633 ;
PubChem CID	365701;
CompTox Dashboard (EPA)	DTXSID30327131 ;
	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

Anchel, M.; Hervey, A.; Robbins, W. J. Proc. Natl. Acad. Sci. U.S.A. 1950, 36, 300
http://clinicaltrials.gov/ct2/results?term=HMAF&Search=Search
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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[1] Anchel, M.; Hervey, A.; Robbins, W. J. Proc. Natl. Acad. Sci. U.S.A. 1950, 36, 300

[2] ttp://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.)