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Irofulven

Names
IUPAC name (6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro-7'(6'H)-one
Identifiers
CAS Number	158440-71-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL118218
ChemSpider	130640
KEGG	D04614
PubChem CID	148189
CompTox Dashboard (EPA)	DTXSID50166423
InChI InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1Key: NICJCIQSJJKZAH-AWEZNQCLSA-N InChI=1/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1Key: NICJCIQSJJKZAH-AWEZNQCLBL
SMILES O=C1C/3=C/C(=C(C\3=C(/C2(1(O)C)CC2)C)CO)C
Properties
Chemical formula	C15H18O3
Molar mass	246.302 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is an antitumor agent. It belongs to the family of drugs called alkylating agents.

It inhibits the replication of DNA.

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in mushrooms of the genus Omphalotus. The compound was oringally synthesized by Dr. Trevor McMorris (UCSD) and found to have anticancer properties by Dr. Michael J Kelner (UCSD).

Synthesis

McMorris, Trevor C.; Staake, Michael D.; Kelner, Michael J. (2004). "Synthesis and Biological Activity of Enantiomers of Antitumor Irofulven". The Journal of Organic Chemistry. 69 (3): 619. doi:10.1021/jo035084j. PMID 14750783.

References

1. Escargueil AE, Poindessous V, Soares DG, Sarasin A, Cook PR, Larsen AK (2008). "Influence of irofulven, a transcription-coupled repair-specific antitumor agent, on RNA polymerase activity, stability and dynamics in living mammalian cells". J. Cell. Sci. 121 (Pt 8): 1275–83. doi:10.1242/jcs.023259. PMID 18388315. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
2. Kelner MJ, McMorris TC, Estes L, Wang W, Samson KM, Taetle R (1996). "Efficacy of HMAF (MGI-114) in the MV522 metastatic lung carcinoma xenograft model nonresponsive to traditional anticancer agents". Invest New Drugs. 14 (2): 161–7. doi:10.1007/BF00210787. PMID 8913837.{{cite journal}}: CS1 maint: multiple names: authors list (link)
3. Wang Y, Wiltshire T, Senft J, Reed E, Wang W (2007). "Irofulven induces replication-dependent CHK2 activation related to p53 status". Biochem. Pharmacol. 73 (4): 469–80. doi:10.1016/j.bcp.2006.10.023. PMC 1800887. PMID 17118344. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
4. MacDonald JR, Muscoplat CC, Dexter DL, Mangold GL, Chen SF, Kelner MJ, McMorris TC, Von Hoff DD (1997). "Preclinical antitumor activity of 6-hydroxymethylacylfulvene, a semisynthetic derivative of the mushroom toxin illudin S". Cancer Res. 57 (2): 279–83. PMID 9000568.{{cite journal}}: CS1 maint: multiple names: authors list (link) Free full text

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