Irofulven

^[1]

Irofulven

Names
IUPAC name (6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one
Identifiers
CAS Number	158440-71-2
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL118218
ChemSpider	130640
KEGG	D04614
PubChem	148189
UNII	6B799IH05A
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/s1 Key: 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/s1 Key: NICJCIQSJJKZAH-AWEZNQCLBL
SMILES O=C1C/3=C/C(=C(C\3=C(/C2([C@]1(O)C)CC2)C)CO)C
Properties
Chemical formula	C15H18O3
Molar mass	246.302 g/mol
Density	1.285 g/mL
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

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is an experimental antitumor agent.^[2][3] It belongs to the family of drugs called alkylating agents.

It inhibits the replication of DNA in cell culture.^[4]

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in the Jack 'o' Lantern mushroom (Omphalotus illudens). The compound was originally synthesized by Dr. Trevor McMorris and found to have anticancer properties in mice by Dr. Michael J Kelner.^[5]

Synthesis

McMorris, T. C.; Staake, M. D.; Kelner, M. J. (2004). "Synthesis and Biological Activity of Enantiomers of Antitumor Irofulven". The Journal of Organic Chemistry. 69 (3): 619–23. doi:10.1021/jo035084j. PMID 14750783.

References

1. Aktietorget
2. Escargueil, A. E.; Poindessous, V.; Soares, D. G.; Sarasin, A.; Cook, P. R.; Larsen, A. K. (April 2008). "Influence of Irofulven, a Transcription-Coupled Repair-Specific Antitumor Agent, on RNA Polymerase Activity, Stability and Dynamics in Living Mammalian Cells" (pdf). Journal of Cell Science. 121 (Pt 8): 1275–1283. doi:10.1242/jcs.023259. PMID 18388315.
3. Kelner, M. J.; McMorris, T. C.; Estes, L.; Wang, W.; Samson, K. M.; Taetle, R. (1996). "Efficacy of HMAF (MGI-114) in the MV522 Metastatic Lung Carcinoma Xenograft Model Nonresponsive to Traditional Anticancer Agents". Investigational New Drugs. 14 (2): 161–167. doi:10.1007/BF00210787. PMID 8913837.
4. Wang, Y.; Wiltshire, T.; Senft, J.; Reed, E.; Wang, W. (February 2007). "Irofulven Induces Replication-Dependent CHK2 Activation Related to p53 Status" (pdf). Biochemical Pharmacology. 73 (4): 469–480. doi:10.1016/j.bcp.2006.10.023. PMC 1800887. PMID 17118344.
5. MacDonald, J. R.; Muscoplat, C. C.; Dexter, D. L.; Mangold, G. L.; Chen, S. F.; Kelner, M. J.; McMorris, T. C.; Von Hoff, D. D. (1997). "Preclinical Antitumor Activity of 6-hydroxymethylacylfulvene, a Semisynthetic Derivative of the Mushroom Toxin Illudin S" (pdf). Cancer Research. 57 (2): 279–283. PMID 9000568.