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Ascofuranone

Ascofuranone

IUPAC name	3-Chloro-5-[(2E,6E)-7-(5,5-dimethyl-4- oxotetrahydro-2-furanyl)-3-methyl-2,6- octadien-1-yl]-4,6-dihydroxy-2-methylbenzaldehyde
Other names	Ascofuranon
Identifiers
CAS number
SMILES	Oc2c(C=O)c(C)c(Cl)c(O)c2C\C=C(/C) CC\C=C(/C)[C@@H]1CC(=O)C(C)(C)O1
Properties
Molar mass	420.926 g mol^-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ascofuranone is an antibiotic produced by the fungus Ascochyta visiae^[1] that inhibits the Trypanosoma brucei alternative oxidase and is a lead compound in efforts to produce other drugs targeting this enzyme for the treatment of sleeping sickness.^[2] The compound is effective both in vitro cell culture and in infections in mice.^[1]

Ascofuranone has also been reported to have anti-tumor activity,^[3] and modulate the immune system.^[4]

References

^ ^a ^b Yabu Y, Yoshida A, Suzuki T, Nihei C, Kawai K, Minagawa N, Hosokawa T, Nagai K, Kita K, Ohta N (2003). "The efficacy of ascofuranone in a consecutive treatment on Trypanosoma brucei brucei in mice". Parasitol. Int. 52 (2): 155-64. PMID 12798927.
^ Minagawa N, Yabu Y, Kita K, Nagai K, Ohta N, Meguro K, Sakajo S, Yoshimoto A (1997). "An antibiotic, ascofuranone, specifically inhibits respiration and in vitro growth of long slender bloodstream forms of Trypanosoma brucei brucei". Mol. Biochem. Parasitol. 84 (2): 271-80. PMID 9084049.
^ Magae J, Hayasaki J, Matsuda Y, Hotta M, Hosokawa T, Suzuki S, Nagai K, Ando K, Tamura G (1988). "Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes". J. Antibiot. 41 (7): 959-65. PMID 3417568.
^ Magae J, Suzuki S, Nagai K, Yamasaki M, Ando K, Tamura G (1986). "In vitro effects of an antitumor antibiotic, ascofuranone, on the murine immune system". Cancer Res. 46 (3): 1073-8. PMID 3080231.