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	38462-04-3
PubChem	6434242
SMILES	O=Cc1c(O)c(c(O)c(Cl)c1C)C/C=C(/CC/C=C(\C)[C@H]2OC(C(=O)C2)(C)C)C
InChI	1/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
InChI key	VGYPZLGWVQQOST-JUERRSSIBJ
ChemSpider ID	4939184
Properties
Molecular formula	C23H29ClO5
Molar mass	420.93 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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]

[edit] References

1. ^ ^{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. doi:10.1016/S1383-5769(03)00012-6. PMID 12798927. 
2. ^ 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. doi:10.1016/S0166-6851(96)02797-1. PMID 9084049. 
3. ^ 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. 
4. ^ 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.