Ascofuranone
| Ascofuranone
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| 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
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| Other names
| Ascofuranon
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| Identifiers
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| CAS number
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| 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
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| Properties
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| Molar mass
| 420.926 g mol-1
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Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
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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.
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