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{{chembox |
{{chembox |
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| Name = |
| Name = Ascofuranone |
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| ImageFile = Ascofuranone.png |
| ImageFile = Ascofuranone structure.png |
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| ImageSize = 200px |
| ImageSize = 200px |
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| ImageName = Chemical structure of |
| ImageName = Chemical structure of ascofuranone |
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| IUPACName = |
| IUPACName = 5-chloro-3-[(2''E'',6''E'')-7-[(2''S'')-5,5-dimethyl-4-oxo-tetrahydrofuran-2-yl]-3-methyl-octa-2,6-dienyl]-2,4-dihydroxy-6-methyl-benzaldehyde |
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| IUPACName_hidden = yes |
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oxotetrahydro-2-furanyl)-3-methyl-2,6- |
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octadien-1-yl]-4,6-dihydroxy-2-methylbenzaldehyde |
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| OtherNames = Ascofuranon |
| OtherNames = Ascofuranon |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| 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 |
| 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 |
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| ChemSpiderID = 4939184 |
| ChemSpiderID = 4939184 |
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| PubChem = 6434242 |
| PubChem = 6434242 |
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| 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 = 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 |
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| InChIKey = VGYPZLGWVQQOST-JUERRSSIBJ |
| InChIKey = VGYPZLGWVQQOST-JUERRSSIBJ |
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| CASNo =38462-04-3 |
| CASNo =38462-04-3 |
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}} |
}} |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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==References== |
==References== |
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{{reflist}} |
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<references/> |
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[[Category:Antibiotics]] |
[[Category:Antibiotics]] |
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[[Category:Lactones]] |
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[[Category:Polyphenols]] |
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[[Category:Terpenes and terpenoids]] |
[[Category:Terpenes and terpenoids]] |
Revision as of 18:46, 26 February 2010
Names | |
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IUPAC name
5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxo-tetrahydrofuran-2-yl]-3-methyl-octa-2,6-dienyl]-2,4-dihydroxy-6-methyl-benzaldehyde
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Other names
Ascofuranon
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C23H29ClO5 | |
Molar mass | 420.93 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. doi:10.1016/S1383-5769(03)00012-6. PMID 12798927.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link)