Ascofuranone

Ascofuranone

Names
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
Other names Ascofuranon
Identifiers
CAS Number	38462-04-3
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL133046
ChemSpider	4939184
PubChem	6434242
InChI InChI=1S/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 Key: VGYPZLGWVQQOST-JUERRSSISA-N 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 Key: VGYPZLGWVQQOST-JUERRSSIBJ
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
Properties
Chemical formula	C23H29ClO5
Molar mass	420.93 g·mol^−1
Density	1.207 g/mL
Boiling point	581.2 °C (1,078.2 °F; 854.4 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Ascofuranone is an antibiotic produced by various ascomycete fungi including Acremonium sclerotigenum^[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.^[3]

Ascofuranone has also been reported to have anti-tumor activity,^[4] and modulate the immune system.^[5]

References

1. Hijikawa Y, Matsuzaki M, Suzuki S, Inaoka DK, Tatsumi R, Kido Y, Kita K. "Re-identification of the ascofuranone-producing fungus Ascochyta viciae as Acremonium sclerotigenum". J. Antibiot. doi:10.1038/ja.2016.132. PMID 27804952.
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. 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.
4. 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. doi:10.7164/antibiotics.41.959. PMID 3417568.
5. 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.