Ascofuranona

 
Ascofuranona
Nombre IUPAC
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
General
Fórmula estructural Imagen de la estructura
Fórmula molecular ?
Identificadores
Número CAS 38462-04-3[1]​
ChEBI 156148
ChEMBL 133046
ChemSpider 4939184
PubChem 6434242
UNII I31EFB9515
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=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
Propiedades físicas
Masa molar 420,93 g/mol
Valores en el SI y en condiciones estándar
(25 ℃ y 1 atm), salvo que se indique lo contrario.
[editar datos en Wikidata]

Ascofuranone es un antibiótico producido por el hongo Ascochyta viciae,[2]​ que inhibe la enzima Oxidasa Alternativa de Tripanosoma (TAO) y es un compuesto que sirve como cabeza de serie para la búsqueda de otros fármacos dirigidos a inhibir esta enzima para el tratamiento de la enfermedad del sueño.[3]​ El compuesto es eficaz tanto in vitro como en cultivo celular y en infecciones en ratones.[2]​

Ascofuranona también se ha informado que tiene actividad anti-tumoral,[4]​ y modula el sistema inmune.[5]​

Referencias

  1. ↑ Número CAS
  2. ↑ 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. doi:10.1016/S1383-5769(03)00012-6. 
  3. ↑ 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. doi:10.1016/S0166-6851(96)02797-1. 
  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. 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. 

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