Arabilin

Arabilin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C28H31NO6/c1-17(11-18(2)13-22-7-9-24(10-8-22)29(31)32)12-19(3)14-23-15-25(34-16-23)27-20(4)26(30)21(5)28(33-6)35-27/h7-10,12-14,16,25H,11,15H2,1-6H3/b17-12-,18-13+,19-14- Y
    Key: VDYKJNNKAHKFAL-GQEYKGHLSA-N Y
  • CC1=C(OC(=C(C1=O)C)OC)C2CC(=CO2)/C=C(/C)\C=C(\C)/C/C(=C/C3=CC=C(C=C3)[N+](=O)[O-])/C
Properties
C28H31NO6
Molar mass 477.557 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Arabilin is a chemical compound with the molecular formula C28H31NO6. It was first isolated from the MK756-CF1 strain of Streptomyces in 2010.[1] Chemically, it contains a substituted γ-pyrone ring and a p-nitrophenyl group that is rarely found in nature.

Arabilin acts as an androgen antagonist,[1] and therefore has attracted research interest in its potential pharmacological use.[2][3] A laboratory synthesis of arabilin has been reported.[4][5]

Related compounds also isolated from Streptomyces include spectinabilin and SNF4435C.[1]

References

  1. ^ a b c Kawamura, Tatsuro; Fujimaki, Takahiro; Hamanaka, Natsuki; Torii, Kentaro; Kobayashi, Hiroki; Takahashi, Yoshikazu; Igarashi, Masayuki; Kinoshita, Naoko; Nishimura, Yoshio; Tashiro, Etsu; Imoto, Masaya (2010). "Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1". The Journal of Antibiotics. 63 (10): 601–605. doi:10.1038/ja.2010.98. PMID 20736953.
  2. ^ Fujimaki, Takahiro; Saito, Shun; Imoto, Masaya (2017). "Arabilin overcomes resistance to AR-targeted therapy". The Journal of Antibiotics. 70 (3): 328–330. doi:10.1038/ja.2016.162. PMID 28074047.
  3. ^ Imoto, Masaya; Fujimaki, Takahiro; Saito, Shun; Tashiro, Etsu (2021). "Androgen receptor antagonists produced by Streptomyces overcome resistance to enzalutamide". The Journal of Antibiotics. 74 (10): 706–716. doi:10.1038/s41429-021-00453-y. PMID 34282313.
  4. ^ Lim, Hee Nam; Parker, Kathlyn A. (2011). "Total Synthesis of the Potent Androgen Receptor Antagonist (−)-Arabilin: A Strategic, Biomimetic [1,7]-Hydrogen Shift". Journal of the American Chemical Society. 133 (50): 20149–20151. Bibcode:2011JAChS.13320149L. doi:10.1021/ja209459f. PMC 3320024. PMID 22085260.
  5. ^ "Synthesis of (–)-Arabilin". Synfacts. 8 (3): 0242. 2012. doi:10.1055/s-0031-1290244.
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