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Arabilin

From Wikipedia, the free encyclopedia
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- checkY
    Key: VDYKJNNKAHKFAL-GQEYKGHLSA-N checkY
  • 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 mass477.557 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Arabilin is a chemical compound with the molecular formulaC28H31NO6. It was first isolated from the MK756-CF1 strain ofStreptomyces in 2010.[1] Chemically, it contains a substitutedγ-pyrone ring and ap-nitrophenyl group that is rarely found in nature.

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

Related compounds also isolated fromStreptomyces includespectinabilin andSNF4435C.[1]

References

[edit]
  1. ^abcKawamura, 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.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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