FL3 (flavagline)

FL3 is a synthetic flavagline that displays potent anticancer and cardioprotectant activities. This compound induces the death of cancer cells by an original mechanism that involves the apoptosis-inducing factor and caspase 12, suggesting that it may improve the efficacy of cancer chemotherapies. It was also shown that FL3 may enhance the efficacy of one of the most widely used anticancer agents, doxorubicin, and alleviate its main adverse effect, cardiac damage.[1][2]

FL3
Names
Preferred IUPAC name
(1R,3S,3aR,8bS)-3a-(4-Bromophenyl)-6,8-dimethoxy-3-phenyl-1,2,3,3a-tetrahydro-8bH-cyclopenta[b][1]benzofuran-1,8b-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C25H23BrO5/c1-29-18-12-20(30-2)23-21(13-18)31-25(16-8-10-17(26)11-9-16)19(14-22(27)24(23,25)28)15-6-4-3-5-7-15/h3-13,19,22,27-28H,14H2,1-2H3/t19-,22+,24+,25-/m0/s1
    Key: ACIXIVSDWSWVDW-MCWSDJLFSA-N
  • InChI=1/C25H23BrO5/c1-29-18-12-20(30-2)23-21(13-18)31-25(16-8-10-17(26)11-9-16)19(14-22(27)24(23,25)28)15-6-4-3-5-7-15/h3-13,19,22,27-28H,14H2,1-2H3/t19-,22+,24+,25-/m0/s1
    Key: ACIXIVSDWSWVDW-MCWSDJLFBB
  • O[C@@]12[C@@]([C@H](C3=CC=CC=C3)C[C@H]2O)(C4=CC=C(Br)C=C4)OC5=CC(OC)=CC(OC)=C51
Properties
C25H23BrO5
Molar mass 483.358 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

References
  1. Thuaud, F.; Bernard, Y.; Türkeri, G.; Dirr, R; Aubert, G.; Cresteil, T.; Baguet, A.; Tomasetto, C.; Svitkin, Y; Sonenberg, N.; Nebigil, C.; Désaubry, L. (2009). "Synthetic Analogue of Rocaglaol Displays a Potent and Selective Cytotoxicity in Cancer Cells: Involvement of Apoptosis Inducing Factor and Caspase-12". Journal of Medicinal Chemistry. 52 (16): 5176–5187. doi:10.1021/jm900365v. PMID 19655762.
  2. Bernard, Y.; Ribeiro, N.; Thuaud, F.; Türkeri, G.; Dirr, R.; Boulberdaa, M.; Nebigil, C.; Désaubry, L. (2011). "Flavaglines Alleviate Doxorubicin Cardiotoxicity: Implication of Hsp27". PLoS ONE. 6 (10): e25302. Bibcode:2011PLoSO...625302B. doi:10.1371/journal.pone.0025302. PMC 3204970. PMID 22065986.


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