FL3 (flavagline)

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
CAS Number	1186012-80-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL556074;
ChemSpider	24623199;
PubChem CID	44233671;
UNII	FTL3D4LRE3 ;
CompTox Dashboard (EPA)	DTXSID801030080 ;
	InChI 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;
	SMILES 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
Chemical formula	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

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]

References

^ 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.
^ 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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[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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