7,8,3'-Trihydroxyflavone

7,8,3'-Trihydroxyflavone
Clinical data
Other names	7,8,3'-THF
ATC code	None;
Identifiers
	IUPAC name 7,8-Dihydroxy-2-(3-hydroxyphenyl)chromen-4-one;
CAS Number	137502-84-2;
PubChem CID	676310;
ChemSpider	589045;
UNII	F67B8S3MH9;
ChEMBL	ChEMBL225513;
CompTox Dashboard (EPA)	DTXSID00350274 ;
Chemical and physical data
Formula	C15H10O5
Molar mass	270.240 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC(=CC(=C1)O)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O;
	InChI InChI=1S/C15H10O5/c16-9-3-1-2-8(6-9)13-7-12(18)10-4-5-11(17)14(19)15(10)20-13/h1-7,16-17,19H; Key:ZJZSQGDOCUHCCW-UHFFFAOYSA-N;

7,8,3′-Trihydroxyflavone (7,8,3'-THF) is a flavone and small-molecule agonist of TrkB, the main receptor of brain-derived neurotrophic factor (BDNF), that was derived from tropoflavin (7,8-DHF).^[1]^[2] Relative to tropoflavin, 7,8,3'-THF is 2–3-fold more potent in vitro as a TrkB agonist.^[1]^[2] 7,3'-Dihydroxyflavone (7,3'-DHF) is also more potent than tropoflavin in vitro, indicating that a 3'-hydroxy group on the B-ring enhances TrkB agonistic activity.^[1] 7,8,3'-THF has been tested in vivo and was found to produce TrkB-dependent neuroprotective effects in mice similarly to tropoflavin.^[2]^[3]

References

^ ^a ^b ^c Liu X, Chan CB, Jang SW, Pradoldej S, Huang J, He K, et al. (December 2010). "A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect". Journal of Medicinal Chemistry. 53 (23): 8274–86. doi:10.1021/jm101206p. PMC 3150605. PMID 21073191.
^ ^a ^b ^c Yu Q, Chang Q, Liu X, Gong S, Ye K, Lin X (June 2012). "7,8,3'-Trihydroxyflavone, a potent small molecule TrkB receptor agonist, protects spiral ganglion neurons from degeneration both in vitro and in vivo". Biochemical and Biophysical Research Communications. 422 (3): 387–92. doi:10.1016/j.bbrc.2012.04.154. PMC 3388121. PMID 22575512.
^ Yu Q, Chang Q, Liu X, Wang Y, Li H, Gong S, et al. (August 2013). "Protection of spiral ganglion neurons from degeneration using small-molecule TrkB receptor agonists". The Journal of Neuroscience. 33 (32): 13042–52. doi:10.1523/JNEUROSCI.0854-13.2013. PMC 3735884. PMID 23926258.

[LiuChan2010-1] Liu X, Chan CB, Jang SW, Pradoldej S, Huang J, He K, et al. (December 2010). "A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect". Journal of Medicinal Chemistry. 53 (23): 8274–86. doi:10.1021/jm101206p. PMC 3150605. PMID 21073191.

[YuChang2012-2] Yu Q, Chang Q, Liu X, Gong S, Ye K, Lin X (June 2012). "7,8,3'-Trihydroxyflavone, a potent small molecule TrkB receptor agonist, protects spiral ganglion neurons from degeneration both in vitro and in vivo". Biochemical and Biophysical Research Communications. 422 (3): 387–92. doi:10.1016/j.bbrc.2012.04.154. PMC 3388121. PMID 22575512.

[YuChang2013-3] Yu Q, Chang Q, Liu X, Wang Y, Li H, Gong S, et al. (August 2013). "Protection of spiral ganglion neurons from degeneration using small-molecule TrkB receptor agonists". The Journal of Neuroscience. 33 (32): 13042–52. doi:10.1523/JNEUROSCI.0854-13.2013. PMC 3735884. PMID 23926258.

[1]

[2]

[3]

See also

References