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;
ChEMBL	ChEMBL225513;
Chemical and physical data
Formula	C15H10O5
Molar mass	270.2369 g/mol 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 7,8-dihydroxyflavone (7,8-DHF).[1][2] Relative to 7,8-DHF, 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 7,8-DHF 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 7,8-DHF.[2][3]

References

Liu, Xia; Chan, Chi-Bun; Jang, Sung-Wuk; Pradoldej, Sompol; Huang, Junjian; He, Kunyan; Phun, Lien H.; France, Stefan; Xiao, Ge; Jia, Yonghui; Luo, Hongbo R.; Ye, Keqiang (2010). "A Synthetic 7,8-Dihydroxyflavone Derivative Promotes Neurogenesis and Exhibits Potent Antidepressant Effect". Journal of Medicinal Chemistry. 53 (23): 8274–8286. doi:10.1021/jm101206p. ISSN 0022-2623. PMC 3150605. PMID 21073191.
Yu, Qing; Chang, Qing; Liu, Xia; Gong, Shusheng; Ye, Keqiang; Lin, Xi (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): 387–392. doi:10.1016/j.bbrc.2012.04.154. ISSN 0006-291X. PMC 3388121. PMID 22575512.
Yu, Q.; Chang, Q.; Liu, X.; Wang, Y.; Li, H.; Gong, S.; Ye, K.; Lin, X. (2013). "Protection of Spiral Ganglion Neurons from Degeneration Using Small-Molecule TrkB Receptor Agonists". Journal of Neuroscience. 33 (32): 13042–13052. doi:10.1523/JNEUROSCI.0854-13.2013. ISSN 0270-6474. PMC 3735884. PMID 23926258.

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[LiuChan2010-1] Liu, Xia; Chan, Chi-Bun; Jang, Sung-Wuk; Pradoldej, Sompol; Huang, Junjian; He, Kunyan; Phun, Lien H.; France, Stefan; Xiao, Ge; Jia, Yonghui; Luo, Hongbo R.; Ye, Keqiang (2010). "A Synthetic 7,8-Dihydroxyflavone Derivative Promotes Neurogenesis and Exhibits Potent Antidepressant Effect". Journal of Medicinal Chemistry. 53 (23): 8274–8286. doi:10.1021/jm101206p. ISSN 0022-2623. PMC 3150605. PMID 21073191.

[YuChang2012-2] Yu, Qing; Chang, Qing; Liu, Xia; Gong, Shusheng; Ye, Keqiang; Lin, Xi (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): 387–392. doi:10.1016/j.bbrc.2012.04.154. ISSN 0006-291X. PMC 3388121. PMID 22575512.

[YuChang2013-3] Yu, Q.; Chang, Q.; Liu, X.; Wang, Y.; Li, H.; Gong, S.; Ye, K.; Lin, X. (2013). "Protection of Spiral Ganglion Neurons from Degeneration Using Small-Molecule TrkB Receptor Agonists". Journal of Neuroscience. 33 (32): 13042–13052. doi:10.1523/JNEUROSCI.0854-13.2013. ISSN 0270-6474. PMC 3735884. PMID 23926258.

7,8,3'-Trihydroxyflavone

See also

References