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7,8,3'-Trihydroxyflavone

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(Redirected from 7,8,3'-trihydroxyflavone) Chemical compound Pharmaceutical compound
7,8,3'-Trihydroxyflavone
Clinical data
Other names7,8,3'-THF
ATC code
  • None
Identifiers
IUPAC name
  • 7,8-Dihydroxy-2-(3-hydroxyphenyl)chromen-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H10O5
Molar mass270.240 g·mol
3D model (JSmol)
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). Relative to tropoflavin, 7,8,3'-THF is 2–3-fold more potent in vitro as a TrkB agonist. 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. 7,8,3'-THF has been tested in vivo and was found to produce TrkB-dependent neuroprotective effects in mice similarly to tropoflavin.

See also

References

  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.
  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.
  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.
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
  • Artocarpetin A
  • Artoindonesianin P
    • Sulfated glycosidesTheograndin I and II
    Polymers
    Drugs
    Growth factor receptor modulators
    Angiopoietin
    CNTF
    EGF (ErbB)
    EGF
    (ErbB1/HER1)
    ErbB2/HER2
    • Agonists: Unknown/none
    ErbB3/HER3
    ErbB4/HER4
    FGF
    FGFR1
    FGFR2
    FGFR3
    FGFR4
    Unsorted
    HGF (c-Met)
    IGF
    IGF-1
    IGF-2
    Others
    LNGF (p75)
    PDGF
    RET (GFL)
    GFRα1
    GFRα2
    GFRα3
    GFRα4
    Unsorted
    SCF (c-Kit)
    TGFβ
    Trk
    TrkA
    • Negative allosteric modulators: VM-902A
    TrkB
    TrkC
    VEGF
    Others
    • Additional growth factor receptor modulators: Cerebrolysin (neurotrophin mixture)
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