Eutropoflavin

Eutropoflavin (4'-Dimethylamino-7,8-dihydroxyflavone) is a synthetic flavone and selective small-molecule agonist of TrkB, the main receptor of brain-derived neurotrophic factor (BDNF), which was derived from structural modification of tropoflavin (7,8-DHF).[1][2][3][4] Relative to tropoflavin, eutropoflavin possesses higher agonistic activity at TrkB, is significantly more potent than tropoflavin both in vitro and in vivo, and has a longer duration of action (peaking at 4 hours and "partially decaying" at 8~16 hours in rodents).[1][3] The compound has been found to produce neuroprotective and neurogenic effects in the brain and spinal chord as well as antidepressant-like effects in animals.[1][3][4][5]

Eutropoflavin
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 2-[4-(dimethylamino)phenyl]-7,8-dihydroxy-4H-chromen-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC17H15NO4
Molar mass297.310 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)c1ccc(cc1)c2cc(=O)c3ccc(c(c3o2)O)O
InChI
  • InChI=InChI=1S/C17H15NO4/c1-18(2)11-5-3-10(4-6-11)15-9-14(20)12-7-8-13(19)16(21)17(12)22-15/h3-9,19,21H,1-2H3
  • Key:YPAYCZOHGRSGJS-UHFFFAOYSA-N

See also
  • Tropomyosin receptor kinase B § Agonists

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. Liu X, Chan CB, Qi Q, Xiao G, Luo HR, He X, Ye K (October 2012). "Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression". Journal of Medicinal Chemistry. 55 (19): 8524–37. doi:10.1021/jm301099x. PMC 3491656. PMID 22984948.
  3. Liu C, Chan CB, Ye K (2016). "7,8-dihydroxyflavone, a small molecular TrkB agonist, is useful for treating various BDNF-implicated human disorders". Translational Neurodegeneration. 5 (1): 2. doi:10.1186/s40035-015-0048-7. PMC 4702337. PMID 26740873.
  4. Zeng Y, Wang X, Wang Q, Liu S, Hu X, McClintock SM (November 2013). "Small molecules activating TrkB receptor for treating a variety of CNS disorders". CNS & Neurological Disorders Drug Targets. 12 (7): 1066–77. doi:10.2174/18715273113129990089. PMID 23844685.
  5. Jiang M, Peng Q, Liu X, Jin J, Hou Z, Zhang J, et al. (June 2013). "Small-molecule TrkB receptor agonists improve motor function and extend survival in a mouse model of Huntington's disease". Human Molecular Genetics. 22 (12): 2462–70. doi:10.1093/hmg/ddt098. PMC 3658168. PMID 23446639.
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