4'-Dimethylamino-7,8-dihydroxyflavone

4'-Dimethylamino-7,8-dihydroxyflavone

Systematic (IUPAC) name
2-[4-(Dimethylamino)phenyl]-7,8-dihydroxy-4H-chromen-4-one
Identifiers
CAS Number	1205548-04-4
ATC code	None
ChemSpider	26630138
Chemical data
Formula	C17H15NO4
Molar mass	297.3053 g/mol
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

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

See also

• 7,8,3'-Trihydroxyflavone
• R7
• Deoxygedunin
• HIOC
• N-Acetylserotonin

References

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.
2. Liu, Xia; Chan, Chi-Bun; Qi, Qi; Xiao, Ge; Luo, Hongbo R.; He, Xiaolin; Ye, Keqiang (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): 8524–8537. doi:10.1021/jm301099x. ISSN 0022-2623.
3. Liu, Chaoyang; Chan, Chi Bun; Ye, Keqiang (2016). "7,8-dihydroxyflavone, a small molecular TrkB agonist, is useful for treating various BDNF-implicated human disorders". Translational Neurodegeneration 5 (1). doi:10.1186/s40035-015-0048-7. ISSN 2047-9158.
4. Zeng, Yan; Wang, Xiaonan; Wang, Qiang; Liu, Shumin; Hu, Xiamin; McClintock, Shawn (2013). "Small Molecules Activating TrkB Receptor for Treating a Variety of CNS Disorders". CNS & Neurological Disorders - Drug Targets 12 (7): 1066–1077. doi:10.2174/18715273113129990089. ISSN 1871-5273.
5. Jiang, M.; Peng, Q.; Liu, X.; Jin, J.; Hou, Z.; Zhang, J.; Mori, S.; Ross, C. A.; Ye, K.; Duan, W. (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): 2462–2470. doi:10.1093/hmg/ddt098. ISSN 0964-6906.