α-Naphthoflavone

α-Naphthoflavone, also known as 7,8-benzoflavone and 2-phenyl-benzo[h]chromen-4-one, is a synthetic[1][2] flavone derivative. It can be prepared from 2-naphthol and cinnamaldehyde.[3]

α-Naphthoflavone
Names
IUPAC name
Benzo[7,8]flavone
Systematic IUPAC name
2-Phenyl-4H-naphtho[1,2-b]pyran-4-one
Other names
7,8-Benzoflavone
ANF
2-Phenyl-benzo[h]chromen-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.009.156
EC Number
  • 210-071-1
UNII
  • InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H checkY
    Key: VFMMPHCGEFXGIP-UHFFFAOYSA-N checkY
  • InChI=1/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
    Key: VFMMPHCGEFXGIP-UHFFFAOYAW
  • O=C\1c4c(O/C(=C/1)c2ccccc2)c3ccccc3cc4
Properties
C19H12O2
Molar mass 272.303 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

α-Naphthoflavone is a potent inhibitor of the enzyme aromatase, the enzyme that converts testosterone to estrogen.[1][2] α-Naphthoflavone has been shown to cause abnormal testicular development in young chickens.[4]

See also

References
  1. Campbell, Deborah R.; Kurzer, Mindy S. (1993). "Flavonoid inhibition of aromatase enzyme activity in human preadipocytes". Journal of Steroid Biochemistry and Molecular Biology. 46 (3): 381–388. doi:10.1016/0960-0760(93)90228-O. PMID 9831487. S2CID 25861427.
  2. Kellis JT Jr; Vickery LE (1984). "Inhibition of human estrogen synthetase (aromatase) by flavones". Science. 225 (4666): 1032–1034. Bibcode:1984Sci...225.1032K. doi:10.1126/science.6474163. PMID 6474163.
  3. Harvey, Ronald G.; Hahn, Jung Tai; Bukowska, Maria; Jackson, Henry (1990). "A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones". The Journal of Organic Chemistry. 55 (25): 6161. doi:10.1021/jo00312a023.
  4. Trefil, P.; Micakova, A.; Stiborova, M.; Poplstein, M.; Brillard, J.P.; Hodek, P. (2004). "Effects of alpha-naphthoflavone on body growth and gonad development in chickens (Gallus domesticus)". Czech Journal of Animal Science. 49 (6): 231–238. doi:10.17221/4305-CJAS.


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