alpha-Naphthoflavone

*alpha*-Naphthoflavone
Names
	IUPAC name 2-phenylbenzo[h]chromen-4-one
	Other names 7,8-Benzoflavone, ANF,2-phenylbenzo[h]chromen-4-one
Identifiers
CAS Number	604-59-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:76995 ;
ChEMBL	ChEMBL283196 ;
ChemSpider	11297 ;
DrugBank	DB07453 ;
ECHA InfoCard	100.009.156
EC Number	210-071-1;
PubChem CID	11790;
UNII	FML65D8PY5;
CompTox Dashboard (EPA)	DTXSID2040650;
	InChI 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 Key: VFMMPHCGEFXGIP-UHFFFAOYSA-N ; 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;
	SMILES O=C\1c4c(O/C(=C/1)c2ccccc2)c3ccccc3cc4;
Properties
Chemical formula	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

alpha-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]

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

References

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.
Kellis JT Jr; Vickery LE (1984). "Inhibition of human estrogen synthetase (aromatase) by flavones". Science. 225 (4666): 1032–1034. doi:10.1126/science.6474163. PMID 6474163.
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.
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 - UZPI. 49 (6): 231–238.

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[Campbell-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.

[Kellis-2] Kellis JT Jr; Vickery LE (1984). "Inhibition of human estrogen synthetase (aromatase) by flavones". Science. 225 (4666): 1032–1034. 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 - UZPI. 49 (6): 231–238.

alpha-Naphthoflavone

See also

References