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α-萘黄酮

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α-萘黄酮
IUPAC名
2-phenylbenzo[h]chromen-4-one
别名 7,8-Benzoflavone, ANF,2-phenylbenzo[h]chromen-4-one
识别
CAS号 604-59-1  checkY
PubChem 11790
ChemSpider 11297
SMILES
 
  • O=C\1c4c(O/C(=C/1)c2ccccc2)c3ccccc3cc4
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
InChIKey VFMMPHCGEFXGIP-UHFFFAOYAW
ChEBI 76995
DrugBank DB07453
性质
化学式 C19H12O2
摩尔质量 272.3 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

α-萘黄酮(又称7,8-苯并黄酮)是一种人工合成的[1][2]黄酮类衍生物,可以由2-萘酚肉桂醛制备而成。[3]

α-萘黄酮是一种强效的芳香化酶抑制剂[1][2]实验发现其能导致幼鸡的睾丸发育出现异常。[4]

参见

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参考资料

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  1. ^ 1.0 1.1 Campbell, Deborah R.; Kurzer, Mindy S. Flavonoid inhibition of aromatase enzyme activity in human preadipocytes. Journal of Steroid Biochemistry and Molecular Biology. 1993, 46 (3): 381–388. PMID 9831487. doi:10.1016/0960-0760(93)90228-O. 
  2. ^ 2.0 2.1 Kellis JT Jr; Vickery LE. Inhibition of human estrogen synthetase (aromatase) by flavones. Science. 1984, 225 (4666): 1032–1034. Bibcode:1984Sci...225.1032K. PMID 6474163. doi:10.1126/science.6474163. 
  3. ^ Harvey, Ronald G.; Hahn, Jung Tai; Bukowska, Maria; Jackson, Henry. A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones. The Journal of Organic Chemistry. 1990, 55 (25): 6161. doi:10.1021/jo00312a023. 
  4. ^ Trefil, P.; Micakova, A.; Stiborova, M.; Poplstein, M.; Brillard, J.P.; Hodek, P. Effects of alpha-naphthoflavone on body growth and gonad development in chickens (Gallus domesticus). Czech Journal of Animal Science - UZPI. 2004, 49 (6): 231–238. doi:10.17221/4305-CJAS.