Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Α-Naphthoflavone: Difference between pages

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| verifiedrevid = 477319533

| Name=α-Naphthoflavone

| ImageFile=Naphthoflavone.png

| ImageSize=200px

| IUPACName=Benzo[7,8]flavone

| SystematicName=2-Phenyl-4''H''-naphtho[1,2-''b'']pyran-4-one

| OtherNames=7,8-Benzoflavone<br>ANF<br>2-Phenyl-benzo[''h'']chromen-4-one

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 76995

| CASNo=604-59-1

| PubChem=11790

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| EC_number = 210-071-1

| UNII = FML65D8PY5

| DTXSID = DTXSID2040650

| C=19 | H=12 | O=2

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'''α-Naphthoflavone''', also known as '''7,8-benzoflavone''' and '''2-phenyl-benzo[''h'']chromen-4-one''', is a synthetic<ref name=Campbell>{{cite journal | title = Flavonoid inhibition of aromatase enzyme activity in human preadipocytes |author1=Campbell, Deborah R. |author2=Kurzer, Mindy S. | journal = Journal of Steroid Biochemistry and Molecular Biology | year = 1993 | volume = 46 | issue = 3 | pages = 381–388 | doi = 10.1016/0960-0760(93)90228-O | pmid = 9831487|s2cid=25861427 }}</ref><ref name=Kellis>{{cite journal |author1=Kellis JT Jr |author2=Vickery LE | title = Inhibition of human estrogen synthetase (aromatase) by flavones | journal = Science | year = 1984 | volume = 225 | issue = 4666 | pages = 1032–1034 | doi = 10.1126/science.6474163 | pmid = 6474163|bibcode=1984Sci...225.1032K }}</ref> [[flavone]] derivative. It can be prepared from [[2-naphthol]] and [[cinnamaldehyde]].<ref>{{cite journal | doi = 10.1021/jo00312a023 | title = A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones | year = 1990 | last1 = Harvey | first1 = Ronald G. | last2 = Hahn | first2 = Jung Tai | last3 = Bukowska | first3 = Maria | last4 = Jackson | first4 = Henry | journal = The Journal of Organic Chemistry | volume = 55 | issue = 25 | pages = 6161}}</ref>

α-Naphthoflavone is a potent [[enzyme inhibitor|inhibitor]] of the [[enzyme]] [[aromatase]], the enzyme that converts [[testosterone]] to [[estrogen]].<ref name=Campbell/><ref name=Kellis/> α-Naphthoflavone has been shown to cause abnormal testicular development in young chickens.<ref>{{cite journal |author1=Trefil, P. |author2=Micakova, A. |author3=Stiborova, M. |author4=Poplstein, M. |author5=Brillard, J.P. |author6=Hodek, P. | title = Effects of alpha-naphthoflavone on body growth and gonad development in chickens (Gallus domesticus) | journal = Czech Journal of Animal Science | year = 2004 | volume = 49 | issue = 6 | pages = 231–238|doi=10.17221/4305-CJAS |doi-access=free }}</ref>

==See also==

* [[beta-Naphthoflavone|β-Naphthoflavone]]

* [[C19H12O2|C₁₉H₁₂O₂]]

==References==

{{Reflist}}

{{DEFAULTSORT:Naphthoflavone, Alpha-}}

[[Category:CYP1A2 inhibitors]]

[[Category:Aromatase inhibitors]]

[[Category:Benzochromenes]]

[[Category:Flavonoids]]

{{Organic-compound-stub}}