| Revision as of 05:34, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 467360935 of page Alpha-Naphthoflavone for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 20:13, 22 October 2023 edit Headbomb (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, File movers, New page reviewers, Pending changes reviewers, Rollbackers, Template editors454,938 edits ce |
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{{lowercasetitle}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 456681449 |
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| verifiedrevid = 477319533 |
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|Name=''alpha''-Naphthoflavone |
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| Name=α-Naphthoflavone |
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|ImageFile=Naphthoflavone.png |
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| ImageFile=Naphthoflavone.png |
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|ImageSize=200px |
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| ImageSize=200px |
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|IUPACName=2-phenylbenzochromen-4-one |
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| IUPACName=Benzoflavone |
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| SystematicName=2-Phenyl-4''H''-naphthopyran-4-one |
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|OtherNames=7,8-Benzoflavone, ANF,2-phenylbenzochromen-4-one |
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| OtherNames=7,8-Benzoflavone<br>ANF<br>2-Phenyl-benzochromen-4-one |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| 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 |
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| 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 |
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| InChIKey = VFMMPHCGEFXGIP-UHFFFAOYAW |
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| InChIKey = VFMMPHCGEFXGIP-UHFFFAOYAW |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 76995 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 283196 |
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| ChEMBL = 283196 |
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| StdInChIKey = VFMMPHCGEFXGIP-UHFFFAOYSA-N |
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| StdInChIKey = VFMMPHCGEFXGIP-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 604-59-1 --> |
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| CASNo=604-59-1 |
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| PubChem= |
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| PubChem=11790 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB07453 |
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| DrugBank = DB07453 |
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| EC_number = 210-071-1 |
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| UNII = FML65D8PY5 |
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| DTXSID = DTXSID2040650 |
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| SMILES = O=C\1c4c(O/C(=C/1)c2ccccc2)c3ccccc3cc4 |
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| SMILES = O=C\1c4c(O/C(=C/1)c2ccccc2)c3ccccc3cc4 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=19 |H=12 |O=2 |
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| C=19 | H=12 | O=2 |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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'''α-Naphthoflavone''', also known as '''7,8-benzoflavone''' and '''2-phenyl-benzochromen-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> ] derivative. It can be prepared from ] and ].<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> |
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α-Naphthoflavone is a potent ] of the ] ], the enzyme that converts ] to ].<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> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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{{DEFAULTSORT:Naphthoflavone, Alpha-}} |
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] |
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] |
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] |
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{{Organic-compound-stub}} |