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Naphthacenes

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Definition: Polyacenes with four ortho-fused benzene rings in a straight linear arrangement. This group is best known for the subclass called TETRACYCLINES.     
Examples Anthracyclines; Tetracyclines 		Other names Tetracenes; Benz(b)Anthracenes
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
doxorubicinolone  0   *Naphthacenes. J Pharmacol Exp Ther 2009 Apr;329(1):175-84
tetraceno(2,3-b)thiophene  0   *Naphthacenes *Thiophenes. J Am Chem Soc. 2008 Mar 19;130(11):3502-8
bisbenzotetracyclo(6.2.2.2(3,6).0(2,7))tetradeca-4,9,11,13-tetraene  0   *Bridged Compounds *Naphthacenes. J Mol Model 2007 Dec;13(12):1215-20
pentacene  0   *Naphthacenes. J Phys Chem B 2007 Aug 16;111(32):9513-8
4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene carboxamide  0   *Naphthacenes. Bioorg Med Chem Lett. 2007 Feb 1;17(3):645-8
naphthacene  0   *Naphthacenes.
4-demethoxy-1,4-dimethyldaunomycinone  0   *Naphthacenes. Bioorg Med Chem 2002 Mar;10(3):621-4
6,13-pentacenequinone  0   *Naphthacenes *Quinones. Spectrochim Acta A Mol Biomol Spectrosc 2002 Apr;58(6):1201-8
5,12-naphthacenequinone  0   *Naphthacenes *Quinones. Spectrochim Acta A Mol Biomol Spectrosc 2002 Apr;58(6):1201-8
hibarimicinone  0   *Glycosides *Naphthacenes src-Family Kinases/antagonists & inhibitors. J Antibiot (Tokyo) 2002 Mar;55(3):270-8
hibarimicin B  0   *Glycosides *Naphthacenes src-Family Kinases/antagonists & inhibitors. J Antibiot (Tokyo) 2002 Mar;55(3):270-8
4,8-di-O-methyl-saintopin1,10,11-trihydroxy-3,8-dimethoxy-naphthacene-5,12-dione  0   *Naphthacenes. Bioorg Med Chem 2002 Feb;10(2):253-60
1,3,8,11-tetrahydroxy-naphthacene-5,12-dione(10-deoxysaintopin)  0   *Naphthacenes. Bioorg Med Chem 2002 Feb;10(2):253-60
2-methoxyrhamnosyltetracenomycin C  0   Glycosides Naphthacenes. J Biol Chem 2001 Jun 1;276(22):18765-74
rhamnosyltetracenomycin C  0   Glycosides Naphthacenes. J Biol Chem 2001 Jun 1;276(22):18765-74
2,4,8,11-tetrahydroxy-15-methyl-11,12,14,15-tetrahydro-17-oxahexaphene-1,3,10-trione  0   *Naphthacenes.
TMC 66  0   *Naphthacenes. J Antibiot (Tokyo) 1999 Jul;52(7):607-12
quanolirone II  0   *Glycosides *Naphthacenes. J Nat Prod 1998 Nov;61(11):1379-82
quanolirone I  0   *Glycosides *Naphthacenes. J Nat Prod 1998 Nov;61(11):1379-82
5,6-dihydrobenzo(a)naphthacenequinone  0   *Naphthacenes *Quinones. J Antibiot (Tokyo) 1997 Aug;50(8):685-9
XR651  0   Naphthacenes. J Antibiot (Tokyo) 1997 Feb;50(2):169-71
BMS 192548  0   *Naphthacenes Receptors, Neuropeptide Y/antagonists & inhibitors. J Antibiot (Tokyo) 1995 Oct;48(10):1060-5
6-hydroxytetracenomycin C  0   Naphthacenes. J Bacteriol 1995 Nov;177(21):6126-36
tetrabenzo(de,hi,mn,qr)naphthacene  0   *Naphthacenes. Carcinogenesis 1994 Dec;15(12):2931-6
UCE 1022  0   *Naphthacenes. J Antibiot (Tokyo) 1994 Aug;47(8):949-51
tetracenomycin F1  149791-45-7 2-Naphthacenecarboxylic acid, 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-11-oxo  *Naphthacenes. J Nat Prod 1993 Aug;56(8):1288-93
bequinostatin D  152175-75-2 Benzo(a)naphthacene-8,13-dione, 1,7,9,11-tetrahydroxy-3-pentyl  *Naphthacenes *Benzoquinones Glutathione Transferase/antagonists & inhibitors. J Antibiot (Tokyo) 1993 Aug;46(8):1309-11
bequinostatin C  152175-74-1 Benzo(a)naphthacene-2-carboxylic acid, 8,13-dihydro-1,7,9,11-tetrahydroxy-8,13-dioxo-3-pentyl  *Naphthacenes *Benzoquinones Glutathione Transferase/antagonists & inhibitors. J Antibiot (Tokyo) 1993 Aug;46(8):1309-11
5,6-11,12-bis(dithio)tetracene  0   *Disulfides *Naphthacenes. FEBS Lett 1993 Aug 23;329(1-2):205-9
bequinostatin B  151013-38-6   *Naphthacenes *Benzoquinones Glutathione Transferase/antagonists & inhibitors Streptomyces. J Antibiot (Tokyo) 1993 Jun;46(6):914-20
bequinostatin A  151013-37-5   *Naphthacenes *Benzoquinones Glutathione Transferase/antagonists & inhibitors Streptomyces. J Antibiot (Tokyo) 1993 Jun;46(6):914-20
benastatin D  150151-89-6 1,7,9,11-tetrahydroxy-5,6,8,13-tetrahydro-13,13-dimethyl-8-oxo-3-pentylbenzo(a)naphthacene  *Naphthacenes Glutathione Transferase/antagonists & inhibitors. J Antibiot (Tokyo) 1993 May;46(5):712-8
benastatin C  150151-88-5 8,13-dihydro-1,7,9,11-tetrahydroxy-8-oxo-13,13-dimethyl-3-pentylbenzo(a)naphthacene  *Naphthacenes Glutathione Transferase/antagonists & inhibitors. J Antibiot (Tokyo) 1993 May;46(5):712-8
5838 DNI  146864-75-7   *Naphthacenes. J Enzym Inhib 1992;6(2):157-64
aranciamycinone  95722-75-1   *Naphthacenes. Carbohydr Res 1992 Nov 4;235:141-9
desalaninebenanomicin A  145660-37-3   *Naphthacenes. J Antibiot (Tokyo) 1992 Oct;45(10):1645-52
benastatin B  138968-86-2 5,6,8,13-tetrahydro-1,7,9,11-tetrahydroxy-13,13-dimethyl-8-oxo-3-pentylbenzo(a)naphthacene-2-carboxylic acid  *Naphthacenes Glutathione Transferase/antagonists & inhibitors. J Antibiot (Tokyo) 1992 Sep;45(9):1391-6
benastatin A  138968-85-1 8,13-dihydro-1,7,9,11-tetrahydroxy-13-dimethyl-8-oxo-3-pentyl- benzo(a)naphthacene-2-carboxylic acid  *Naphthacenes Glutathione Transferase/antagonists & inhibitors. J Antibiot (Tokyo) 1992 Sep;45(9):1391-6
tetracenomycin X  121245-07-6 2-Naphthacenecarboxylic acid, 6,6a,7,10,10a,11-hexahydro-6a,7,12-trihydroxy-3,8,10a-trimethoxy-1-methyl-6,10,11-trioxo-, methyl ester, (6aR-(6aalpha,7alpha,10aalpha))  Naphthacenes. J Antibiot (Tokyo) 1989;42(4):640
tetracenomycin D3  117241-61-9 2-Naphthacenecarboxylic acid, 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-6,11-dioxo  Naphthacenes. J Antibiot (Tokyo) 1988;41(8):1066
tetracenomycin B3  117241-62-0 2-Naphthacenecarboxylic acid, 6,11-dihydro-3,10,12-trihydroxy-8-methoxy-1-methyl-6,11-dioxo  Naphthacenes. J Antibiot (Tokyo) 1988;41(8):1066
aklaviketone  116235-59-7   *Naphthacenes. J Antibiot (Tokyo) 1988;41(6):788
7-hydroxyadriamycin aglycone  0   *Naphthacenes. FEBS Lett 1988;234(1):199
SF 2446A1  115834-23-6   *Aminoglycosides *Naphthacenes. J Antibiot (Tokyo) 1988;41(4):425
galtamycinone  105997-04-4   *Glycosides *Naphthacenes. Antibiot Med Biotekhnol 1986;31(6):431
7-deoxyadriamycinol aglycone  37818-13-6   *Naphthacenes. Cancer Treat Rep 1986;70(5):619
7-deoxyadriamycin aglycone  38554-25-5   *Naphthacenes. Cancer Treat Rep 1986;70(5):619
4-O-(glucopyranosyl)-epsilon-rhodomycinone  62720-19-8   *Glycosides *Naphthacenes. J Antibiot (Tokyo) 1985;38(11):1622
bisanhydro-13-dihydrodaunomycinone  99260-72-7   *Naphthacenes. J Antibiot (Tokyo) 1985;38(9):1219
rubrene  517-51-1   *Naphthacenes. Prog Clin Biol Res 1984;170:563
beta-isorhodomycinone  80930-57-0   *Naphthacenes. J Antibiot (Tokyo) 1984;37(8):935
alpha(2)-rhodomycinone  18118-77-9 5,12-Naphthacenedione, 8-ethyl-7,8,9,10-tetrahydro-1,4,6,7,8,10-hexahydroxy-, (7R-(7alpha,8beta,10beta))  *Naphthacenes. J Antibiot (Tokyo) 1984;37(8):935
7-deoxy-13-dihydrodaunorubicinone  35994-55-9   *Naphthacenes. Z Allg Mikrobiol 1982;22(3):155
4'''-deoxy-4'''-aminoaclacinomycin  76439-76-4 1-Naphthacenecarboxylic acid, 4-((4-O-(4-O-((2S-(2alpha,5alpha,6beta))-5-aminotetrahydro-6-methyl-2H-pyran-2-yl)-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7  *Naphthacenes. J Antibiot (Tokyo) 1981;34(7):850
4'''-aclacinomycinamide  79391-09-6 1-Naphthacenecarboxylic acid, 4-((4-O-(4-O-((2S-(2alpha,5beta,6beta))-5-(acetylamino)tetrahydro-6-methyl-2H-pyran-2-yl)-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-2-ethyl-1,2,3,4,6,11-hexahydr  *Naphthacenes. J Antibiot (Tokyo) 1981;34(7):850
aklavinone  16234-96-1   Naphthacenes. J Antibiot (Tokyo) 1980;33(10):1199
tetracenomycin C  71135-22-3 2-Naphthacenecarboxylic acid, 6,6a,7,10,10a,11-hexahydro-6a,10a,12,?-tetrahydroxy-3,?-dimethoxy-1-methyl-6,11,?-trioxo-, methyl ester  Naphthacenes.
Pharma Action Anti-Bacterial Agents 		Arch Microbiol 121(2):111;1979
daunomycinone  21794-55-8   *Naphthacenes. Folia Microbiol (Praha) 24(2):117;1979
adriamycin aglycone  24385-10-2   *Naphthacenes. Biochem Med 12(3):283;1975

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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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