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Quinalizarin

From Wikipedia, the free encyclopedia
Quinalizarin
Skeletal formula of quinalizarin
Skeletal formula of quinalizarin
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
1,2,5,8-Tetrahydroxyanthracene-9,10-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.001.243Edit this at Wikidata
UNII
  • InChI=1S/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H ☒N
    Key: VBHKTXLEJZIDJF-UHFFFAOYSA-N ☒N
  • InChI=1/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H
    Key: VBHKTXLEJZIDJF-UHFFFAOYAM
  • C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O
Properties
C14H8O6
Molar mass272.212 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound
Not to be confused with quinizarin, adihydroxyanthraquinone.

Quinalizarin or1,2,5,8-tetrahydroxyanthraquinone is anorganic compound with formulaC12H4(OH)4(CO)2. It is one of manytetrahydroxyanthraquinone isomers, formally derived fromanthraquinone by replacement of fourhydrogen atoms byhydroxyl (OH) groups at the 1, 2, 5, and 8 positions.

Quinalizarin is an inhibitor of theenzymeprotein kinase CK2. It is more potent and selective thanemodin.[1] It is also a potentcatechol O-methyltransferase (COMT) inhibitor.[2][3]

See also

[edit]

References

[edit]
  1. ^Cozza, G.; Mazzorana, M.; Papinutto, E.; Bain, J.; Elliott, M.; di Maira, G.; Gianoncelli, A.; Pagano, M. A.; Sarno, S.; Ruzzene, M.; Battistutta, R.; Meggio, F.; Moro, S.; Zagotto, G.; Pinna, L. A. (2009)."Quinalizarin as a Potent, Selective and Cell-Permeable Inhibitor of Protein Kinase CK2"(PDF).The Biochemical Journal.421 (3):387–395.doi:10.1042/BJ20090069.hdl:2262/45362.PMID 19432557.
  2. ^Schneider J, Huh MM, Bradlow HL, Fishman J (April 1984)."Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells".J. Biol. Chem.259 (8):4840–5.doi:10.1016/S0021-9258(17)42922-X.PMID 6325410.
  3. ^Schütze N, Vollmer G, Knuppen R (April 1994). "Catecholestrogens are agonists of estrogen receptor dependent gene expression in MCF-7 cells".J. Steroid Biochem. Mol. Biol.48 (5–6):453–61.doi:10.1016/0960-0760(94)90193-7.PMID 8180106.


Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase


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