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2-Quinolone


Column 1Column 2
Preferred IUPAC name
Quinolin-2(1H)-one
Other names
Carbostyril1,2-Dihydro-2-oxoquinoline1H-Quinolin-2-one
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}59-31-4
3D model (JSmol)Interactive image
ChEBICHEBI:16365
ChEMBLChEMBLCHEMBL186422
ChemSpider5816
ECHA InfoCard100.000.382
EC Number200-420-6
KEGGC06338
PubChem CID6038
UNII803BHY7QWU
CompTox Dashboard (EPA)DTXSID1058769
InChI
InChI=1S/C9H7NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H,(H,10,11)Key: LISFMEBWQUVKPJ-UHFFFAOYSA-N
SMILES
C1=CC=C2C(=C1)C=CC(=O)N2
Chemical formulaC9H7NO
Molar mass145.161 g·mol−1
Appearancesolid
Melting point199.5 °C (391.1 °F; 472.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references | |

2-Quinolone is an organic compound related structurally to quinoline. It is the majority tautomer in equilibrium with 2-quinolinol. The compound can be classified as a cyclic amide, and as such is used as an isostere for peptides and other pharmaceutically inspired targets. The 4-methyl-2-quinolone can be prepared by dehydration of acetoacetanilide.

2-Quinolone (right) and its tautomer 2-hydroxyquinoline (left)

The isomer 4-quinolone is the parent of a large class of antibiotics called quinolone antibiotics. A prominent example is ciprofloxacin, a broad spectrum antibiotic commonly used for treatment of various infections such as urinary tract infections (UTIs), typhoid, meningitis, gonorrhoea, syphilis, and skin infections.

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