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2-Quinolone

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(Redirected from Carbostyril)

2-Quinolone
Names
Preferred IUPAC name Quinolin-2(1H)-one
Other names
  • Carbostyril
  • 1,2-Dihydro-2-oxoquinoline
  • 1H-Quinolin-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.382 Edit this at Wikidata
EC Number
  • 200-420-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Properties
Chemical formula C9H7NO
Molar mass 145.161 g·mol
Appearance solid
Melting point 199.5 °C (391.1 °F; 472.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

References

  1. Tashima, Toshihiko (2015). "The structural use of carbostyril in physiologically active substances". Bioorganic & Medicinal Chemistry Letters. 25 (17): 3415–3419. doi:10.1016/j.bmcl.2015.06.027. PMID 26112444.
  2. "2(1H)-Quinolinone". NIST. Retrieved 16 August 2023.
  3. Lauer, W. M.; Kaslow, C. E. (1944). "4-Methylcarbostyril". Organic Syntheses. 24: 68. doi:10.15227/orgsyn.024.0068.
  4. "Ciprofloxacin For The Treatment Of STDs: What You Need To Know | Allo Health". www.allohealth.care. 20 June 2023. Retrieved 8 February 2024.
  5. "About ciprofloxacin". nhs.uk. 14 December 2022. Retrieved 8 February 2024.

External links

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