2-Quinolone

2-Quinolone
Names
Preferred IUPAC name
Quinolin-2(1H)-one
Other names
  • Carbostyril
  • 1,2-Dihydro-2-oxoquinoline
  • 1H-Quinolin-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.382 Edit this at Wikidata
EC Number
  • 200-420-6
KEGG
UNII
  • 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
  • C1=CC=C2C(=C1)C=CC(=O)N2
Properties
C9H7NO
Molar mass 145.161 g·mol−1
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 [77 °F], 100 kPa).

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.[1][2] The 4-methyl-2-quinolone can be prepared by dehydration of acetoacetanilide.[3]

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,[4] and skin infections.[5]

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.

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