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2-Quinolone

From Wikipedia, the free encyclopedia

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 InfoCard100.000.382Edit 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 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

2-Quinolone is anorganic compound related structurally toquinoline. It is the majoritytautomer in equilibrium with2-quinolinol. The compound can be classified as a cyclicamide, 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 ofacetoacetanilide.[3]

2-Quinolone (right) and itstautomer 2-hydroxyquinoline (left)

The isomer4-quinolone is the parent of a large class of antibiotics calledquinolone antibiotics. A prominent example isciprofloxacin, abroad spectrum antibiotic commonly used for treatment of various infections such asurinary tract infections (UTIs),typhoid,meningitis,gonorrhoea,syphilis,[4] andskin infections.[5]

References

[edit]
  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. Retrieved16 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. Retrieved8 February 2024.
  5. ^"About ciprofloxacin".nhs.uk. 14 December 2022. Retrieved8 February 2024.

External links

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