2-Quinolone

2-Quinolone

2-Quinolone

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

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

Quick Facts Names, Identifiers ...

The isomer 4-quinolone is the parent of a large class of antibiotics called quinolone antibiotics. An 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. [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]
    "2(1H)-Quinolinone". NIST. Retrieved 16 August 2023.
  3. [3]
    Lauer, W. M.; Kaslow, C. E. (1944). "4-Methylcarbostyril". Organic Syntheses. 24: 68. doi:10.15227/orgsyn.024.0068.
  4. [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. [5]
    "About ciprofloxacin". nhs.uk. 14 December 2022. Retrieved 8 February 2024.
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