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
CAS Number	59-31-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16365;
ChEMBL	ChEMBLCHEMBL186422;
ChemSpider	5816;
ECHA InfoCard	100.000.382
EC Number	200-420-6;
KEGG	C06338;
PubChem CID	6038;
UNII	803BHY7QWU;
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;
Properties
Chemical formula	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). 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.^[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

^ 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(1H)-Quinolinone". NIST. Retrieved 16 August 2023.
^ Lauer, W. M.; Kaslow, C. E. (1944). "4-Methylcarbostyril". Organic Syntheses. 24: 68. doi:10.15227/orgsyn.024.0068.
^ "Ciprofloxacin For The Treatment Of STDs: What You Need To Know | Allo Health". www.allohealth.care. 20 June 2023. Retrieved 8 February 2024.
^ "About ciprofloxacin". nhs.uk. 14 December 2022. Retrieved 8 February 2024.

External links

Media related to 2-Quinolone at Wikimedia Commons

[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.

[NIST59-31-4-2] "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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