Chemistry:Quinazolinone

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4-Quinazolinone
4-Quinazolinone.png
Names
Preferred IUPAC name
Quinazolin-4(3H)-one
Other names
4(3H)-Quinazolinone; 4(1H)-Quinazolinone; 3,4-Dihydroquinazolin-4-one; 4(3H)-Quinazolone; 4-Hydroxyquinazoline; 4-Oxo-3,4-dihydroquinazoline; 4-Oxoquinazoline; 4-Quinazolinol; 4-Quinazolinone; 4-Quinazolone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
Properties
C8H6N2O
Molar mass 146.149 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Quinazolinone is a heterocyclic chemical compound, a quinazoline with a carbonyl group in the C4N2 ring. Two isomers are possible: 2-quinazolinone and 4-quinazolinone, with the 4-isomer being the more common. These compounds are of interest in medicinal chemistry.[1]

Synthesis

Common routes to quinazolines involve condensation of amides to anilines with ortho nitrile, carboxylic acids and amides.[2]

Quinazolinone drugs that function as hypnotic/sedatives, methaqualone (Quaalude) for example, usually contain a 4-quinazolinone core with a 2-substituted phenyl group at nitrogen atom 3.

See also

References

  1. Jafari, E (2016), "Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities", Res Pharm Sci 11 (1): 1–14, PMID 27051427. 
  2. Connolly, David J.; Cusack, Declan; O'Sullivan, Timothy P.; Guiry, Patrick J. (2005). "Synthesis of quinazolinones and quinazolines". Tetrahedron 61 (43): 10153–10202. doi:10.1016/j.tet.2005.07.010.