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Quinazolinone

From Wikipedia, the free encyclopedia
4-Quinazolinone
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
  • InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)
  • O=C2\N=C/Nc1ccccc12
Properties
C8H6N2O
Molar mass146.149 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Quinazolinone is aheterocyclic chemical compound, aquinazoline with acarbonyl group in the C4N2 ring. Twoisomers are possible: 2-quinazolinone and 4-quinazolinone, with the 4-isomer being the more common. These compounds are of interest inmedicinal chemistry.[1]

  • 2-Quinazolinone
    2-Quinazolinone
  • 4-Quinazolinone
    4-Quinazolinone

Synthesis

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

Derivatives

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

See also

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References

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  1. ^Jafari, E; et al. (2016), "Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities",Res Pharm Sci,11 (1):1–14,PMC 4794932,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.
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Retrieved from "https://en.wikipedia.org/w/index.php?title=Quinazolinone&oldid=1329688838"
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