Quinazoline

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Quinazoline
Quinazoline numbering.png
Quinazoline molecule
Quinazoline molecule
Names
IUPAC name
Quinazoline
Other names
Benzopyrimidine, phenmiazine, benzo-1,3-diazine
Identifiers
253-82-7 YesY
ChEBI CHEBI:36621 YesY
ChEMBL ChEMBL301359 YesY
ChemSpider 8855 YesY
Jmol-3D images Image
PubChem 9210
Properties
C8H6N2
Molar mass 130.15 g·mol−1
Acidity (pKa) 3.51[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Quinazoline is a heterocyclic compound made up of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring. Its chemical formula is C8H6N2. Quinazoline is yellow solid. It is isomeric with other naphthyridines including quinoxaline, phthalazine and cinnoline. Derivatives of quinazoline are called quinazolines.

Medicinally it has been used in various areas especially as an anti-malarial agent and in cancer treatment. Quinazoline derivatives as quinazolinediones showed activity against murine P388 Leukemia, increased by dimerization.[2] One example of a compound containing the quinazoline structure is doxazosin mesylate.

The ring system is typically prepared by heating 2-acylanilides in the presence of ammonia or amines.[1]

See also[edit]

References[edit]

  1. ^ a b Armarego, W. L. F. (1963). "Quinazolines". Advances in Heterocyclic Chemistry 1: 253–309. doi:10.1016/S0065-2725(08)60527-9. ISBN 9780120206018. 
  2. ^ Giorgi-Renault, S., Renault J., Baron M., Gebel-Servolles, P., Delic, J., Cros S., Paoletti C., Heterocyclic quinones XIII. Dimerization in the series of 5,8-quinazolinediones: Synthesis and anti tumor effects of bis(4-amino-5,8-quinazolinediones), Chem. Pharm. Bull., 36 (10), 3933-3947 (1988).