Quinazolinone is a
heterocyclic
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
chemical compound, a
quinazoline
Quinazoline is an organic compound with the formula C8H6N2. It is an aromatic heterocycle with a bicyclic structure consisting of two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring. It is a light yellow crystalline solid ...
with a
carbonyl group
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
in the C
4N
2 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
Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with designing and developing pharmaceutical drugs. Medicinal chemistry involves the identification, synthesis and developme ...
.
Synthesis
Common routes to quinazolines involve condensation of
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...
s to anilines with ortho nitrile, carboxylic acids and amides.
Quinazolinone drugs that function as
hypnotic/
sedatives usually contain a 4-quinazolinone core with a 2-substituted
phenyl group at nitrogen atom 3.
See also
*
Idelalisib (Zydelig)
*
Methaqualone
Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude ( ) and Sopor among others, which contained 300 mg of methaqualone, and sold as a combination drug under the brand name Mandrax, which contained 250 mg me ...
(Quaalude)
*
Cloroqualone
*
SL-164 (Dicloqualone)
*
Diproqualone
Diproqualone is a quinazolinone class GABAergic and is an analogue of methaqualone developed in the late 1950s by a team at Nogentaise de Produits Chimique. It was marketed primarily in France and some other European countries. It has sedative ...
*
Etaqualone
*
Mebroqualone
*
Mecloqualone
*
Methylmethaqualone
*
Nitromethaqualone
References
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