Quinazolinone

Last updated
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
PubChem CID
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 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).

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]

Contents

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

Related Research Articles

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<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Coordination complex</span> Molecule or ion containing ligands datively bonded to a central metallic atom

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<span class="mw-page-title-main">Functional group</span> Set of atoms in a molecule which augment its chemical and/or physical properties

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<span class="mw-page-title-main">Quinoline</span> Chemical compound

Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

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<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

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 that is soluble in water. Also known as 1,3-diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Though the parent quinazoline molecule is rarely mentioned by itself in technical literature, substituted derivatives have been synthesized for medicinal purposes such as antimalarial and anticancer agents. Quinazoline is a planar molecule. It is isomeric with the other diazanaphthalenes of the benzodiazine subgroup: cinnoline, quinoxaline, and phthalazine. Over 200 biologically active quinazoline and quinoline alkaloids are identified.

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Etaqualone is a quinazolinone-class GABAergic and is an analogue of methaqualone that was developed in the 1960s and marketed mainly in France and some other European countries. It has sedative, hypnotic, muscle relaxant and central nervous system depressant properties resulting from its agonist activity at the β-subtype of the GABAA receptor, and was used for the treatment of insomnia.

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<span class="mw-page-title-main">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

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References

  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.