Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2013 Jun 3;7(1):95.
doi: 10.1186/1752-153X-7-95.

Quinazoline derivatives: synthesis and bioactivities

Dan Wang  1 , Feng Gao
Affiliations

Quinazoline derivatives: synthesis and bioactivities

Dan Wang et al. Chem Cent J. .

Abstract

Owing to the significant biological activities, quinazoline derivatives have drawn more and more attention in the synthesis and bioactivities research. This review summarizes the recent advances in the synthesis and biological activities investigations of quinazoline derivatives. According to the main method the authors adopted in their research design, those synthetic methods were divided into five main classifications, including Aza-reaction, Microwave-assisted reaction, Metal-mediated reaction, Ultrasound-promoted reaction and Phase-transfer catalysis reaction. The biological activities of the synthesized quinazoline derivatives also are discussed.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Synthesis of derivatives 3 by cascade imino-Diels-Alder reaction.
Scheme 2
Scheme 2
Synthesis of indolo[1,2-c]quinazolines 6 from azides 4.
Scheme 3
Scheme 3
Synthesis of 2-alkoxy-3H-quinazolin-4-ones.
Scheme 4
Scheme 4
Synthesis of 3H-quinazolin-4-ones via aza-Wittig reaction.
Scheme 5
Scheme 5
Synthesis of quinazoline compounds containing α-aminophosphonat.
Scheme 6
Scheme 6
Microwave-assisted one-pot synthesis of quinazoline compounds.
Scheme 7
Scheme 7
Solvent-catalyst-free microwave-assisted synthesis of quinazolines.
Scheme 8
Scheme 8
Synthesis of 3-benzimidazolyl-4(3H)-quinazolinones.
Scheme 9
Scheme 9
Synthesis of quinazolino[3,2-a]quinazolines.
Scheme 10
Scheme 10
Palladium-catalyzed one-pot synthesis of quinazolines.
Scheme 11
Scheme 11
Synthesis of imidazo[1,2-c]quinazoline derivatives.
Scheme 12
Scheme 12
TiCl4-Zn-mediated reduced synthesis of quinazoline derivatives.
Scheme 13
Scheme 13
Copper-catalyzed synthesis of indolo[1,2-c]quinazoline derivatives.
Scheme 14
Scheme 14
Copper-catalyzed one-pot synthesis of quinazolines derivatives.
Figure 1
Figure 1
Structures of palladium-copper co-catalyzed synthesis of quinazolines.
Scheme 15
Scheme 15
Ultrasound-assisted four-step synthesis of novel quinazoline derivatives.
Scheme 16
Scheme 16
PTC synthesis of alkylation quinazoline derivatives.
Scheme 17
Scheme 17
PTC synthesis of 4-alkylthio-quinazoline derivatives.
Figure 2
Figure 2
Structures of representative 4-substituted quinazolines with bioactivity.
Figure 3
Figure 3
Structures of representative heterocyclic quinazoline derivatives.
Figure 4
Figure 4
Structures of representative other quinazoline analogues.
See this image and copyright information in PMC

References

    1. Chandregowda V, Kush AK, Chandrasekara Reddy G. Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives. Eur J Med Chem. 2009;44:3046–3055. doi: 10.1016/j.ejmech.2008.07.023. - DOI - PubMed
    1. Al-Rashood ST, Aboldahab IA, Nagi MN, Abouzeid LA, Abdel-Aziz AA, Abdel-Hamide SG, Youssef KM, Al-Obaid AM, El-Subbagh HI. Synthesis, dihydrofolate reductase inhibition, antitumor testing, and molecular modeling study of some new 4(3H)-quinazolinone analogs. Bioorg Med Chem. 2006;14:8608–8621. doi: 10.1016/j.bmc.2006.08.030. - DOI - PubMed
    1. Vasdev N, Dorff PN, Gibbs AR, Nandanan E, Reid LM, Neil JPO’, VanBrocklin HF. Synthesis of 6-acrylamido-4-(2-[18F] fluoroanilino) quinazoline: A prospective irreversible EGFR binding probe. J Lablelled Compd Rad. 2005;48:109–115. doi: 10.1002/jlcr.903. - DOI
    1. Wakeling AE, Guy SP, Woodburn JR, Ashton SE, Curry BJ, Barker AJ, Gibson KH. ZD1839 (Iressa): an orally active inhibitor of epidermal growth factor signaling with potential for cancer therapy. Cancer Res. 2002;62:5749–5754. - PubMed
    1. Alagarsamy V, Solomon VR, Dhanabal K. Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H -quinazolin-4-one as analgesic, anti-inflammatory agents. Bioorg Med Chem. 2007;15:235–241. doi: 10.1016/j.bmc.2006.09.065. - DOI - PubMed