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
. 2019 Mar 8;14(2):115-121.
doi: 10.4103/1735-5362.253358. eCollection 2019 Apr.

Synthesis of some novel dibromo-2-arylquinazolinone derivatives as cytotoxic agents

Zeinab Faghih  1 , Nasrin Rahmannejadi  1 , Razieh Sabet  2 , Kamiar Zomorodian  3 , Mohammad Asad  2 , Soghra Khabnadideh  1
Affiliations

Synthesis of some novel dibromo-2-arylquinazolinone derivatives as cytotoxic agents

Zeinab Faghih et al. Res Pharm Sci. .

Abstract

Recently the quinazoline derivatives have attracted much attention for their anticancer properties. In this study a series of new brominated quinazoline derivatives (1a-1g) were synthesized in two steps. In the first step we used N-bromosuccinimide to brominate the anthranilamid. Then in the second step we closed the quinazoline ring by different aromatic aldehydes. Our aldehydes contain different electron donating or electron withdrawing groups at different positions of the aromatic ring. The chemical structures of products were confirmed by spectroscopic methods such as IR, 1HNMR, 13CNMR, and mass spectroscopy. The cytotoxic activities of the compounds were assessed on three cancerous cell lines including MCF-7, A549, and SKOV3 using colorimetric MTT cytotoxic assay in comparison with cisplatin as a standard drug. Our results collectively indicated that 1f and 1g, exhibited the best anti-proliferative activities on three investigated cancerous cell lines.

Keywords: Anticancer; Cytotoxicity; MTT; Quinazolinone.

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Different quinazoline scaffolds
Scheme 1
Scheme 1
Synthesis of dibromo anthranilamide.
Scheme 2
Scheme 2
Synthesis of dibromo-2-arylquinazolinone (1a-1g).
See this image and copyright information in PMC

References

    1. Huang KH, Veal J, Barta T, Smith ED, Ma W, Ommen A. Quinazoline derivatives for the treatment of cancer. Google Patents EP3173084A1. 2010
    1. Arnold LD. 4-heterocyclyl-substituted quinazoline derivatives, processes for their preparation and their use as anti-cancer agents. Google Patents US5736534A. 1998
    1. Mertens AC, Yasui Y, Neglia JP, Potter JD, Nesbit ME, Jr, Ruccione K, et al. Late mortality experience in five-year survivors of childhood and adolescent cancer: the childhood cancer survivor study. J Clin Oncol. 2001;19(13):3163–3172. - PubMed
    1. DiMauro EF, Newcomb J, Nunes JJ, Bemis JE, Boucher C, Buchanan JL, et al. Discovery of aminoquinazolines as potent, orally bioavailable inhibitors of Lck: synthesis, SAR, and in vivo anti-inflammatory activity. J Med Chem. 2006;49(19):5671–5686. - PubMed
    1. Khan I, Ibrar A, Abbas N, Saeed A. Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: synthetic approaches and multifarious applications. Eur J Med Chem. 2014;76:193–244. - PubMed