Synthesis and antitumor activities of novel bis‐quinazolin‐4(3H)‐ones

Abstract

With the aim of obtaining new antitumor agents, a series of bis‐quinazolin‐4(3H)‐ones (3a‐3 f) were designed and synthesized. These products contain 4‐oxo‐1,2,3,4‐tetrahydro‐quinazoline and 3H‐quinazolin‐4‐one moieties linked together via a propyl chain. Cytotoxic activities of 3a‐3 f were evaluated against lung adenocarcinoma (A549), breast carcinoma (MCF‐7) and ovarian cancer (SKOV3) cell lines using MTT method. Cisplatin was used as a positive control. Among the tested compounds 3a, 3b, and 3e showed the best cytotoxic activities against all cancerous cell lines with IC50 values even less than cisplatin. Compounds 3d and 3f also showed desirable cytotoxic activities especially against A549 and MCF‐7.

New Diacetic Acids Containing Quinazolin‐4(3H)‐one: Synthesis, Characterization, Anticholinergic Properties, DFT Analysis and Molecular Docking Studies

“…The accessibility of 4(3H) derivatives and the versatility of their biological activities attract attention to this class of compounds. In the last three decades, many studies have been conducted on the anticancer, [12,13] antimicrobial and antifungal, [14] antiinflammatory, [15] antioxidant, [16] anticonvulsant, [17] antitumor, [18] antileishmanial, [19] antihistaminic, [20] antiviral, [21] anticholinergic [22,23] and antidiabetic [24,25] properties of quinazolinones.…”

Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry

“…Rahmannejadi et al [31] synthesized a very new series of bis-quinazolin-4(3H)-ones derivatives and evaluated them for their antitumor activity. Bromo derivatives of this compound were found to have the maximum potential of cytotoxic activity over dibromo or dimethyl compounds.…”

6‐Bromoquinazoline Derivatives as Potent Anticancer Agents: Synthesis, Cytotoxic Evaluation, and Computational Studies

“…According to these findings, developing of biologically active quinazoline analogs and their structural modifications are interesting research topics in our group. We previously, designed synthetic methods to prepare potent quinazoline derivatives and also, screened them for their biological activities [17–19] . In addition, we recently reported synthesis of some potent dibromoquinazoline [20] and 2‐(Chloromethyl)‐3‐phenylquinazolin‐4(3H)‐one derivatives [21] which bearing bromine group on phenyl ring and attached chlorin group with a carbon spacer at N3 position of their quinazolinone ring, respectively.…”

“…We previously, designed synthetic methods to prepare potent quinazoline derivatives and also, screened them for their biological activities. [17][18][19] In addition, we recently reported synthesis of some potent dibromoquinazoline [20] and 2-(Chloromethyl)-3phenylquinazolin-4(3H)-one derivatives [21] which bearing bromine group on phenyl ring and attached chlorin group with a carbon spacer at N3 position of their quinazolinone ring, respectively. Interestingly, these modified quinazoline scaffolds were active compounds against lung, breast and colon cancer cell lines.…”