Synthesis, docking, and cytotoxic activities of novel 2-aryl-4-(arylamino)quinazolines

Sadeghian

2022

Journal of Chemistry

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Quinazoline scaffold and its various derivatives, as an important category of heterocyclic compounds, have received much attention for the design and development of new drugs due to their various pharmacological properties like anticancer, anticonvulsant, antidepressant, antibacterial, antifungal, antioxidant, anti-HIV, antileishmanial, anticoccidial, antimalarial, anti-inflammatory, antileukemic, and antimutagenic. Among the various substituted quinazolines, 4-aminoquinazoline scaffold, as a privileged structure in medicinal chemistry, is present in many approved drugs and biologically active compounds. Furthermore, 4-aminoquinazoline derivatives are often applied as key intermediates in the preparation of bioactive compounds. The current review focuses on the key methods for the preparation of 4-aminoquinazoline derivatives, including the nucleophilic substitution reaction, metal-catalyzed approaches, microwave irradiation methods, cyclocondensation, and direct amination methods.

Section: Solid-phase Methodmentioning

confidence: 99%

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

Sadeghian

2022

Journal of Chemistry

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“…Among the nitrogen-containing compounds, the quinazoline ring was a very privileged and effective scaffold in pharmaceutical and medicinal chemistry; they have a broad spectrum of biological activities such as anticancer, diuretic, anti-inflammatory, anticonvulsant, antimicrobial, antiviral, antiplasmodial, and antihypertensive effects ( 1 ). Also, among the different quinazoline scaffolds, 2-substituted-4(3H)-quinazolinone has been used as an attractive pharmacophore for drug design purposes ( 2 3 ). Quinazoline which is substituted at C4, C6, and C7 has been applied as one of the most significant classes of quinazoline-based epidermal growth factor receptor (EGFR) inhibitors ( 4 ).…”

Section: Introductionmentioning

confidence: 99%

Quinazoline analogues as cytotoxic agents; QSAR, docking, and in silico studies

Emami

Sabet

Research in Pharmaceutical Sciences

et al. 2021

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Background and purpose: Synthesis and investigation of pharmacological activity of novel compounds are time and money-consuming. However, computational techniques, docking, and in silico studies have facilitated drug discovery research to design pharmacologically effective compounds. Experimental approach: In this study, a series of quinazoline derivatives were applied to quantitative structure-activity relationship (QSAR) analysis. A collection of chemometric methods were conducted to provide relations between structural features and cytotoxic activity of a variety of quinazoline derivatives against breast cancer cell line. An in silico -screening was accomplished and new impressive lead compounds were designed to target the epidermal growth factor receptor (EGFR)-active site based on a new structural pattern. Molecular docking was performed to delve into the interactions, free binding energy, and molecular binding mode of the compounds against the EGFR target. Findings/Results: A comparison between different methods significantly indicated that genetic algorithm-partial least-squares were selected as the best model for quinazoline derivatives. In the current study, constitutional, functional, chemical, resource description framework, 2D autocorrelation, and charge descriptors were considered as significant parameters for the prediction of anticancer activity of quinazoline derivatives. In silico screening was employed to discover new compounds with good potential as anticancer agents and suggested to be synthesized. Also, the binding energy of docking simulation showed desired correlation with QSAR and experimental data. Conclusion and implications: The results showed good accordance between binding energy and QSAR results. Compounds Q 1 -Q 30 are desired to be synthesized and applied to in vitro evaluation.

“…In vitro anticancer activity of some biquinazoline-2,2′-diones was also studied by Dou and co-workers. [16] To continue our previous researches [17][18][19][20][21][22] here we decided to synthesize some bis-quinazolines and evaluate their cytotoxic properties against cancer. A549 as an invasive lung cancer cell line provide a useful tool for the study of biological properties of lung cancer in vitro.…”

Section: Introductionmentioning

confidence: 99%

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

Rahmannejadi

Yavari

Journal of Heterocyclic Chem

2020

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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.