Method Optimization for Synthesis of Trisubstitued Quinazoline Derivatives

Haghighijoo, Zahra; Eskandari, Masoomeh; Khabnadideh, Soghra

doi:10.18103/mra.v5i5.1199

Cited by 4 publications

(3 citation statements)

References 9 publications

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“…All new synthesized compounds were chose from our previous study( 13 14 ). A brief of general procedure for synthesis and their chemical structures are mentioned here.…”

Section: Methodsmentioning

confidence: 99%

Structure based design and anti-breast cancer evaluation of some novel 4-anilinoquinazoline derivatives as potential epidermal growth factor receptor inhibitors

et al. 2018

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Quinazoline is one of the most widespread scaffolds amongst natural and synthetic bioactive compounds. Recently the quinazoline derivatives and in particular the 4-anilinoquinazolines have attracted much attention for their anticancer properties due to their capability to stabilize the kinase activity of epidermal growth factor receptor (EGFR). A series of fifteen previously designed and synthesized 4-anilinoquinazoline analogs (4-18) were evaluated for cytotoxic activity on two breast cancer cell lines (MCF-7 and MDA-MB-468). Ligand efficiency and binding mode studies were also done and evaluated for their potentially EGFR inhibitory effects in comparison with imatinib and erlotinib as reference drugs. Among the tested 4-anilinoquinazolines, compound 11, which contains diethoxy at phenyl ring and morpholino pendants at positions 5 and 7 of the quinazoline ring, demonstrated the most potent biological activity on both cell lines. Our new quinazoline derivatives with different substituents such as cyclic or linear ethers and flour groups may be a promising cytotoxic lead compounds for further anti-breast cancer research.

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“…All new synthesized compounds were chose from our previous study( 13 14 ). A brief of general procedure for synthesis and their chemical structures are mentioned here.…”

Section: Methodsmentioning

confidence: 99%

Structure based design and anti-breast cancer evaluation of some novel 4-anilinoquinazoline derivatives as potential epidermal growth factor receptor inhibitors

et al. 2018

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“…Te results showed that the substitution type on the phenyl ring of anthranilic acid and also various anilines with diferent substituents had negligible efects on the reaction yield. Tis method has some advantages like good yield of products, cleaner products, and easy work up [37,38].…”

Section: 27mentioning

confidence: 99%

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

Khabnadideh

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.

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“…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

Khabnadideh

2020

Journal of Heterocyclic Chem

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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.

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Method Optimization for Synthesis of Trisubstitued Quinazoline Derivatives

Cited by 4 publications

References 9 publications

Structure based design and anti-breast cancer evaluation of some novel 4-anilinoquinazoline derivatives as potential epidermal growth factor receptor inhibitors

Structure based design and anti-breast cancer evaluation of some novel 4-anilinoquinazoline derivatives as potential epidermal growth factor receptor inhibitors

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

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

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