Microwave-assisted one-pot syntheses of 4-aminoquinazolines

Song, Wenting; He, Shunli; Yuan, Zeli; Yu, Guangqing; Wu, Di; Wu, Qing; Min-qing, Zhang; Chen, Yongzheng; Hu, Qinghong

doi:10.1515/gps-2015-0121

Cited by 3 publications

(3 citation statements)

References 32 publications

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“…Ten, aromatization and elimination of the dimethylamino moiety leads to the expected product 112. Te advantages of this procedure are simple, one-pot cascade, short reaction time, environmentally friendly, and low volume of the organic solvent [36].…”

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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Section: 27mentioning

confidence: 99%

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

Khabnadideh

Sadeghian

2022

Journal of Chemistry

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“…Compounds 1-3 and 4-bis (2-chloroethyl) aminobenzaldehyde were prepared as described in our previous study (Song et al, 2016). All chemical reagents and solvents were purchased from the J&K Scientific Ltd and Energy chemical company, and without further purification.…”

Section: Synthesis Of Compounds I-iiimentioning

confidence: 99%

“…The synthesis of target compounds I~III was outlined in Figure 1. In brief, starting materials 1~3 were efficiently synthesized using microwave irradiation in our previous study (Song et al, 2016). Next, the nitro groups of 1~3 were reduced via disposing with Pd/C-hydrazine hydrate or Fe/acetic acid to give key intermediates 4~6.…”

Section: Synthesis Of Compound I~iiimentioning

confidence: 99%

Synthesis of a New Phenyl Chlormethine-Quinazoline Derivative, a Potential Anti-Cancer Agent, Induced Apoptosis in Hepatocellular Carcinoma Through Mediating Sirt1/Caspase 3 Signaling Pathway

Song

et al. 2020

Front. Pharmacol.

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Quinazoline derivatives display multiple pharmacological activities and target various biological receptors. Based on the skeleton of quinazoline core, we designed and synthesized three new quinazoline-phenyl chlormethine conjugates (I-III) bearing a Schiff base (C = N) linker, and investigated their anti-tumor effects on HepG2-xenografted tumor and human cancer cell line HepG2. Among these compounds, compound II showed better inhibitory effect against HepG2 cells. In the present study, TUNEL staining, western blot, molecular docking, and siRNA were used to investigate the inhibitory mechanism of compound II towards hepatoma. Compound II inhibited HepG2-xenografted tumor growth in nude mice. Moreover, Compound II not only up-regulated Bax/Bcl-2 ratio and active-caspase 3 level, but also down-regulated Sirt1 expression and its activity, as well as PGC-1a expression. Furthermore, compound II also significantly suppressed the promotion of HepG2 cell proliferation, as evidenced by MTT assay and lactate dehydrogenase (LDH) release assay. Of note, the cytotoxicity of Compound II on HepG2 cells mainly via regulating Sirt1/caspase 3 signaling pathway, consisting with the results in vivo. Intriguingly, z-DEVD-FMK, a caspase 3 inhibitor, almost abolished the inhibitory effects of compound II. Of note, knockdown of caspase 3 by siRNA significantly reversed the inhibitory effect of compound II on HepG2. Interestingly, compound II directly bonded to Sirt1, indicating that Sirt1 might be a promising therapeutic target of compound II. In summary, our findings reveal that compound II, a new synthetical phenyl chlormethine-quinazoline derivative, contributes to the apoptosis of HepG2 cells both in vivo and in vitro through mediating Sirt1/caspase 3 singling pathway. These findings demonstrate that compound II may be a new potent agent against hepatocellular carcinoma.

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A spirobenzopyran-based multifunctional chemosensor for the chromogenic sensing of Cu2+ and fluorescent sensing of hydrazine with practical applications

Cao

et al. 2017

Sensors and Actuators B: Chemical

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Microwave-assisted one-pot syntheses of 4-aminoquinazolines

Abstract: A simple, environmentally friendly, one-pot method for the synthesis of 4-aminoquinazolines using microwave irradiation has been developed. Structures of derivatives

Cited by 3 publications

References 32 publications

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

Synthesis of a New Phenyl Chlormethine-Quinazoline Derivative, a Potential Anti-Cancer Agent, Induced Apoptosis in Hepatocellular Carcinoma Through Mediating Sirt1/Caspase 3 Signaling Pathway

A spirobenzopyran-based multifunctional chemosensor for the chromogenic sensing of Cu2+ and fluorescent sensing of hydrazine with practical applications

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