Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives

El‐Badry, Yaser A.; Nassar, Ekhlass; El‐Hashash, M. A.

doi:10.5155/eurjchem.7.1.128-134.1370

Cited by 4 publications

(4 citation statements)

References 14 publications

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“…In this present work, nine compounds N-aryl-2-(2-methylquinazolin-4(3H)-yl)acetamides (4a−i) were successfully synthesized, and their structures were determined by IR, 1 H NMR, 13 C NMR, and HR-MS spectral analysis. This investigation also indicated that the acetamide compounds (4a−i) exhibited larvicidal activities against Aedes aegypti mosquito.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Quinazolin-4(3 H )-one is the basic skeleton found in many compounds having biological activity. Studies have shown that some compounds containing 2-methylquinazolin-4(3 H )-one heterocycle possess various biological effects such as antimicrobial, antifungal, anti-inflammatory, analgesic, and anticancer activities . Along with the quinazolin-4(3 H )-one nucleus, the acetamide component is also present in the structure of many biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

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Potential for Aedes aegypti Larval Control and Environmental Friendliness of the Compounds Containing 2-Methyl-3,4-dihydroquinazolin-4-one Heterocycle

Nguyen

Ngo

et al. 2023

ACS Omega

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2-Methylquinazolin-4(3H)-one was prepared by the reaction of anthranilic acid, acetic anhydride, and ammonium acetate. The reaction of 2-methylquinazolin-4(3H)-one with N-aryl-2-chloroacetamides in acetone in the presence of potassium carbonate gave nine N-aryl-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide compounds. The structures of these compounds were elucidated on the basis of their IR, 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high-resolution mass spectrometry (HR-MS) spectral data. These synthesized compounds containing the 2-methyl-3,4-dihydroquinazolin-4-one moiety exhibited activity against Aedes aegypti mosquito larvae with LC 50 values of 2.085−4.201 μg/mL after 72 h exposure, which is also confirmed using a quantitative structure−activity relationship (QSAR) model. Interestingly, these compounds did not exhibit toxicity to the nontarget organism Diplonychus rusticus. In silico molecular docking revealed acetylcholine binding protein (AChBP) and acetylcholinesterase (AChE) to be potential molecular targets. These data indicated the larvicidal potential and environmental friendliness of these Naryl-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide derivatives.

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Section: ■ Conclusionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Potential for Aedes aegypti Larval Control and Environmental Friendliness of the Compounds Containing 2-Methyl-3,4-dihydroquinazolin-4-one Heterocycle

Nguyen

Ngo

et al. 2023

ACS Omega

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“…[1][2][3][4][5][6][7] Moreover, cyclisation of above-mentioned hydrazides yielded substituted triazolo [c]quinazolines that show a wide range of biological activity including anticonvulsant, antitumor, hypoglycemic, antibacterial and other activities. [8][9][10][11][12][13][14][15][16][17][18][19][20][21] Despite the numerous publications devoted to the chemistry and biology of hydrazides formed by quinazolin-4(3H)-ylidenehydrazine, some features of their formation, reactivity, physicochemical and biological properties have been insufficiently studied. One of the promising directions of studies is the synthesis and further cyclization of hydrazides formed by quinazolin-4(3H)-ylidenehydrazine and dicarboxylic acids or their monoesters.…”

Section: Introductionmentioning

confidence: 99%

Quinazoline-containing Hydrazydes of Dicarboxylic Acids and Products of Their Structural Modification: A Novel Class of Anti-inflammatory Agents

Красовська

Stavytskyi

Носуленко

et al. 2021

ACSi

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The synthesis of hydrazides formed by quinazolin-4(3H)-ylidenehydrazine and dicarboxylic acids, as well as their further modification are described in the present manuscript. It was shown that above-mentioned hydrazides may be obtained via acylation of initial quinazolin-4(3H)-ylidenehydrazine by corresponding acylhalides, cyclic anhydrides and imidazolides of dicarboxylic acids monoesters. Obtained hydrazides were converted into [1,2,4]triazolo[1,5-с]quinazolines that were used as initial compounds for chemical modification aimed to the introduction of amide fragment to the molecule. The IR, 1H NMR and chromato-mass spectral data of obtained compounds were studied and discussed. Obtained substances were studied for anti-inflammatory activity using carrageenan-induced paw inflammation model. Amides of ([1,2,4]triazolo[1,5-с]quinazoline-2-yl)alkyl carboxylic acids were detected as promising class of anti-inflammatory agents for further purposeful synthesis and profound study of anti-inflammatory activity.

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“…The improvement of promising therapeutic agents for the controlling microorganisms has undergone continual domination to the evolution of more adequate classes of drugs. In continuation of our program [14][15][16][17][18] , the present work will explore a novel series of quinazolinones. Derivatives of attractive quinazolinoneswill be synthesized and characterized with the aim obtaining a source of functionalized molecules.…”

Section: Introductionmentioning

confidence: 99%

Construction of Some Novel Biocidal N-Alkylated Quinazoline-4(3h)- One Derivatives Using Microwave Activation

El‐Badry¹,

Abdou²

2018

PTQ

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Microwave-assisted construction of 2-propylquinazolinone1 has been achieved, followed by its subsequent utilities in constructing an attractive series of 2,3-disubstituted functional quinazolinones 2-10. The use of microwave irradiation in performing N-alkylation for the titled quinazolinone 1 was applied as a simple, efficient and eco-friendly green technique. Furthermore, the in vitro antimicrobial screening of the obtained compounds 3-10 has been investigated against four bacterial strains and two fungal strains. The structure of the synthesized molecules was affirmed using analytical and spectral tools.

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Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives

Cited by 4 publications

References 14 publications

Potential for Aedes aegypti Larval Control and Environmental Friendliness of the Compounds Containing 2-Methyl-3,4-dihydroquinazolin-4-one Heterocycle

Potential for Aedes aegypti Larval Control and Environmental Friendliness of the Compounds Containing 2-Methyl-3,4-dihydroquinazolin-4-one Heterocycle

Quinazoline-containing Hydrazydes of Dicarboxylic Acids and Products of Their Structural Modification: A Novel Class of Anti-inflammatory Agents

Construction of Some Novel Biocidal N-Alkylated Quinazoline-4(3h)- One Derivatives Using Microwave Activation

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