Effects of the Substituent at C-2 Phenyl on the <i>N-/O</i>-Alkylation of Quinazolin-4(3<i>H</i>)-one and Anti-Tumor, Antimicrobial Activities of Some Compounds

王淑霞,; 高梦颖,; 谭官海,; 马海霞,; 赵莹莹,; 杜鸿源,; 王总帅,; 陈华,; 李小六,

doi:10.6023/cjoc201608031

Cited by 6 publications

(1 citation statement)

References 6 publications

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“…Quinazolinone derivatives have been attracting growing attention from medicinal and agricultural chemists, owing to their diverse biological activities, such as antibacterial [21][22][23][24][25][26][27], antifungal [28][29][30], antiviral [31,32], antitumor [33,34] and anticonvulsant [35] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis And Antibacterial Activity of 6-Bromo-2-(O-Aminophenyl)-3-Amino-Quinazolin-4(3h)-One From 6-Bromo,2-(O-Aminophenyl)-3,1-Benzoxazin-4(3h)-One

Osarodion

2023

CCRT

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Introduction: Quinazolinone derivatives reveal various medicinal properties such as analgesic, anti-inflammatory and anticancer activities, as well as antimicrobial activity. These heterocycles are valuable intermediates in organic synthesis.Methods/Experimental: The compound, 6-bromo,2-(o-aminophenyl)-3,1-benzoxazin-4(3H)-one (1) was synthesized by dissolving 5-bromo anthranillic acid in 100 ml of pyridine. To this reaction mixture o-amino benzoyl chloride stirring at room temperature for 30 minutes this was refluxed with 75 mL of hydrazine hydrate for 3 hrs at 120-1300C. the reaction mixture was allowed to cool to room temperature to give 6-bromo-2-(o-aminophenyl)-3-amino-Quinazolin-4(3H)-one (2). These Compounds were evaluated for their bacterialrial activity (against some gram positive and gram negative microorganism) and antifungal activity (against Candida albicans). Study Design: This study was experimentally design and the antibacterial activity was evaluated against some microorganism, Staphylococcus aureus, Bacillus species, Aspergillus Species, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, and candida albicans Result: The compounds exhibited significant antibacterial activity with a zone of inhibition in the range of 10 – 16mm in comparison to control. Conclusions: From our findings, the compounds synthesized have higher antibacterial activities as compared to Ciprofloxicin (CPX) and Ketonaxol (PEF) standard antibacterial drugs.

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Section: Introductionmentioning

confidence: 99%

Synthesis And Antibacterial Activity of 6-Bromo-2-(O-Aminophenyl)-3-Amino-Quinazolin-4(3h)-One From 6-Bromo,2-(O-Aminophenyl)-3,1-Benzoxazin-4(3h)-One

Osarodion

2023

CCRT

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Efficient Synthesis of Quinazolinones by Transition‐Metal‐Free Direct Aerobic Oxidative Cascade Annulation of Alcohols witho‐Aminoarylnitriles

Wang

Liu

et al. 2019

ChemSusChem

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Am ild and atom-economic method was developed for direct and efficient synthesis of quinazolinones through at ransitionmetal-free aerobic oxidativec ascade annulation reaction of widely available o-aminoarylnitriles and alcohols. Air could be employeda sa ne ffective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the "cesium effect", the water-soluble base CsOH was found to be crucial in all key steps of the reactionm echanism.B ecause a wide range of substrates can be used to prepare substituted quinazolinones withoutc ontamination by transition-metal residues, this method mayb eo fi nterestf or application in pharmaceutical synthesis. Possible reaction paths were also proposed according to controlr eactions.Heterocycle derivatives have broad applications in many fields, especially the organic,p harmaceutical, and natural product synthesis, agrochemistry,m aterials, and life sciences. For example, the quinazolinone motif and derivatives are abundant in numerous synthetic compoundsa nd natural alkaloids with diverse biological and pharmacological activities such as antimalarial, antimicrobial, anti-inflammatory,a nticonvulsant, antihypertensive, anti-diabetic, anticancer,a ntitumor, cholinesteraseinhibitory, dihydrofolate reductase-inhibitory,a nd kinase-inhibitory properties. [1,2] Hence, av ariety of methods have been developedf or quinazolinones keleton construction. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Among the methods reported, annulation reactions of o-aminoaryl acids and derivatives may be the most employed strategies, which include the condensation of o-aminoaryl acids with amides, nitriles, or acidd erivatives with an itrogen source (Scheme 1A), [2,3] the dehydrogenative or oxidative annulation of o-aminoarylamides with aldehydes, [4] masked aldehydes, [5] ketones, [6] imines, [7] or amines [8] (Scheme 1B), the carbonylative annulation of o-aminoarylamides with aC Os ource and aryl halides( Scheme 1C), [9] and the annulation of o-aminoarylnitriles with acid derivatives, [10] aldehydes, [11] or ketones [12] (Scheme 1D). Moreover, transition-metal-catalyzed coupling reactions of o-haloarylamides with amides, nitriles, amines,o ra ldehydee quivalents with an itrogen source (Scheme 1E) [13] as well as other annulation reactions [2,14] have also received much attention recently.A lcohols are known as ac lass of greener, more available, more economic, more stable, and less toxic chemicals. [15] Therefore, the use of alcohols instead of the Scheme1.Generalmethods for quinazolinone skeleton construction.[a] Q.

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Design, Synthesis, Characterization, and Antimicrobial Properties of New Azo Disperse Dyes Incorporating Quinazolinone-Pyrazolone Moieties and Their Applications for Dyeing of Polyester Fabrics

Ibrahim,

Selim,

Sakr

et al. 2024

Fibers Polym

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The current study outlines a straightforward and efficient method for creating new quinazolinone disperse dyes based on pyrazolone moieties, starting with quinazolinone and a variety of substituted pyrazolone as couplers. The synthesized dyes were characterized using a variety of spectroscopic and analytical methods. The synthesized dyes' ultraviolet–visible spectra showed bands brought on by several molecular transitions. We investigated in detail the multifunctional characteristics such color representation, dyeing duration, concentration, pH, buildup, and fastness properties of the dyed samples. Fastness properties and colorimetric data showed satisfactory results, demonstrating the effectiveness of these dyes in dyeing polyester fabrics. A pH of 5 and a dyeing temperature of 130 °C were the ideal conditions for dyeing polyester fabrics. Additionally, an ultraviolet protection factor test was performed on the dyed fabrics, and the results showed that these dyes provide the best UV protection. These dyes are suitable for industrial dyeing applications since they are easy to manufacture and scale up. Additionally, in-vitro testing was done to determine the dyes' antibacterial effectiveness against various bacteria and fungi. The antibacterial activity of the dyes was moderate to very good against both Gram-positive and Gram-negative bacteria, as well as fungi.

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Effects of the Substituent at C-2 Phenyl on the N-/O-Alkylation of Quinazolin-4(3H)-one and Anti-Tumor, Antimicrobial Activities of Some Compounds

Abstract: (50 µg/mL)对大肠杆菌和痢疾杆菌具有显著的抑制活性, 抑菌率分别为 100%, 100%和 100%, 96%. 化合物 5aa 对链铬孢菌真菌的抑制率为 100%.

Cited by 6 publications

References 6 publications

Synthesis And Antibacterial Activity of 6-Bromo-2-(O-Aminophenyl)-3-Amino-Quinazolin-4(3h)-One From 6-Bromo,2-(O-Aminophenyl)-3,1-Benzoxazin-4(3h)-One

Synthesis And Antibacterial Activity of 6-Bromo-2-(O-Aminophenyl)-3-Amino-Quinazolin-4(3h)-One From 6-Bromo,2-(O-Aminophenyl)-3,1-Benzoxazin-4(3h)-One

Efficient Synthesis of Quinazolinones by Transition‐Metal‐Free Direct Aerobic Oxidative Cascade Annulation of Alcohols witho‐Aminoarylnitriles

Design, Synthesis, Characterization, and Antimicrobial Properties of New Azo Disperse Dyes Incorporating Quinazolinone-Pyrazolone Moieties and Their Applications for Dyeing of Polyester Fabrics

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Effects of the Substituent at C-2 Phenyl on the N-/O-Alkylation of Quinazolin-4(3H)-one and Anti-Tumor, Antimicrobial Activities of Some Compounds

Abstract: (50 µg/mL)对大肠杆菌和痢疾杆菌具有显著的抑制活性, 抑菌率分别为 100%, 100%和 100%, 96%. 化合物 5aa 对链铬 孢菌真菌的抑制率为 100%.

Cited by 6 publications

References 6 publications

Synthesis And Antibacterial Activity of 6-Bromo-2-(O-Aminophenyl)-3-Amino-Quinazolin-4(3h)-One From 6-Bromo,2-(O-Aminophenyl)-3,1-Benzoxazin-4(3h)-One

Synthesis And Antibacterial Activity of 6-Bromo-2-(O-Aminophenyl)-3-Amino-Quinazolin-4(3h)-One From 6-Bromo,2-(O-Aminophenyl)-3,1-Benzoxazin-4(3h)-One

Efficient Synthesis of Quinazolinones by Transition‐Metal‐Free Direct Aerobic Oxidative Cascade Annulation of Alcohols witho‐Aminoarylnitriles

Design, Synthesis, Characterization, and Antimicrobial Properties of New Azo Disperse Dyes Incorporating Quinazolinone-Pyrazolone Moieties and Their Applications for Dyeing of Polyester Fabrics

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Abstract: (50 µg/mL)对大肠杆菌和痢疾杆菌具有显著的抑制活性, 抑菌率分别为 100%, 100%和 100%, 96%. 化合物 5aa 对链铬孢菌真菌的抑制率为 100%.