Utility of (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid hydrazide in the synthesis of some heterocyclic nitrogen compounds

Hassan, M. A.; Seleem, Mohamed N.; Younes, Ahmed Mohamed Mosallem; Taha, Mohamed; Abdelmonsef, Aboubakr H.

doi:10.5155/eurjchem.4.2.168-171.762

Cited by 7 publications

(2 citation statements)

References 14 publications

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“…The synthetic strategy pathway for synthesis of hydrazide 1 is reported earlier in previous works. [18][19][20][21] Then, compound 1 was used as starting material for synthesis of new compounds 2 to 8 as declared in Scheme 1. Furthermore, the new heterocyclic moiety pyrazole in compound 2 was prepared via Knorr pyrazole synthesis by treatment of compound 1 with β-di-ketone such as acetylacetone in 79% yield as reported in Scheme 2.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization, Antibacterial Activity, and Computer-Aided Design of Novel Quinazolin-2,4-dione Derivatives as Potential Inhibitors Against Vibrio cholerae

El‐Naggar

Mohamed

Mosallam

et al. 2020

Evol Bioinform Online

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Cholera is a bacterial disease featured by dehydration and severe diarrhea. It is mainly caused by alimentary infection with Vibrio cholerae. Due to the wide applicability of quinazolin-2,4-dione compounds in medicinal and pharmaceutical chemistry, a new series of N-containing heterocyclic compounds was synthesized. We used the in silico docking method to test the efficacy of quinazolin-2,4-dione compounds in the prevention of cholera in humans. The newly synthesized compounds showed strong interactions and good binding affinity to outer membrane protein OmpU. Moreover, the pharmacokinetic properties of the newly synthesized compounds, such as absorption, distribution, metabolic, excretion, and toxicity (ADMET), were predicted through in silico methods. Compounds with acceptable pharmacokinetic properties were tested as novel ligand molecules. The synthesized compounds were evaluated in vitro for their antibacterial activity properties against Gram-negative Escherichia coli O78 strain using the minimum inhibition concentration (MIC) method. Compounds 2 and 6 showed reproducible, effective antibacterial activity. Hence, our study concludes that the quinazolin-2,4-dione derivatives 1 to 8 may be used as promising drug candidates with potential value for the treatment of cholera disease.

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Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization, Antibacterial Activity, and Computer-Aided Design of Novel Quinazolin-2,4-dione Derivatives as Potential Inhibitors Against Vibrio cholerae

El‐Naggar

Mohamed

Mosallam

et al. 2020

Evol Bioinform Online

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“…Various natural as well as synthetic compounds containing the quinazolin‐2,4‐dione core moiety represent an important class of heterocyclic compounds, possessing a broad spectrum of biological importance [10–14]. They have gained considerable attention due to their pharmacological and medicinal applications [11,15–17].…”

Section: Introductionmentioning

confidence: 99%

A search for antiinflammatory therapies: Synthesis, in silico investigation of the mode of action, and in vitro analyses of new quinazolin‐2,4‐dione derivatives targeting phosphodiesterase‐4 enzyme

Abdelmonsef

Abd-Elhakeem

Mosallam

et al. 2021

Journal of Heterocyclic Chem

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Inflammation is the response of the body's immune system to harmful stimuli. The expression of phosphodiesterase 4 enzyme (PDE4) was demonstrated in many inflammatory cells. Thus, it was considered an attractive therapeutic target for combating inflammatory disorders. In the present study, a novel class of quinazolin‐2,4‐dione analogues 1‐17a,b was synthesized. Structures of the newly synthesized compounds were characterized by means of spectral and elemental analysis. Additionally, molecular docking studies for the new synthetic compounds were performed using PyRx—virtual screening tool to demonstrate the possible binding pattern mode of interactions within the active site region of the PDE4 enzyme. The antiinflammatory activity of the synthesized compounds was also in vitro examined using inhibition of protein denaturation, anti‐proteinase effect, and membrane stabilization assay. The in silico docking studies revealed that the newly synthesized compounds were well accommodated by the active site region of the target protein through a network of noncovalent interactions such as hydrogen bonds and pi‐stacking, which contributed to the enhancement of affinity and stability between the compounds and the target protein. They exhibited better docking scores when compared with reference drugs diclofenac and coumarin. In addition, in vitro testing revealed that the compounds had moderate to good antiinflammatory effects. The biological study agreed with in silico approach, which revealed that the compounds had promising antiinflammatory activity. Hence, our detailed results can facilitate the rational drug design targeting PDE4 enzyme.

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Synthesis of Some Novel Quinazolinone Derivatives with Anticipated Biological Activity

Marzouk

Shaker

Farghaly

et al. 2017

Journal of Heterocyclic Chem

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The behavior of the benzoxazinone derivative 1 toward nitrogen and carbon nucleophiles was investigated and yielded compounds 2–4, 6, and 7. The oxadiazol derivatives 9–12 were obtained from the interaction of hydrazide 8 with benzoic acid in the presence of phosphoryl chloride and/or carbon disulfide in the presence of KOH followed by alkylation with ethyl iodide and hydrazinolysis with hydrazine hydrate, respectively. The quinazolinone derivatives 13 and 22 were utilized to construct new heterocyclic systems 15–21, 23, and 24 via interaction with different carbon electrophiles. Some of the newly synthesized compounds were characterized on the bases of spectroscopic data. Some of the synthesized compounds were screened for antimicrobial activity.

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Utility of (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid hydrazide in the synthesis of some heterocyclic nitrogen compounds

Cited by 7 publications

References 14 publications

Synthesis, Characterization, Antibacterial Activity, and Computer-Aided Design of Novel Quinazolin-2,4-dione Derivatives as Potential Inhibitors Against Vibrio cholerae

Synthesis, Characterization, Antibacterial Activity, and Computer-Aided Design of Novel Quinazolin-2,4-dione Derivatives as Potential Inhibitors Against Vibrio cholerae

A search for antiinflammatory therapies: Synthesis, in silico investigation of the mode of action, and in vitro analyses of new quinazolin‐2,4‐dione derivatives targeting phosphodiesterase‐4 enzyme

Synthesis of Some Novel Quinazolinone Derivatives with Anticipated Biological Activity

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