Synthesis and biological evaluation of some 3H-quinazolin-4-one derivatives

Sharaf, A. M.; Ragab, Sherif Shaban; El‐Barbary, A. A.; Shaban, Elkhabiry; Sayed, Ibrahim El Tantawy El

doi:10.1007/s13738-021-02315-8

Cited by 6 publications

(5 citation statements)

References 34 publications

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“…The simplicity and versatility of this process led to the production of a wide range of bioactive agents. Based on these findings and in combination with our interest in anticancer agents [28–31] along with our previous research on pyrimidine‐containing molecules, [32–34] we report, herein, a series of new hydrazone derivatives 4 a – l (Scheme 1) containing spirocyclic aminopyrimidine and aryl alkanesulfonate moieties. To access the starting compound, we used a Biginelli reaction which is an example of the multicomponent reaction [35] by which cyclohexanone, malononitrile and thiourea were reacted in one‐pot process to produce the spirocyclic pyrimidine.…”

Section: Introductionmentioning

confidence: 72%

Synthesis and Antiproliferative Properties of Some Spirocyclic Pyrimidine Hydrazones

Ragab,

Sweed,

Srour

2024

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A new series of hydrazone derivatives incorporating spirocyclic aminopyrimidine with aryl alkanesulfonates were synthesized. The targeted products were obtained in excellent yields via an acid catalyzed reaction of spirocyclic hydrazinopyrimidine with aryl aldehyde sulfonates. The structures of the synthesized hydrazones were studied by the different spectroscopic tools, in addition to the high resolution mass analysis. The antiproliferative activities of the compounds were tested in vitro against the National Cancer Institute (NCI) 60 cell panel by the Developmental Therapeutics Program. Amongst the tested hydrazone compounds, the methansulfonate derivatives showed the highest activities against lung, brain, kidney, and breast cancers.

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Section: Introductionmentioning

confidence: 72%

Synthesis and Antiproliferative Properties of Some Spirocyclic Pyrimidine Hydrazones

Ragab,

Sweed,

Srour

2024

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“…Therefore, α-APs were deemed a worthy choice for AgNPs dispersion to bring extra synergistic antibacterial properties as part of a sustainable approach. Remarkably, our group has long been involved in developing different series of phosphonate derivatives in medical applications as antibacterial agents [ 45 , 46 ], urokinase-type plasminogen inhibitors [ 47 ], DNA gyrase inhibitors [ 48 ], anticancer [ 49 ], antifungal agents [ 49 ]. This is in addition to designing and synthesizing other potent antibacterial agents for various industrial applications [ 22 , 50 , 51 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Docking Study of Novel Thioureidophosphonate-Incorporated Silver Nanocomposites as Potent Antibacterial Agents

et al. 2023

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Newly synthesized mono- and bis-thioureidophosphonate (MTP and BTP) analogues in eco-friendly conditions were employed as reducing/capping cores for 100, 500, and 1000 mg L−1 of silver nitrate. The physicochemical properties of silver nanocomposites (MTP(BTP)/Ag NCs) were fully elucidated using spectroscopic and microscopic tools. The antibacterial activity of the nanocomposites was screened against six multidrug-resistant pathogenic strains, comparable to ampicillin and ciprofloxacin commercial drugs. The antibacterial performance of BTP was more substantial than MTP, notably with the best minimum inhibitory concentration (MIC) of 0.0781 mg/mL towards Bacillus subtilis, Salmonella typhi, and Pseudomonas aeruginosa. Among all, BTP provided the clearest zone of inhibition (ZOI) of 35 ± 1.00 mm against Salmonella typhi. After the dispersion of silver nanoparticles (AgNPs), MTP/Ag NCs offered dose-dependently distinct advantages over the same nanoparticle with BTP; a more noteworthy decline by 4098 × MIC to 0.1525 × 10−3 mg/mL was recorded for MTP/Ag-1000 against Pseudomonas aeruginosa over BTP/Ag-1000. Towards methicillin-resistant Staphylococcus aureus (MRSA), the as-prepared MTP(BTP)/Ag-1000 displayed superior bactericidal ability in 8 h. Because of the anionic surface of MTP(BTP)/Ag-1000, they could effectively resist MRSA (ATCC-43300) attachment, achieving higher antifouling rates of 42.2 and 34.4% at most optimum dose (5 mg/mL), respectively. The tunable surface work function between MTP and AgNPs promoted the antibiofilm activity of MTP/Ag-1000 by 1.7 fold over BTP/Ag-1000. Lastly, the molecular docking studies affirmed the eminent binding affinity of BTP over MTP—besides the improved binding energy of MTP/Ag NC by 37.8%—towards B. subtilis-2FQT protein. Overall, this study indicates the immense potential of TP/Ag NCs as promising nanoscale antibacterial candidates.

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“…There are no licensed antivirals to target viruses of the Coronaviridae family. Based on our experience in the synthesis of bioactive compounds, [4–7] we intended to develop new chemical designs that could be investigated as antiviral agents. Our last studies demonstrated the good bioactivity of spirocyclic thiopyrimidine derivatives as antibacterial agents [8] and this encouraged us to explore different series of these compounds to study their antiviral activity.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antiviral Evaluation, and Molecular Dynamics Simulation Studies of New Spirocyclic Thiopyrimidinones as Anti HCoV‐229E

Ragab

Sweed

Elrashidy

et al. 2022

Chemistry & Biodiversity

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The current pandemic threat presented by viral pathogens like SARS-CoV-2 (COVID-19) suggests that virus emergence and dissemination are not geographically confined. As a result, the quest for antiviral agents has become critical to control this pandemic. In the current study, we provide a novel family of spirocyclic thiopyrimidinone derivatives whose cytotoxicity and antiviral efficacy were investigated against human coronavirus 229E (HCoV-229E) as a model for the Coronaviridae family. We utilized MTT and cytopathic effect (CPE) inhibitory tests on green monkey kidney (vero-E6) cell lines. The new molecules showed varied degrees of antiviral activity against the vero-E6 cell lines with minimal cytotoxicity. With a high level of a selective index (SI = 14.8), compound 9 showed outstanding inhibitory ability and could effectively suppress the human coronavirus 229E. Molecular dynamics simulation (MD) studies were performed to measure the interaction and stability of the protein-ligand complex in motion. The MD results for the most active compound 9 explored remarkable interactions with the binding pockets of the main protease (Mpro) of SARS-CoV-2 enzyme confirming the results gained from in vitro experiments. ADMET properties were also predicted for all the tested compounds. All these results demonstrated that the novel spirocyclic thiopyrimidinone derivatives would have the potential to be safe, low-cost chemical compounds that might be used as a novel therapeutic option for Coronaviridae viruses like COVID-19.

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Synthesis and biological evaluation of some 3H-quinazolin-4-one derivatives

Cited by 6 publications

References 34 publications

Synthesis and Antiproliferative Properties of Some Spirocyclic Pyrimidine Hydrazones

Synthesis and Antiproliferative Properties of Some Spirocyclic Pyrimidine Hydrazones

Synthesis, Characterization, and Docking Study of Novel Thioureidophosphonate-Incorporated Silver Nanocomposites as Potent Antibacterial Agents

Design, Synthesis, Antiviral Evaluation, and Molecular Dynamics Simulation Studies of New Spirocyclic Thiopyrimidinones as Anti HCoV‐229E

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