Synthesis, Molecular Modelling and Biological Evaluation of 4‐Amino‐2(1H)‐quinazolinone and 2,4(1H,3H)‐Quinazolidone Derivatives as Antitumor Agents

Richter, Stephanie; Gioffreda, Barbara

doi:10.1002/ardp.201000312

Cited by 12 publications

(8 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 (3-Nitrophenyl)(4-(prop-2-ynyloxy)phenyl)methanone (19). 21 The m-nitrobenzoyl chloride (1.0 g, 5.38 mmol) was gradually added to a mixture of phenyl propargyl ether (18) (0.71 g, 5.38 mmol) and anhydrous aluminum chloride (1.07 g, 8.08 mmol) in dichloromethane at −10°C with continuous stirring. After addition, the mixture was stirred overnight at room temperature and quenched with 10% hydrochloric acid.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis and Structure–Activity Relationship Study of Chemical Probes as Hypoxia Induced Factor-1α/Malate Dehydrogenase 2 Inhibitors

et al. 2014

View full text Add to dashboard Cite

A structure-activity relationship study of hypoxia inducible factor-1α inhibitor 3-aminobenzoic acid-based chemical probes, which were previously identified to bind to mitochondrial malate dehydrogenase 2, was performed to provide a better understanding of the pharmacological effects of LW6 and its relation to hypoxia inducible factor-1α (HIF-1α) and malate dehydrogenase 2 (MDH2). A variety of multifunctional probes including the benzophenone or the trifluoromethyl diazirine for photoaffinity labeling and click reaction were prepared and evaluated for their biological activity using a cell-based HRE-luciferase assay as well as a MDH2 assay in human colorectal cancer HCT116 cells. Among them, the diazirine probe 4a showed strong inhibitory activity against both HIF-1α and MDH2. Significantly, the inhibitory effect of the probes on HIF-1α activity was consistent with that of the MDH2 enzyme assay, which was further confirmed by the effect on in vitro binding activity to recombinant human MDH2, oxygen consumption, ATP production, and AMP activated protein kinase (AMPK) activation. Competitive binding modes of LW6 and probe 4a to MDH2 were also demonstrated.

show abstract

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis and Structure–Activity Relationship Study of Chemical Probes as Hypoxia Induced Factor-1α/Malate Dehydrogenase 2 Inhibitors

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Several reports have revealed that the unique quinazoline scaffolds possess several and diverse pharmacological activities such as antimicrobial, antimalarial, anticonvulsant, anti-inflammatory, antihypertensive, cholinesterase inhibitory, anti-diabetic, and anticancer activities [1]. Among the most important quinazoline families are quinazoline-2,4(1H,3H)-dione derivatives, and the various studies have reported several analogues representing a wide variety of biological activities, for example, antimicrobial [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18], anticancer [19][20][21][22][23][24][25][26][27][28][29][30][31][32], antiplatelet [33], antihypertensive [34], antioxidant [35], anticonvulsant [36][37][38], anti-inflammatory [39], phosphodiesterase (PDE) 4 inhibition [40], 5-HT3A receptor antagonist [41], and cyclin-dependent kinase 5 (CDK5) inhibition [42].…”

Section: Introductionmentioning

confidence: 99%

Discovery of Quinazoline-2,4(1H,3H)-Dione Derivatives as Potential Antibacterial Agent: Design, Synthesis, and Their Antibacterial Activity

et al. 2022

View full text Add to dashboard Cite

In this paper, we report on the design and synthesis of a novel series of quinazoline-2,4(1H,3H)-dione derivatives as fluoroquinolone-like inhibitors of bacterial gyrase and DNA topoisomerase IV to identify and develop antimicrobial agents to prevent bacterial resistance problems. Their structures were confirmed using spectroscopic analyses (IR, NMR, and EI-MS). The novel quinazoline-2,4(1H,3H)-dione derivatives were evaluated for their antimicrobial activities against Gram-positive and Gram-negative bacterial strains using the Agar well diffusion method to study the antimicrobial activities and compared them with the standard drugs. Most compounds displayed moderate activity. Among the tested compounds, the most promising compounds 13 and 15 provided broad bioactive spectrum against Gram-positive and Gram-negative strains compared to the standard drugs.

show abstract

“…Nitrogen-containing heterocyclic compounds such as C4-substituted quinazolinone and quinazolinediones exhibit a wide range of biological properties such as Na + /Ca 2+ exchange inhibitor, anti-inflammatory, anticancer, antimalarial, antidiabetic, and antihypertensive activities (Figure ). Hence, it has a central role in drug development, medicinal chemistry, and corresponding drug-target relationships superintended for specific biological activity and drug action.…”

Section: Introductionmentioning

confidence: 99%

Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives

2021

View full text Add to dashboard Cite

For the first time, the sequential reaction of peroxyoxindole that involves base-promoted oxidative fragmentation to isocyanate formation and primary amine or amino alcohol accelerated skeletal rearrangement to synthesize exo-olefinic-substituted quinazolinone or oxazoloquinazolinone is reported. The advantages of this new reaction include a broad substrate scope and transition-metal-free and room-temperature conditions. The formation of the isocyanate as a key intermediate that accelerates oxidative skeletal rearrangement has been confirmed by trapping experiments and spectroscopic evidence.

show abstract

Synthesis, Molecular Modelling and Biological Evaluation of 4‐Amino‐2(1H)‐quinazolinone and 2,4(1H,3H)‐Quinazolidone Derivatives as Antitumor Agents

Abstract: A series of 6-benzoyl-, 6-arylthio- and 6-arylsulfonyl-4-amino-2(1H)-quinazolinones and -2,4(1H,3H)-quinazolinediones were prepared. They were evaluated in vitro for their cytotoxicity against the NCI-60 cancer cell lines.

Cited by 12 publications

References 24 publications

Synthesis and Structure–Activity Relationship Study of Chemical Probes as Hypoxia Induced Factor-1α/Malate Dehydrogenase 2 Inhibitors

Synthesis and Structure–Activity Relationship Study of Chemical Probes as Hypoxia Induced Factor-1α/Malate Dehydrogenase 2 Inhibitors

Discovery of Quinazoline-2,4(1H,3H)-Dione Derivatives as Potential Antibacterial Agent: Design, Synthesis, and Their Antibacterial Activity

Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives

Contact Info

Product

Resources

About