Synthesis and reactions of 3-aminotetrachloroquinazolin-2,4-dione

Hassan, M. A.; Younes, Ahmed Mohamed Mosalem; Taha, Mohamed; Abdel-Monsef, Abou-Bakr Haredy

doi:10.5155/eurjchem.2.4.514-518.479

Cited by 14 publications

(12 citation statements)

References 11 publications

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“…In the present study, 3-(4-acetyl-phenyl)-1H-quinazolin-2,4-dione 1 was utilized as a starting compound for the synthesis of the quinazolindione skeletons (2)(3)(4)(5)(6)(7)(8)(9). The computational methodologies like homology modeling, active site prediction, and virtual screening approach have been developed for hit identification against cancer.…”

Section: Resultsmentioning

confidence: 99%

“…The quinazolindione scaffold and its derivatives have gained a wide spectrum in the medicinal and pharmaceutical chemistry fields, due to their promising biological activities like antifungal, antibacterial, and anticancer …”

Section: Introductionmentioning

confidence: 99%

“…[6] Mutation in Rho7 protein was identified as possible pathogenic in patients with breast cancer cell lines (MCF-7) and hepatocellular cancer cell lines (HepG2). [5] The quinazolindione scaffold and its derivatives have gained a wide spectrum in the medicinal and pharmaceutical chemistry fields, [7][8][9] due to their promising biological activities like antifungal, antibacterial, and anticancer. [10][11][12] In view of the facts mentioned above and as a part of our efforts to synthesis of new anticancer drug candidates, [13,14] herein, several derivatives of quinazolindione analogues were synthesized and screened for their antiproliferative activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, in vitro biological evaluation and in silico docking studies of new quinazolin‐2,4‐dione analogues as possible anticarcinoma agents

Abdelmonsef

Mosallam

2020

Journal of Heterocyclic Chem

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Today, cancer is considered as one of the major reasons of death in human beings worldwide. We reported herein the synthesis, anticancer activity, and in silico docking studies of a series of nine quinazolindione‐based scaffolds bearing pyrimidine, pyridine, pyran, and pyrazole moieties (1‐9) through Michael addition, Vilsmeier‐Haack, Claisen‐Schmidt, and nucleophilic addition reactions. The chemical structures of the newly prepared compounds were ascertained by means of their spectral analysis techniques like IR, 1H‐nuclear magnetic resonance (NMR), 13C‐NMR, mass spectroscopy, and elemental analysis. This work was conducted to investigate the implication of Rho7 protein in breast and hepatocellular cancer cells aggressively. MCF‐7 and HepG2 cells have been selected as models for the effect of protein expression on breast and hepatocellular cancers cell growth. All prepared compounds were biologically evaluated for their antiproliferative efficacy on hepatic cancer cell lines (HepG2) and breast cancer cell lines (MCF‐7); also, their effects on normal cell lines (BALB/3T3) were studied. Moreover, in silico molecular docking studies were studied for the compounds against the binding site of Homo sapiens Rho7 protein. The pharmacokinetic properties of the newer compounds were also evaluated using various computational tools. The compounds showed interesting interactions with satisfactory docking scores to the target Rho7; thus, they may act as promising potent drug candidates against cancer.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, in vitro biological evaluation and in silico docking studies of new quinazolin‐2,4‐dione analogues as possible anticarcinoma agents

Abdelmonsef

Mosallam

2020

Journal of Heterocyclic Chem

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“…In this study, our target was to synthesize novel quinazolindiones derivatives which based on the reaction between glycine ethyl ester hydrochloride and Nphenylsulphonyloxyphtahlimide via Lossen rearrangement [8][9] giving quinazoline-2,4-dione derivatives. In the course of the present work, we found, reacting of N-phenylsulphonyl oxyphthalimide (1) with glycine ethyl ester hydrochloride in pyridine under reflux for 9 hours afford (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid ethyl ester (2), which then converted to starting material (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid hydrazide (3) in a good yield through its reaction with hydrazine hydrate in absolute ethanol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and spectral characterization of some heterocyclic nitrogen compounds

et al. 2013

Self Cite

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KEYWORDSQuinazolines and pyrimidines are most important class of compounds and have received much attention from both synthetic and medicinal chemists, because of the diverse range of their pharmacological properties. Owing to their versatile chemotherapeutic importance, a number of quinazolin-2,4-dione derivatives were synthesized using appropriate synthetic routes and characterized by IR, 1 H NMR, MS, and elemental analysis.Arylidine Hydrazide Pyrimidines Carbon disulphide Quinazolin-2,4-dione Glycine ethyl ester hydrochloride

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“…Various literatures report numerous 2,4(1H,3H)quinazolinedione analogues showing a wide variety of biological activities such as anticancer [7][8][9][10][11][12][13][14][15][16][17][18][19][20], antimicrobial [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37], antihypertensive [38][39][40], anticonvulsant [41][42][43][44][45][46][47][48][49], anti-inflammatory [50], 5-hydroxytryptamine 3 (5-HT 3 ) receptor antagonist [51], phosphodiesterase (PDE) 4 inhibition [52,53], calcium-independent phosphodiesterase enzyme inhibition (CaIPDE) [54], cyclin-dependent kinase 5 (CDK5) inhibition…”

Section: Introductionmentioning

confidence: 99%

A Series of 2,4(1H,3H)-Quinazolinedione Derivatives: Synthesis and Biological Evaluation as Potential Anticancer Agents

Akgün¹,

Yilmaz²,

Cetin-Atalay³

et al. 2015

LDDD

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A series of 6,7-disubstituted-3-{2-[4-(substituted)piperazin-1-yl]-2-oxoethyl}quinazoline-2,4(1H,3H)-dione derivatives (7-34) were synthesized and their structures were elucidated on the basis of analytical and spectral (UV, IR, 1 H-NMR, 13 C-NMR and MS) data. These synthesized compounds were evaluated for their in vitro cytotoxicities against a panel of three human cancer cell lines. According to the cytotoxicity screening results, 3-{2-[4-(4-chlorobenzyl)piperazin-1-yl]-2-oxoethyl} quinazoline-2,4(1H,3H)-dione (7) presented the highest activity against HUH-7, MCF-7 and HCT-116 cell line with the IC 50 values of 2.5, 6.8 and 4.9 µM, respectively.

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Synthesis and reactions of 3-aminotetrachloroquinazolin-2,4-dione

Cited by 14 publications

References 11 publications

Synthesis, in vitro biological evaluation and in silico docking studies of new quinazolin‐2,4‐dione analogues as possible anticarcinoma agents

Synthesis, in vitro biological evaluation and in silico docking studies of new quinazolin‐2,4‐dione analogues as possible anticarcinoma agents

Synthesis and spectral characterization of some heterocyclic nitrogen compounds

A Series of 2,4(1H,3H)-Quinazolinedione Derivatives: Synthesis and Biological Evaluation as Potential Anticancer Agents

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