Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors

Bertelli, L.

doi:10.1016/s0223-5234(00)90154-5

Cited by 41 publications

(7 citation statements)

References 6 publications

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“…Compounds containing scaffold A are reported in the recent literature as negative allosteric modulators of metabotropic glutamate receptors 2 and 3 (dual mGlu2/mGlu3 NAMs) 4 and as non-camptothecin Topoisomerase 1 (Top1) inhibitors 5 , while they have never been studied earlier as GABA A receptor ligands. Only tricyclic systems, containing pyrazole, triazole, and imidazole rings, which are condensed differently with quinoxaline, quinazoline and ftalazine, are reported for this study [6][7][8][9] .…”

Section: Introductionmentioning

confidence: 99%

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABA_A receptor subtype and molecular dynamic study

Guerrini

Ciciani

Ciattini

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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To investigate the binding affinity of GABAA receptor subtype, new pyrazolo [1,5-a]quinazolines were designed, synthesized, and in vitro evaluated. These compounds, 5-deaza analogues of pyrazolo[5,1-c][1,2,4]benzotriazine derivatives which were already studied in our research group, permit us to evaluate the relevance of the nitrogen or the oxygen atom at 5-position of the tricyclic scaffold. Molecular dynamic study was done on a set of the new and known ligands to rationalize and to explain the lack of affinity on the 4- or 5-substituted new derivative. In fact, from biological results, it can be found that the only 5-unsubstituted new derivative, compound 15, has receptor recognition (Ki = 834.7 nM).

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Section: Introductionmentioning

confidence: 99%

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABA_A receptor subtype and molecular dynamic study

Guerrini

Ciciani

Ciattini

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…(12), Table 2) which was the first promising A 2A AR antagonist with non xanthine structure [141][142][143]. The triazoloquinazoline compounds generally present higher affinity for A 2A AR versus A 1 AR [141][142][143][144].…”

Section: A 2a Ar Antagonists: Development and Structure-activity-relamentioning

confidence: 99%

A2A Receptor Ligands: Past, Present and Future Trends

Manera

Saccomanni²

2010

CTMC

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The adenosine A(2A) receptor is a member of the G protein-coupled receptor family and mediates multiple physiological effects of adenosine, both at the central nervous system and at peripheral tissues. Increasing evidence relates the A(2A) receptor with several pathological conditions such as neurodegenerative disorders, inflammation, pharmacological stress, and wound healing renewing the interest in A(2A) receptor agonists and antagonists as promising leads for drugs. However some of them initially tested in clinical trials presented several side effects, short half-life, lower solubility, and in some cases a lack of effects, perhaps attributable to receptor desensitization or to low receptor density in the targeted tissue. For these reasons it is evident that additional rational chemical modifications of the existing A(2A) receptor ligands to improve their affinity/selectivity and bioavailability as well as further studies to get new template for A(2A)AR ligands are necessary. The purpose of this review is to analyze and summarize the past and the present aspects related to the medicinal chemistry of A(2A) receptor ligands. Moreover their current and possible therapeutic applications have been also highlighted.

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“…Quinazolines also display biological roles like cellular phosphorylation inhibitors, ligands for benzodiazepine and GABA receptors in the central ner-vous system (Bertelli et al, 2000) and as DNA binding motifs (Lewerenz et al, 2003;Malecki et al, 2004). They have also shown to possess effectual α-adrenergic blocking activity.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anticancer activity of novel Triazole substituted Quinazoline Hybrids

Karunakar

Gujjewar²,

Sharma³

et al. 2020

ijrps

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Quinazolines and 1,2,4-triazoles are important class of nitrogen containing heterocyclic compounds having immense biological importance. From the literature review, pharmacokinetic properties of a drug can be modified or enhanced by building a triazole moiety into a compound like quinazoline. Therefore, the study of new hybrid systems which combines triazole system with quinazoline is still seemed warranted. In the present study, a sequence of novel 1,2,4-triazole derivatives containing quinazolinyl moiety were designed, synthesized and screened for their in vitro anticancer activity. Thirteen new hybrids are synthesized from readily accessible 5-bromoanthranilic acid. All the hybrid compounds were well explicated by IR, 1H, 13C NMR, and mass spectral data. Out of 13, some of the compounds manifested moderate to good antiproliferative activity against two cancer cell lines (HepG2 and MCF7). Remarkably, compounds 8A, 16H and 16K displayed potent activity (14- 49 µM) on both HepG2 (liver carcinoma) and MCF-7 (breast cancer) cell lines whereas compounds 8B, 8F, 16L, and 15 displayed substantial activity against HepG2 cancer cell line (34-65 µM). Synthetic approach described here is very simple and can be used for the syntheses of related compounds library which is useful for the exploration of further biological activities and is currently underway in our laboratory

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Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors

Cited by 41 publications

References 6 publications

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABA_A receptor subtype and molecular dynamic study

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABA_A receptor subtype and molecular dynamic study

A2A Receptor Ligands: Past, Present and Future Trends

Design, Synthesis and Anticancer activity of novel Triazole substituted Quinazoline Hybrids

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Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors

Cited by 41 publications

References 6 publications

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABAA receptor subtype and molecular dynamic study

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABAA receptor subtype and molecular dynamic study

A2A Receptor Ligands: Past, Present and Future Trends

Design, Synthesis and Anticancer activity of novel Triazole substituted Quinazoline Hybrids

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Product

Resources

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Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABA_A receptor subtype and molecular dynamic study

Pyrazolo[1,5-a]quinazoline scaffold as 5-deaza analogue of pyrazolo[5,1-c][1,2,4]benzotriazine system: synthesis of new derivatives, biological activity on GABA_A receptor subtype and molecular dynamic study