Cytotoxicity and anti-HIV evaluations of some new synthesized quinazoline and thioxopyrimidine derivatives using 4-(thiophen-2-yl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione as synthon

Mohamed, Y. A.; Amr, Abd El‐Galil E.; Mohamed, S.A.; Abdalla, Mohamed M.; Al-Omar, Mohamed A.; Shfik, Samira H.

doi:10.1007/s12039-012-0242-4

Cited by 33 publications

(11 citation statements)

References 21 publications

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“…These compounds are also used for treatment of high blood pressure, prevention of folic acid synthesis through inhibition of the enzyme dihydrofolate reductase and inhibition of activity of EGFR over-expressed in the several forms of cancer. Interaction with cytoskeleton, DNA topoisomerase and induction of apoptosis are other effects of the spiroquinazolinone compounds (Cubedo et al, 2006;Mohamed et al, 2012;Krishnan et al, 2011;Ovádeková et al, 2005;Selvam et al, 2011). The spiroquinazolinone compounds can be proposed as effective agents for more investigation in the drug developments.…”

Section: Introductionmentioning

confidence: 99%

Spiroquinazolinone-induced cytotoxicity and apoptosis in K562 human leukemia cells: alteration in expression levels of Bcl-2 and Bax

et al. 2015

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-Spiroquinazolinone compounds have been considered as a new series of potent apoptosis-inducing agents. In this study, anti-proliferative and apoptotic effects of the derivatives from the spiroquinazolinone family were investigated in the human chronic myeloid leukemia K562 cells. The K562 cells were treated with various concentrations of the spiroquinazolinone (10-300 μM) for 3 days and cell viability was determined by MTT growth inhibition assay. 4t-QTC was more active among these compounds with IC50 of 50 ± 3.6 μM and was selected for further studies. Apoptosis, as the mechanism of cell death was investigated morphologically by acridine orange/ethidium bromide (AO/EtBr) double staining, cell surface expression assay of phosphatidyl serine by Annexin V/PI technique, as well as the formation of DNA ladder. The K562 cells underwent apoptosis upon a single dose (at IC50 value) of the 4t-QTC compound, and over-expressed caspase-3 expression by more than 1.7-fold, following a 72 hr treatment. Furthermore, RT-PCR and Western blot analysis revealed that treatment of the K562 cells with 4t-QTC down-regulates and up-regulates the expression of Bcl-2 (anti-apoptotic) and Bax (pro-apoptotic), respectively. Based on the present data, it seems that these compounds from the spiroquinazolinone family are good candidates for further evaluation as an effective chemotherapeutic family acting through induction of apoptosis in chronic myeloid leukemia.

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Section: Introductionmentioning

confidence: 99%

Spiroquinazolinone-induced cytotoxicity and apoptosis in K562 human leukemia cells: alteration in expression levels of Bcl-2 and Bax

et al. 2015

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“…The pyrazolopyrimidines 11a–b were obtained by cyclization of pyrazolones 10a–b with thiourea in refluxing ethanol containing 10% potassium hydroxide (Scheme 2). The formation of pyrazolopyrimidinethione 11 is believed to be formed via initial condensation of thiourea with the carbonyl group of 10 and subsequent elimination of water followed by addition NH 2 of thiourea on the double bond system of 10 [21, 28–31]. Pyrazolopyrimidinethiones 11a–b was used as building blocks for the synthesis of condensed heterocycles.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and in vitro antimicrobial activity of novel fused pyrazolo[3,4-c]pyridazine, pyrazolo[3,4-d]pyrimidine, thieno[3,2-c]pyrazole and pyrazolo[3′,4′:4,5]thieno[2,3-d]pyrimidine derivatives

Reheim

Baker

2017

Chemistry Central Journal

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BackgroundSome novel substituted pyrazolone, pyrazolo[3,4-c]pyridazine, pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidinone, thieno[3,2-c]pyrazole and pyrazolo[3′,4′:4,5]thieno[2,3-d]pyrimidine derivatives have been reported to possess various pharmacological activities like antimicrobial, antitumor and anti-inflammatory.ResultsA novel series of azoles and azines were designed and prepared via reaction of 1,3-diphenyl-1H-pyrazol-5(4H)-one with some electrophilic and nucleophilic reagents. The structures of target compounds were confirmed by elemental analyses and spectral data.ConclusionsThe antimicrobial activity of the target synthesized compounds were tested against various microorganisms such as Escherichia coli; Bacillus megaterium; Bacillus subtilis (Bacterial species), Fusarium proliferatum; Trichoderma harzianum; Aspergillus niger (fungal species) by the disc diffusion method. In general, the novel synthesized compounds showed a good antimicrobial activity against the previously mentioned microorganisms.

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“…Quinazolinones are pharmacophoric scaffold ubiquitous in various biologically active natural products, synthetic compounds, pharmaceutical drugs, agrochemicals and veterinary products [1]. The chemical structure of quinazolinones constitute a crucial scaffold of compounds with various therapeutic and biological activities such as antimalarial [2], antimicrobial [3,4], antitubercular [5], anticonvulsant [6], anticancer [7], antihypertensive [8], anti-diabetic [9], anti-inflammatory [10], anti-cholinesterase [11], cellular phosphorylation inhibition [12], dihydrofolate reductase inhibition [13], kinase inhibitory activities [14], inhibitors of tubuline polymerization [15], diuretic [16], antipsychotic [17], dopamine agonists [18] and anti-HIV [19]. Quinazolinones (Figure 1) is a core scaffold for the structure of more than 200 naturally occurring alkaloids isolated from different plant families and from various microorganisms such as Bacillus cereus, Peganum nigellastrum, Dichroa febrifuga and Bouchardatia neurococca [20].…”

Section: Introductionmentioning

confidence: 99%

Biological Activity of Quinazolinones

Radwan¹,

Alanazi²

2020

Quinazolinone and Quinazoline Derivatives

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The chemical structure of quinazolinones includes benzene ring fused with 2-pyrimidinone (1), 4-pyrimidinone (2) or 2,4-pyrimidinedione (3) ring, and are named as quinazolin-2(1H)-one, quinazolin-4(3H)-one or quinazolin-2,4(1H, 3H)-one, respectively. The chemical structure of quinazolinones constitutes a crucial scaffold of natural and synthetic compounds with various therapeutic and biological activities. Quinazolinones are first synthesized by Stefan Niementowski (1866-1925) and named after Niementowski quinazolinone synthesis. Quinazolinones have strongly attracted the interest of medicinal chemist as they constitute a large class of compounds that exhibited broad spectrum of biological activities including antimicrobial, antimalarial, anticonvulsant, anticancer, antileishmanial, anti-inflammatory, etc. This chapter provides a brief overview on the recent advances on chemical and pharmacological aspects of quinazolinone derivatives published in the last decade.

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Cytotoxicity and anti-HIV evaluations of some new synthesized quinazoline and thioxopyrimidine derivatives using 4-(thiophen-2-yl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione as synthon

Abstract: A series of dihydrobenzo[h]quinazoline derivatives is synthesized starting from compounds (I), (IX) or (XVII).

Cited by 33 publications

References 21 publications

Spiroquinazolinone-induced cytotoxicity and apoptosis in K562 human leukemia cells: alteration in expression levels of Bcl-2 and Bax

Spiroquinazolinone-induced cytotoxicity and apoptosis in K562 human leukemia cells: alteration in expression levels of Bcl-2 and Bax

Synthesis, characterization and in vitro antimicrobial activity of novel fused pyrazolo[3,4-c]pyridazine, pyrazolo[3,4-d]pyrimidine, thieno[3,2-c]pyrazole and pyrazolo[3′,4′:4,5]thieno[2,3-d]pyrimidine derivatives

Biological Activity of Quinazolinones

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