Synthesis and characterization of quinazolinone derivatives against mammary carcinoma

Jose, Asha; Chittethu, Amrutha B; Sankaran, Sathianarayanan; Suja, Saranya Tulasidharan; Ekambaram, Kumar Prem

doi:10.1016/j.jopr.2013.07.033

Cited by 2 publications

(4 citation statements)

References 9 publications

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“…The absorbance was measured using a microplate reader at a wavelength of 540 nm. 21 The vehicle control was designated as the well containing live cells with the culture medium. 22 The percentage growth inhibition was calculated using the formula depicted below and concentration of test drug needed to inhibit cell growth by 50% i.e., the half maximal cytotoxic inhibitory concentration (CTC 50 values) generated from the dose-response curves for each cell line.…”

Section: Assessment Of Cytotoxicity By Mtt Assaymentioning

confidence: 99%

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Sathianarayanan¹,

Chittethu²,

Jose³

et al. 2017

JYP

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Objective: The present study was aimed to determine cytotoxic and apoptotic activity of isatin semicarbazones against mammary carcinoma. Methodology: The preparation of these target compounds involved substitution at the third position of the isatin nucleus along with chemical modification at the nitrogen atom of the scaffold to obtain more potent derivatives. The synthesized analogs were characterized by recording their melting point and R f values along with IR, NMR and mass spectra. An antioxidant study and Cytotoxic Studies were performed by DPPH, Nitric oxide scavenging method and MTT assay methods. Results: The results revealed that all the test compounds (5a-5d) exhibited good anti oxidant activity. The synthesized compounds were then screened for in-vitro cytotoxicity by MTT cell proliferation assay method against breast cancer cell lines including MCF-7 and BT-549 with derivative 5a exhibiting maximum activity in both the cell lines. DNA fragmentation studies further indicated that 5a was involved in apoptotic process. Conclusion: Interestingly, it was observed that while all the synthesized compounds seemed active, 5a exhibited a superior ability to induce apoptosis.

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Section: Assessment Of Cytotoxicity By Mtt Assaymentioning

confidence: 99%

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Sathianarayanan¹,

Chittethu²,

Jose³

et al. 2017

JYP

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“…These intermediates were then converted to compounds 4a-x using a hydrolysis-based process and then reacted with hydrazine hydrate in ethanol to yield 2-hydrazono-3-substituted phenyl-2,3-dihydroquinazolin-4(1H )-ones (5a-x). These compounds were treated with sodium nitrite and diluted hydrochloric acid at a temperature below 5 • C, and then stirred at room temperature to obtain compounds (6a-x) [14]. To obtain the target compounds 7-14, compound 5a was reacted with formic acid, acetic acid, urea, carbon disulfide, diethyl oxalate, ammonia, pyruvic acid, and acetylacetone, respectively [15][16][17][18][19][20].…”

Section: Chemistrymentioning

confidence: 99%

“…Off Synthesis of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-phenylquinazolin-4(3H)-one (14) [20] A mixture of hydrazine 5a (0.01 mol) and acetylacetone (0.012 mmol) in 1,4-dioxane (20 mL) was stirred and heated while refluxing for 3 h. The mixture was diluted in methylene chloride (10 mL) and repeatedly washed with water to remove the solvent. Finally, the organic layer was dried over anhydrous MgSO 4 , concentrated, and purified by silica gel column chromatography with CH 2 Cl 2 as the eluent to obtain compound 14.…”

Section: Synthesis Of Ethyl 5-oxo-4-phenyl-45-dihydro-mentioning

confidence: 99%

“…Among these compounds, 5-(hexyloxy)tetrazolo [1,5-a]quinazoline displayed a significant antidepressant activity and decreased the immobility times by 62.2 % at a dose of 100 mg/kg. Additionally, considerable accumulating evidence indicates that as a group, the quinazolinone derivatives possess extensive biological activities, such as antidepressant [9], anti-inflammatory [10], antimicrobial [11], anticonvulsant [12], antihelmintics [13], and anticancer [14].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antidepressant activities of 4-(substituted-phenyl)tetrazolo[1,5-a]quinazolin-5(4H)-ones and their derivatives

2015

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A series of novel 4-(substituted-phenyl) tetrazolo[1,5-a]quinazolin-5(4H)-ones (6a-x) and their derivatives with tetrazole and other heterocyclic substituents (7-14) were designed, synthesized, and evaluated for antidepressant activities in mice. Pharmacological tests showed that three compounds (6l, 6u, and 6v) at a dose of 50 mg/kg significantly reduced the immobility time in the forced swimming test. The most active compound was 4-(p-tolyl)tetrazolo[1,5-a]quinazolin-5(4H)-one (6v), which decreased the immobility time by 82.69 % at 50 mg/kg. Moreover, 6v did not affect spontaneous activity in the open-field test, and this effect was comparable to the antidepressant effect of fluoxetine. Noradrenaline (NE) and 5-hydroxytryptamine (5-HT) levels in the brains of mice in the test sample groups significantly increased at a dose of 50 mg/kg compared with that in the control group. The monoamine oxidase (MAO) level of all test groups was reduced, but this result was not significantly different between the groups. Therefore, we can infer that their underlying mechanisms may involve the regulation of brain monoamine neurotransmitter homeostasis, based on the detected content of NE, 5-HT, and MAO in mouse brain tissue.

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Synthesis and characterization of quinazolinone derivatives against mammary carcinoma

Cited by 2 publications

References 9 publications

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Synthesis and antidepressant activities of 4-(substituted-phenyl)tetrazolo[1,5-a]quinazolin-5(4H)-ones and their derivatives

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