Ultrasound Assisted-synthesis and Biological Evaluation of Piperazinylprop- 1-en-2-yloxy-2H-chromen-2-ones as Cytotoxic Agents

Nikalje, Anna Pratima; Tiwari, Shailee V.; Tupe, Jaydeep G.; Vyas, Vivek K.; Qureshi, Gulamnizami

doi:10.2174/1570180814666170322154750

Cited by 12 publications

(8 citation statements)

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“…Many extraction methods, such as microwave-assisted extraction (Staack and Maurer, 2003), ultrasoundassisted extraction (Anna et al, 2017), supercritical fluid extraction (Moawed et al, 2015) and ASE, have been developed, refined and applied. Among these methods, ASE, which combines elevated temperature and pressure with liquid solvents (Richter et al, 1996), is widely used because it has the ability to reduce the amount of extraction solvent required, shorten the sample preparation time and improve the extraction efficiency.…”

Section: Optimisation Of the Ase Conditionsmentioning

confidence: 99%

“…Among these methods, ASE, which combines elevated temperature and pressure with liquid solvents (Richter et al, 1996), is widely used because it has the ability to reduce the amount of extraction solvent required, shorten the sample preparation time and improve the extraction efficiency. ASE also has the advantage of a higher degree of automation compared with other methods (Anna et al, 2017;Moawed et al, 2015;Staack and Maurer, 2003). A target can be subjected to ASE as many times as needed with different solvents or different solvent ratios in the extraction, and all of these parameters can be conveniently and reliably programmed by the user.…”

Section: Optimisation Of the Ase Conditionsmentioning

confidence: 99%

“…Piperazine and its N-substituted derivatives have diverse biological activities, such as antimicrobial (Marchetti et al, 2012), antihypertensive (Glamkowski et al, 1974), anticancer (Demirci et al, 2019), anti-inflammatory (Silva et al, 2015) and analgesic (Silva et al, 2015) activities, and are widely used in the treatment of coccidiosis. However, the improper use of piperazine leads to drug residues in animal-derived foods, and the long-term consumption of these contaminated products poses a serious threat to human health (Anna et al, 2017;Lee et al, 1997;Staack and Maurer, 2003). Empirical studies have found that piperazine acts as a low-potency agonist of the extrasynaptic γ-aminobutyric acid receptors in the bag region of muscle tissue (Brennan et al, 2007), that benzylpiperazine induces a reaction sensitive to dopamine antagonists (Wada et al, 2015) and that piperazine has possible carcinogenic and brain electrophysiological effects (Lin et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

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The establishment of a practical method for the determination of piperazine residues using accelerated solvent extraction and UHPLC-FLD

Guo

Xie

Wang

et al. 2020

Qual. Assur. Saf. Crops Foods

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This article describes a reliable method for estimating piperazine residues in chicken tissues (muscle, kidney and liver) and pork via ultrahigh-performance liquid chromatography (UHPLC) coupled with a fluorescence detector (FLD) using dansyl chloride (DNS-Cl) as the derivatisation reagent. After extraction by accelerated solvent extraction (ASE), the analyte was purified on a strong cation-exchange solid-phase extraction (SPE) column. Separation was achieved using an Acquity UPLC HSS T3 (2.1 mm × 100 mm, 1.8 μm) column with ultrapure water-acetonitrile (15:85, V/V) as the mobile phase. The results showed that when the concentration of piperazine was between the limit of quantitation (LOQ) and 200.0 μg/kg, the peak area of the derivative had a good linear relationship with the piperazine concentration, and the coefficients of determination (R 2 ) were greater than or equal to 0.9991. When the spiked concentration of piperazine was equal to the LOQ, maximum residue limit (MRL) of 0.5, 1.0 and 2.0, the recoveries ranged from 79.64 to 99.77% and the relative standard deviations (RSDs) were 1.14-5.63%. The limits of detection (LODs) and LOQs were 0.50-1.20 and 1.80-3.50 μg/kg, respectively. The method was applied to the quantification of piperazine residues in commercial chicken tissues and pork from local supermarkets.

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Section: Optimisation Of the Ase Conditionsmentioning

confidence: 99%

Section: Optimisation Of the Ase Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The establishment of a practical method for the determination of piperazine residues using accelerated solvent extraction and UHPLC-FLD

Guo

Xie

Wang

et al. 2020

Qual. Assur. Saf. Crops Foods

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“…A recently marketed anticancer drug, toceranib phosphate [ 32 ] contains a 2-oxoindol-3-ylidene as well as a phosphonate moiety. The biological importance of the 2-oxoindolin-3-ylidene scaffold and α-aminophosphonates and the ongoing interest of our research group [ 16 , 33 , 34 , 35 , 36 ] in the synthesis of anticancer agents encouraged us to synthesize coupled derivatives containing isatin-based hydrazones and α-aminophosphonates with the hope of obtaining novel hybrid derivatives with better anticancer activity and minimal toxicity.…”

Section: Introductionmentioning

confidence: 99%

New 2-Oxoindolin Phosphonates as Novel Agents to Treat Cancer: A Green Synthesis and Molecular Modeling

Tiwari¹,

Sharif²,

Gajare³

et al. 2018

Molecules

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The work reports the facile synthesis of novel α-aminophosphonate derivatives coupled with indole-2,3-dione moieties, namely the diethyl(substituted phenyl/heteroaryl)(2-(2-oxoindolin-3-ylidene)hydrazinyl)methylphosphonates derivatives 4(a–n). One-pot three component Kabachnik-Fields reactions were used to synthesize these derivatives. The reaction was carried out at room temperature by stirring in presence of ceric ammonium nitrate (CAN) as a green catalyst. The structures of the synthesized compounds were established by spectral studies. The synthesized derivatives 4(a–n) were evaluated for their in vitro anticancer activity against six human cancer cell lines by the SRB assay method. The cancer cell lines used in this research work are SK-MEL-2 (melanoma), MCF-7 (breast cancer), IMR-32 (neuroblastoma) MG-63 (human osteosarcoma), HT-29 (human colon cancer) and Hep-G2 (human hepatoma). All the synthesized derivatives inhibited the cell proliferation. Importantly, all the target compounds showed no cytotoxicity towards normal tissue cells (GI50 > 250 µM). A docking study was performed to predict the mode of action. Docking results indicate that the compounds have good binding with the enzyme tyrosine kinase as well as with microtubules, which makes them dual inhibitors. The result of in-silico bioavailability studies suggests that the compounds from the present series have good oral drug-like properties and are non-toxic in nature. In vivo acute oral toxicity study results indicate that the compounds can be considered safe, and therefore could be developed in the future as good anticancer agents or as leads for the design and synthesis of novel anticancer agents.

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“…However, our literature survey indicated that the potential in vitro anticancer activity of pyranopyazoles against SK-MEL-2, MDA-MB-231, K-562 and HeLa had not yet explored for, therefore, the above cell lines were selected for anticancer evaluation. In continuation of our search for green synthesis methods for novel heterocycles as anticancer agents [ 22 , 23 , 24 ] we report herein the ionic liquid-assisted multi-component synthesis of ten dihydropyrano[2,3- c ]pyrazoles derivatives. The research protocol was designed taking into consideration the existing anticancer drugs containing a pyrazole ring as an important pharmacophore.…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

Nimbalkar¹,

Seijas

Vázquez-Tato

et al. 2017

Molecules

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A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.

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Ultrasound Assisted-synthesis and Biological Evaluation of Piperazinylprop- 1-en-2-yloxy-2H-chromen-2-ones as Cytotoxic Agents

Cited by 12 publications

References 0 publications

The establishment of a practical method for the determination of piperazine residues using accelerated solvent extraction and UHPLC-FLD

The establishment of a practical method for the determination of piperazine residues using accelerated solvent extraction and UHPLC-FLD

New 2-Oxoindolin Phosphonates as Novel Agents to Treat Cancer: A Green Synthesis and Molecular Modeling

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

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