Design, synthesis and biological evaluation of novel (E)-N-phenyl-4-(pyridine-acylhydrazone) benzamide derivatives as potential antitumor agents for the treatment of multiple myeloma (MM)

Li, Xinyang; Li, Shuai; Lu, Guoqing; Wang, De-pu; Liu, Kai-li; Qian, Xin-hua; Xue, Wen-han; Meng, Fan‐hao

doi:10.1016/j.bioorg.2020.104189

Cited by 12 publications

(5 citation statements)

References 21 publications

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“…The X-ray diffraction (XRD) measurement was performed to study the crystallinity and nanostructure features of the native chitosan and the chitosan-La 2 O 3 (15 wt%) thin film nanocomposites. In Figure 5 , the XRD of blank chitosan (A) shows the main characteristic broad peak at 2θ = 20°, which indicates the presence of crystalline and amorphous regions in chitosan as reported in the literature [ 12 ]. Moreover, the purity of chitosan was confirmed by the absence of any additional peaks of impurities in the pattern.…”

Section: Resultssupporting

confidence: 56%

“…Extending our earlier efforts in the area of nanocatalysis [ 5 , 6 , 7 ], in this article La 2 O 3 nanoparticles immobilized onto the chitosan matrix were prepared ( Figure 1 ) and then employed as a promising heterogeneous basic catalyst to synthesis pyridines and pyrazoles. These azines and azoles have privileged antitumor [ 12 , 13 , 14 , 15 ], antidiabetes [ 16 ], antimicrobial [ 17 , 18 ], anti-HCV [ 14 , 19 , 20 ], and antidepressant [ 21 , 22 ] activities.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Chitosan-La2O3 Nanocomposite and Its Utility as a Powerful Catalyst in the Synthesis of Pyridines and Pyrazoles

et al. 2021

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Recently, the development of nanocatalysts based on naturally occurring polysaccharides has received a lot of attention. Chitosan (CS), as a biodegradable and biocompatible polysaccharide, is considered to be an excellent template for the design of a hybrid biopolymer-based metal oxide nanocomposite. In this case, lanthanum oxide nanoparticles doped with chitosan at different weight percentages (5, 10, 15, and 20 wt% CS/La2O3) were prepared via a simple solution casting method. The prepared CS/La2O3 nanocomposite solutions were cast in a Petri dish in order to produce the developed catalyst, which was shaped as a thin film. The structural features of the hybrid nanocomposite film were studied by FTIR, SEM, and XRD analytical tools. FTIR spectra confirmed the presence of the major characteristic peaks of chitosan, which were modified by interaction with La2O3 nanoparticles. Additionally, SEM graphs showed dramatic morphological changes on the surface of chitosan, which is attributed to surface adsorption with La2O3 molecules. The prepared CS/La2O3 nanocomposite film (15% by weight) was investigated as an effective, recyclable, and heterogeneous base catalyst in the synthesis of pyridines and pyrazoles. The nanocomposite used was sufficiently stable and was collected and reused more than three times without loss of catalytic activity.

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Section: Resultssupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

Synthesis of Chitosan-La2O3 Nanocomposite and Its Utility as a Powerful Catalyst in the Synthesis of Pyridines and Pyrazoles

et al. 2021

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“…1 H– 1 H homonuclear NOESY spectrum discovered a NOE signal which is assigned between two protons; H 1 (CH = N, δ = 8.18 ppm) and H 2 (NH-N = C, δ = 11.39 ppm), which is in agreement with the E -isomer ( E - 6i ) configuration and is not tolerable in the putative ( Z - 6i ) attributable to the larger intramolecular H-H distance of Z -isomer as demonstrated in Figure 4 . Therefore, target compounds in series ( I ) and ( II ) are established as the E -isomers 40 , 41 .…”

Section: Resultsmentioning

confidence: 99%

Discovery of novel enasidenib analogues targeting inhibition of mutant isocitrate dehydrogenase 2 as antileukaemic agents

Khalil

El‐Moselhy

El-Bastawissy

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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Mutant isocitrate dehydrogenase (IDH) 2 “IDH2m” acquires a neo-enzymatic activity reducing α-ketoglutarate to an oncometabolite, D-2-hydroxyglutarate (2-HG). Three s -triazine series were designed and synthesised using enasidenib as a lead compound. In vitro anticancer screening via National Cancer Institute “NCI” revealed that analogues 6a, 6c , 6d , 7g, and 7l were most potent, with mean growth inhibition percentage “GI%” = 66.07, 66.00, 53.70, 35.10, and 81.15, respectively, followed by five-dose screening. Compounds 6c, 6e, and 7c were established as the best IDH2 R140Q inhibitors compared to enasidenib, reporting IC 50 = 101.70, 67.01, 88.93, and 75.51 nM, respectively. More importantly, 6c, 6e, and 7c displayed poor activity against the wild-type IDH2, IC 50 = 2928, 2295, and 3128 nM, respectively, which implementing high selectivity and accordingly safety. Furthermore, 6c was screened for cell cycle arrest, apoptosis induction, and western blot analysis. Finally, computational tools were applied to predict physicochemical properties and binding poses in IDH2 R140Q allosteric site.

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“…The effect of the hydrazones on RPMI8226 cells was also noticeably superior to that on U266 cells after being replaced by 4‐Cl‐3‐CF 3 . [ 65 ]…”

Section: N‐acylhydrazones As Anticancer Agentsmentioning

confidence: 99%

“…The effect of the hydrazones on RPMI8226 cells was also noticeably superior to that on U266 cells after being replaced by 4-Cl-3-CF 3 . [65] The in vitro cytotoxic effects of two series of carbazole compounds against the three cell lines A875, HepG2, and MARC145 were assessed. Compared to the control 5-fluorouracil (5-FU), the results showed that some of these carbazole derivatives had much better cytotoxic effects against the examined cell lines.…”

Section: N-acylhydrazones As Apoptosis Inducersmentioning

confidence: 99%

Anticancer agents incorporating the N‐acylhydrazone scaffold: Progress from 2017 to present

Kassab

2023

Archiv der Pharmazie

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The N-acylhydrazone motif has been shown to be particularly adaptable and promising in the area of medicinal chemistry and drug development, due to its significant biological and pharmacological characteristics. Moreover, N-acylhydrazones are appealing synthetic and biological tools because of their simple and straightforward synthesis. This scaffold has emerged as a fundamental building block for the synthesis of bioactive compounds.Particularly, the N-acylhydrazone scaffold served as a base for the synthesis of a number of potent anticancer agents acting via different mechanisms. An updated summary of the anticancer activity of N-acylhydrazone derivatives described in the literature (from 2017 to 2022) is provided in the current review. It discusses the structure-activity relationship (SAR) of N-acylhydrazone derivatives exhibiting anticancer potential, which could be helpful in designing and developing new derivatives as effective antiproliferative candidates in the future.

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Design, synthesis and biological evaluation of novel (E)-N-phenyl-4-(pyridine-acylhydrazone) benzamide derivatives as potential antitumor agents for the treatment of multiple myeloma (MM)

Cited by 12 publications

References 21 publications

Synthesis of Chitosan-La2O3 Nanocomposite and Its Utility as a Powerful Catalyst in the Synthesis of Pyridines and Pyrazoles

Synthesis of Chitosan-La2O3 Nanocomposite and Its Utility as a Powerful Catalyst in the Synthesis of Pyridines and Pyrazoles

Discovery of novel enasidenib analogues targeting inhibition of mutant isocitrate dehydrogenase 2 as antileukaemic agents

Anticancer agents incorporating the N‐acylhydrazone scaffold: Progress from 2017 to present

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