New Chalcone-Type Compounds and 2-Pyrazoline Derivatives: Synthesis and Caspase-Dependent Anticancer Activity

Chouiter, Mohamed Imed; Boulebd, Houssem; Pereira, David M.; Valentão, Patrı́cia; Belfaitah, Ali; Silva, Artur M. S.

doi:10.4155/fmc-2019-0342

Cited by 36 publications

(25 citation statements)

References 58 publications

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“…Apart from these efforts, a very limited number of related compounds have been prepared and reported which, however, have either shown no activity at all, being far less active than their precursors [ 139 ], or they display IC 50 values over 40 μM against tested cell lines [ 140 ], or, in some cases, their activities are not reported at all, presumably due to the lack of it [ 141 ]. Nevertheless, compound 63 ( Figure 22 ) incorporating a structurally interesting imidazoquinonyl moiety has shown low cytotoxicity against HeLa cancer cells (IC 50 = 15.1 μM), slightly higher than its chalcone precursor or N -phenyl pyrazoline analogue [ 142 ].…”

Section: 2-pyrazolinesmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

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Pyrazolines are five-membered heterocycles possessing two adjacent nitrogens. They have attracted significant attention from organic and medicinal chemists due to their potent biological activities and the numerous possibilities for structural diversification. In the last decade, they have been intensively studied as targets for potential anticancer therapeutics, producing a steady yearly rise in the number of published research articles. Many pyrazoline derivatives have shown remarkable cytotoxic activities in the form of heterocyclic or non-heterocyclic based hybrids, such as with coumarins, triazoles, and steroids. The enormous amount of related literature in the last 5 years prompted us to collect all these published data from screening against cancer cell lines, or protein targets like EGFR and structure activity relationship studies. Therefore, in the present review, a comprehensive account of the compounds containing the pyrazoline nucleus will be provided. The chemical groups and the structural modifications responsible for the activity will be highlighted. Moreover, emphasis will be given on recent examples from the literature and on the work of research groups that have played a key role in the development of this field.

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Section: 2-pyrazolinesmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

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“…Chouiter et al synthesized chalcones and pyrazoline-type compounds based on an imidazole or benzimidazole core and evaluated the anticancer activity of these compounds against A549 adenocarcinoma and AGS stomach cancer cell lines; counter-screening was also performed against the MRC-5 human lung fibroblast cell line [181] Rasal et al synthesized compounds containing a dimethylpyrrole carboxamidebenzimidazole scaffold as potential anticancer agents that were evaluated against the NCI 60 cancer cell line panel [184]. When tested at a concentration of 10 µM, compound 214 displayed the highest growth inhibition of 62.46% against the MDA-MB-435 and 40.24% against the MDA-MB-468 cell lines.…”

Section: Benzimidazole Containing and Related Moleculesmentioning

confidence: 99%

Section: Anticancer Activities Shown By Imidazole Derivatives Through Undefined Mechanismsmentioning

confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives as anticancer agents appearing in the peer-reviewed literature from 2018 through 2020. Such molecules have been shown to modulate various targets, including microtubules, tyrosine and serine-threonine kinases, histone deacetylases, p53-Murine Double Minute 2 (MDM2) protein, poly (ADP-ribose) polymerase (PARP), G-quadraplexes, and other targets. Imidazole-containing compounds that display anticancer activity by unknown/undefined mechanisms are also described, as well as key features of structure-activity relationships. This review is intended to provide an overview of recent advances in imidazole-based anticancer drug discovery and development, as well as inspire the design and synthesis of new anticancer molecules.

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“…Sf9 cells were plated at the same density described for viability studies and exposed to the molecules under study for the designated time. Generally, the same method described by the authors previously for mammalian cells [39] was used; however, it was adapted for insect cells. After the incubation period, caspase-3/7 substrate was added to wells and cells incubated for 20 min at 22 • C. The luminescent signal was measured in a microplate reader (Cytation 3, BioTek, Winooski, VT, USA), and was performed in duplicate in three independent experiments.…”

Section: Caspase-like Activitymentioning

confidence: 99%

New Eugenol Derivatives with Enhanced Insecticidal Activity

Fernandes

Pereira

et al. 2020

IJMS

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Eugenol, the generic name of 4-allyl-2-methoxyphenol, is the major component of clove essential oil, and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant actions. New O-alkylated eugenol derivatives, bearing a propyl chain with terminals like hydrogen, hydroxyl, ester, chlorine, and carboxylic acid, were synthesized in the present work. These compounds were later subjected to epoxidation conditions to give the corresponding oxiranes. All derivatives were evaluated against their effect upon the viability of insect cell line Sf9 (Spodoptera frugiperda), demonstrating that structural changes elicit marked effects in terms of potency. In addition, the most promising molecules were evaluated for their impact in cell morphology, caspase-like activity, and potential toxicity towards human cells. Some molecules stood out in terms of toxicity towards insect cells, with morphological assessment of treated cells showing chromatin condensation and fragmentation, which are compatible with the occurrence of programmed cell death, later confirmed by evaluation of caspase-like activity. These findings point out the potential use of eugenol derivatives as semisynthetic insecticides from plant natural products.

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New Chalcone-Type Compounds and 2-Pyrazoline Derivatives: Synthesis and Caspase-Dependent Anticancer Activity

Cited by 36 publications

References 58 publications

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

New Eugenol Derivatives with Enhanced Insecticidal Activity

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