Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action

Charris, Jaime; Monasterios, Melina; Acosta, María Eugenia; Rodríguez, Miguel Ángel; Gamboa, Neira; Martínez, Gricelis; Rojas, Héctor; Mijares, Michael R.; Sanctis, Juan B. De

doi:10.1007/s00044-019-02435-0

Cited by 28 publications

(15 citation statements)

References 55 publications

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“…More recently, Charris et al prepared and screened a number of closely related to 20 quinoline-pyrazoline hybrids with the main difference of the absence of a substituent at the nitrogen-1 of the pyrazoline ring [ 71 ]. Compound 21 ( Figure 10 ) exhibited the best selectivity profile (human leukemia cells vs. human lymphocytes) with IC 50 values of 3.17, 0.94, and 45.92 μM (24 h) against Jurkat E6.1, HL60, and normal lymphocytes.…”

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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“…Most of the 7-chloroquinoline chalcones and corresponding pyrazole analogs constituting four series of derivatives have exhibited promising β-hematin formation inhibitory properties. [8] The promising β-HF inhibitors were selectively chosen to determine the parasitemia percentages. Towards 3D7 and K1 strains of P. falciparum, the inhibitory properties of chiral chloroquine derivatives were determined.…”

Section: Antimalarial Activity and Quinoline Inhibitorsmentioning

confidence: 99%

“…Structures of quinoline derivatives with remarkable antimalarial activity. [8][9][10][11][12] A patent file reviewing the structural modification of chloroquine at quinoline 4-position leading to compound 28 ( Figure 3) [11] is utilized for further antimalarial potency investigation towards the drug-resistant strains of P. falciparum and P. berghei. [12] The chloroquine analog has endorsed with excellent P. falciparum properties towards 3D7 (IC 50 = 18.95 nM) and W2 (IC 50 = 304.57 nM) strains which are better than parent compound (3D7, IC 50 = 21.55 nM and W2, IC 50 = 440.92 nM); while promising CQ40 inhibitory (ED 50 = 26.5 nM) has been bestowed by the compound 28 compared to Chloroquine (ED 50 = 210 nM).…”

Section: Antimalarial Activity and Quinoline Inhibitorsmentioning

confidence: 99%

Quinoline: A Promising Scaffold in Recent Antiprotozoal Drug Discovery

Dorababu¹

2021

ChemistrySelect

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Protozoal infections malaria and leishmania have become most prevalent in recent times. A high death rate is reported world‐wide because of these diseases. Although there are only a few antiprotozoal drugs but could not be used anymore to cure protozoal diseases because of their toxic effects. Despite the non‐ceasing attempts to discover the drugs to cure malaria and leishmania, efficient drug‐design with low toxicity could not be achieved. A wide range of heterocyclic pharmacophores have been utilized to design efficient drugs. Amongst these heterocycles, quinoline bicycle is given a high priority, since a vast literature of quinoline derivatives relevant to potent pharmacological properties is available. The efficacy of the drugs lies upon the good bioavailability, favorable pharmacokinetics, and pharmacodynamics of the molecule. In view of these, the continual efforts are being put to bring about potent anti‐protozoal agents to clinical stage. In this review, the potential research done recently towards the anti‐protozoal drug‐design and discovery is compiled comprehensively. The importance of structural features attributed to remarkable activity is described taking consideration of structure‐activity relationship. Safety Index (SI), crucial for clinical efficiency of a drug is compared amongst a set of derivatives which involve inhibitory properties, in addition to the cytotoxic effects.

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“…In the last few years, we have aimed to design new potent antimalarial and anticancer agents. [ 28–32 ] To increase the biological effect, we used molecular hybridization to produce new 7‐chloroquinoline derivatives. These derivatives contain thiazole‐tethered functional hydrazides scaffolds, where the bridge that joins it to the aromatic ring has been extended with a couple of atoms incorporating on the aromatic group electron‐donating groups such as OH, OMe, and OPhe that have been effective in these types of biological assays.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimalarial and anticancer evaluation of 7‐chlorquinoline‐4‐thiazoleacetic derivatives containing aryl hydrazide moieties

Ramírez

Fernández

Rodrígues

et al. 2021

Archiv der Pharmazie

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Twelve 7‐chloroquinoline derivatives were designed and synthesized using the principle of molecular hybridization through the coupling of 2‐[2‐(7‐chloroquinolin‐4‐ylthio)‐4‐methylthiazol‐5‐yl]acetic acid 1 with various benzoyl hydrazines 2a–l. The synthetic compounds were tested as antimalarials. Some of them showed an efficient in vitro activity as inhibitors of β‐hematin formation and an in vivo activity in a murine model, resulting in compounds 8 and 9 as the most active ones with IC50 values of 0.65 ± 0.09 and 0.64 ± 0.16 µM, respectively. The effects of the compounds on the cell viability, cell cycle, and apoptosis induction of A549 and MCF‐7 cancer cell lines were also examined. Our data showed that compounds 6 and 12 were the most active agents, decreasing the cell viability of MCF‐7 cells with IC50 values of 15.41 and 12.99 µM, respectively. None of the compounds analyzed significantly affected the viability of peripheral blood mononuclear cells. Also, significant induction of apoptosis was observed when both cancer cell lines were incubated with compounds 6 and 12. In MCF‐7 cells, treatment with these compounds led to cell cycle arrest in the G0/G1 phase. The results obtained suggest that these structures may be useful in developing new therapies for malaria and cancer treatment.

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Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action

Cited by 28 publications

References 55 publications

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

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

Quinoline: A Promising Scaffold in Recent Antiprotozoal Drug Discovery

Synthesis and antimalarial and anticancer evaluation of 7‐chlorquinoline‐4‐thiazoleacetic derivatives containing aryl hydrazide moieties

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