Optimization of antimalarial, and anticancer activities of (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate

Romero, Jesús; Acosta, María Eugenia; Gamboa, Neira; Mijares, Michael R.; Sanctis, Juan B. De; Charris, Jaime

doi:10.1016/j.bmc.2017.12.022

Cited by 22 publications

(36 citation statements)

References 34 publications

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“…Quinoline derivatives are largely used in the pharmaceutical chemistry owing to the wide range of applications. Quinoline derivatives possess various biological activities such as antiviral , anticancer , antibacterial , antifungal , anti‐obesity , anti‐inflammatory , antimalarial , antituberculosis , hypnotic , antischizophrenic , anti‐protozoal , anti‐cholesterol , anthelmintic , and analgesic activities , and these activities were demonstrated in drug molecules, which are shown in Figure . At present, a wide range of microorganism such as fungi, viruses, and bacteria are becoming resistant against drugs that are used to treat infectious diseases.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological andIn SilicoStudy of Fluorine‐Containing Quinoline Hybrid Thiosemicarbazide Analogues

Patel

Prajapati

et al. 2019

Journal of Heterocyclic Chem

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A novel series of fluorine‐containing quinoline hybrid thiosemicarbazide analogues (8a–8l) were synthesized and tested for their biological activities. The antibacterial results demonstrated that compounds 8d and 8l [minimal inhibitory concentration (MIC) 62.5 μg/mL] were shown to have higher biological activity than ampicillin against Escherichia coli. Compound 8b (MIC 25 μg/mL) was shown to have the highest activity than was ampicillin against Staphylococcus aureus. The antifungal results demonstrated that compound 8j (MIC 100 μg/mL) has shown good activity. Most of the targeted compounds have shown potent antimalarial activity. Compounds 8d (0.19 μg/mL), 8g (0.30 μg/mL), 8h (0.36 μg/mL), 8k (0.10 μg/mL), 8l (0.28 μg/mL), 8k (0.10 μg/mL), and 8l (0.28 μg/mL) have notable activity than does the reference drug quinine. Compounds 8d (0.27 μg/mL), 8g (0.30 μg/mL), and 8k (0.17 μg/mL) have shown excellent activity against chloroquine‐resistant strain. The MTT assay performed on peripheral blood lymphocyte cultures showed a high percentage of lymphocyte viability [8d (99.64), 8g (99.46), 8h (98.83), and 8k (99.51)] at a maximum dose (10 μg/mL), depicting no cytotoxicity of these compounds on human lymphocytes in vitro. A molecular docking study was performed on Pf‐DHFR‐TS inhibitor. A molecular dynamics study has shown compound 8g to have better affinity with protein. ADME‐Tox and pharmacophore study of synthesized compounds suggested prediction of active site.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological andIn SilicoStudy of Fluorine‐Containing Quinoline Hybrid Thiosemicarbazide Analogues

Patel

Prajapati

et al. 2019

Journal of Heterocyclic Chem

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“…Esterification of phenolic-OH of 2-quinoline-thioester scaffolds with various aromatic carboxylic acids afforded a novel series of quinoline-thioesters and subsequently their anticancer properties were explored. [96] Compared to Doxorubicin (IC 50 = 1.03 μM), the anticancer assessment values indicate moderate to poor inhibitory potencies. Amongst a few decent anticancer agents, trimethoxy benzoic acid analogs have emerged as potent molecules.…”

Section: Phosphorous Silicon and Sulfur-containing Quinoline Analogsmentioning

confidence: 99%

“…Sulfur and Silicon containing anticancer quinoline molecules B. [95][96][97][98][99] potent MCF-7 inhibitory properties with IC 50 values of 38.…”

Section: Phosphorous Silicon and Sulfur-containing Quinoline Analogsmentioning

confidence: 99%

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Dorababu¹

2020

ChemistrySelect

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Quinoline has been a most essential pharmacophore, derivatization of which led to enticing pharmacological properties. Quinoline is responsible for a wide range of biological potencies such as antibacterial, antifungal, anti-leishmanial, antimalarial, antioxidant and anticancer properties. Out of these clinical importances, the anticancer property of heterocycles is of greatest concern as cancer has become a major threat globally. Since some natural products containing quinoline moiety have displayed cancer inhibition potency, quinoline has been given highest priority in the anticancer drug design and development. In addition, quinoline has got eight positions including nitrogen for substitution which may result in some potential anticancer properties. Ever since, this extraordinary potential is being utilized in anticancer drug discovery. In this review, the various trends in drug design of quinoline moiety anticipating finest anticancer properties through cancer cell growth inhibition are collated comprehensively. The review work is classified based on type of quinoline derivatives. Besides this, with the aid of structure-activity relationship discussion, the importance of structural units that contributed to strongest activity towards cancer inhibition is emphasized. The particular activity would help to bring further advanced anticancer agents in the future.

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“…The assay was performed according to previously reported protocols. 26,29,35 Hemin chloride (50 µL, 4 mM) in DMSO (5.2 mg mL −1 ) was pipetted into 96-well microplates. Different concentrations (5-100 mM) of the compounds in DMSO were added in triplicate (50 µL).…”

Section: Antimalarial Activitymentioning

confidence: 99%

“…[12][13][14][15][16][17] A further approach refers to a superimposition in a single molecular scaffold of the structural features responsible for the activity of different antimalarial and anticancer agents. [18][19][20][21][22][23] In our previous reports, [24][25][26][27] different quinoline compounds were designed and synthesized. The in vitro and in vivo biological activities of these compounds showed promising potential as antimalarial and anticancer compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives as antimalarial and cytotoxic agents

Ramírez

Rodrígues

Mijares

et al. 2020

Journal of Chemical Research

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A novel series of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]- N-phenylacetamide derivatives is synthesized via substitution with 2-mercapto-4-methyl-5-thiazoleacetic acid at position 4 of 4,7-dichloroquinoline to obtain an intermediate acetic acid derivative. The chemical behavior of these reactants was investigated using different reaction conditions to optimize the nucleophilic substitution at position 4. The final compounds are prepared using a modified version of the Steglich esterification reaction between the acetic acid intermediate 3 and different anilines. The structures are confirmed by infrared, 1H, 13C, distortionless enhancement by polarization transfer 135°, Correlated Spectroscopy, heteronuclear correlation spectroscopy and (Long range HETCOR using three BIRD pulses) FLOCK-NMR spectral studies, and by elemental analysis. The synthesized compounds are tested in vitro and in vivo for their potential antimalarial and anticancer activities, with derivative 11 being the most promising candidate.

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Optimization of antimalarial, and anticancer activities of (E)-methyl 2-(7-chloroquinolin-4-ylthio)-3-(4-hydroxyphenyl) acrylate

Cited by 22 publications

References 34 publications

Design, Synthesis, and Biological andIn SilicoStudy of Fluorine‐Containing Quinoline Hybrid Thiosemicarbazide Analogues

Design, Synthesis, and Biological andIn SilicoStudy of Fluorine‐Containing Quinoline Hybrid Thiosemicarbazide Analogues

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Synthesis and biological activity of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives as antimalarial and cytotoxic agents

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