Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

doi:10.3390/ijms17091499

Paper

Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

Published Sep 1, 2016 · Sobhi M. Gomha, M. M. Edrees, Farag M. A. Altalbawy

International Journal of Molecular Sciences

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Abstract

A new series of 1,4-bis(1-(5-(aryldiazenyl)thiazol-2-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)benzenes 3a–i were synthesized via reaction of 5,5′-(1,4-phenylene)bis(3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide) (1) with hydrazonoyl halides 2a–i. In addition, reaction of 1 with ethyl chloroacetate afforded bis-thiazolone derivative 8 as the end product. Reaction of compound 8 with methyl glyoxalate gave bis-thiazolone derivative 10. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. All the synthesized compounds were evaluated for their anti-tumor activities against hepatocellular carcinoma (HepG2) cell lines, and the results revealed promising activities of compounds 3g, 5e, 3e, 10, 5f, 3i, and 3f with IC50 equal 1.37 ± 0.15, 1.41 ± 0.17, 1.62 ± 0.20, 1.86 ± 0.20, 1.93 ± 0.08, 2.03 ± 0.25, and 2.09 ± 0.19 μM, respectively.

In Vitro Study

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Study Snapshot

New bis-pyrazolyl-thiazoles with thiophene moiety show promising anti-tumor activities against hepatocellular carcinoma (HepG2) cell lines.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

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Citations

Insight into the therapeutic potential of pyrazole-thiazole hybrids: A comprehensive review.

Pyrazle-thiazole hybrids show diverse pharmacological activities, including anticancer, antifungal, antibacterial, analgesic, and anti-inflammatory properties, offering potential for developing more effective treatments.

Green Biocatalyst for Ultrasound-Assisted Thiazole Derivatives: Synthesis, Antibacterial Evaluation, and Docking Analysis

Ultrasound-assisted thiazole derivatives synthesized using TCsSB as an eco-friendly biocatalyst show promising antibacterial effectiveness and favorable pharmacological properties.

Antimicrobial Activity of Novel Ni(II) and Zn(II) Complexes with (E)-2-((5-Bromothiazol-2-yl)imino)methyl)phenol Ligand: Synthesis, Characterization and Molecular Docking Studies

The novel Ni(II) complex with (E)-2-((5-Bromothiazol-2-yl)imino)methyl)phenol ligand shows potent antibacterial activity against selective bacteria, outperforming other compounds and Streptomycin.

Green Synthesis and Molecular Docking Study of Some New Thiazoles Using Terephthalohydrazide Chitosan Hydrogel as Ecofriendly Biopolymeric Catalyst

Terephthalohydrazide chitosan hydrogel (TCs) is a promising ecofriendly biocatalyst for synthesis of novel thiazole and thiadiazole derivatives, offering mild reaction conditions, quick reaction durations, and high reaction yields.

Molecular dynamics simulation approach of hybrid chalcone–thiazole complex derivatives for DNA gyrase B inhibition: lead generation

The study generated lead compound 178, a promising candidate for developing novel drugs against tuberculosis infections, through molecular docking and dynamics simulation studies.

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Bis-chalcones show potential in anti-inflammatory activity, with recent developments in synthetic methods and active structures.