Synthesis, anticancer evaluation, and molecular docking studies of thiazolyl-pyrazoline derivatives

Nasab, Narges Hosseini; Azimian, Fereshteh; Shim, Rok Su; Eom, Young Seok; Shah, Fahad Hassan; Kim, Song Ja

doi:10.1016/j.bmcl.2022.129105

Cited by 10 publications

(8 citation statements)

References 40 publications

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“…All chemicals were purchased from Merck or Fuluka chemical companies. 1 H-NMR 300 MHz and 13 C-NMR (75 MHz) spectra were run on a Bruker Avance 300 MHz instrument in DMSOd 6 . A Unicom Galaxy Series FT-IR 4600 spectrophotometer was used to obtain infra-red spectra.…”

Section: Generalmentioning

confidence: 99%

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Highly efficient, catalyst-free, one-pot sequential four-component synthesis of novel spiroindolinone-pyrazole scaffolds as anti-Alzheimer agents: in silico study and biological screening

Pourtaher,

Mohammadi,

Hasaninejad

et al. 2024

RSC Med. Chem.

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Section: Generalmentioning

confidence: 99%

“…Pyrazolines are one of the important classes of nitrogen heterocyclic compounds, and their analogs are of great importance in medicinal chemistry. [13][14][15] They are one of the groups of studied compounds among the azole family. Indeed, various synthesis methods and synthetic analogs have been reported over the years.…”

Section: Introductionmentioning

confidence: 99%

Highly efficient, catalyst-free, one-pot sequential four-component synthesis of novel spiroindolinone-pyrazole scaffolds as anti-Alzheimer agents: in silico study and biological screening

Pourtaher,

Mohammadi,

Hasaninejad

et al. 2024

RSC Med. Chem.

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“…[10] The pyrazole and thiazole moieties are crucial components of antiviral medications, as illustrated in Figure 1. In addition, pyrazole and thiazole have been demonstrated to exhibit broad biological activity, including anticancer, [26,27] antioxidant, [28,29] antidiabetic, [30,31] antituberculosis, [32,33] antibacterial, [34,35] antifungal, [36,37] and anticonvulsant [38,39] properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Virtual Screening of Pyrazolothiazole Conjugates as Promising SARS‐CoV‐2 Inhibitors

Seliem

2023

ChemistrySelect

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The current coronavirus outbreak has highlighted the significance of continuing to develop novel antiviral agents. The SARS‐CoV‐2 main protease (Mpro), essential for virus replication, has been recognized as a potential target for developing novel COVID‐19 therapeutics. Herein, we report synthesizing a series of pyrazolothiazole conjugates and in silico molecular docking screening of their interactions with the COVID‐19 protease 6LU7 protein. The new hybrids were obtained by condensing substituted pyrazole‐4‐carbaldehyde with N‐phenyl‐hydrazinecarbothioamide and subsequent refluxing with selected α‐haloketones in a basic medium. The structures of the novel pyrazolothiazoles were fully verified by FTIR, 1H NMR, 13C NMR, and elemental analyses. Molecular docking and free energy analyses using the MM/GBSA approach revealed that 5 a–c and 7 a–c formed stable interactions within the protease 6LU7 pocket, thus, could be potential inhibitors of SARS‐CoV‐2.

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“…Erlotinib is an FDA-approved inhibitor of EGFR . Pyrazolines, which contain a double bond and two adjacent nitrogen atoms in the ring, are five-membered heterocyclic rings and show anticancer activity. , Furthermore, the EGFR inhibition values shown by the compounds containing the 1,3,5-trisubstituted pyrazoline structure have been a guide in the design process of the compounds. , In previous studies, it was also observed that compounds containing a pyrazole ring had very good inhibition values on EGFR. , Just like the pyrazole ring, the thiadiazole ring has anticancer activity. Studies have shown that compounds containing a thiadiazole ring are pretentious about anticancer activity. − Thiadiazoles also showed anticancer activity by providing EGFR inhibition. , …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activities of Pyrazole–Thiadiazole-Based EGFR Inhibitors

Kurban,

Sağlık,

Osmaniye

et al. 2023

ACS Omega

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Lung cancer is one of the most common cancer types of cancer with the highest mortality rates. However, while epidermal growth factor receptor (EGFR) is an important parameter for lung cancer, EGFR inhibitors also show great promise in the treatment of the disease. Therefore, a series of new EGFR inhibitor candidates containing thiadiazole and pyrazole rings have been developed. The activities of the synthesized compounds were elucidated by in vitro MTT, (which is chemically 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide), cytotoxicity assay, analysis of mitochondrial membrane potential (MMP) by flow cytometry, and EGFR inhibition experiments. Molecular docking and molecular dynamics simulations were performed as in silico studies. Compounds 6d, 6g, and 6j showed inhibitor activity against the A549 cell line with IC50 = 5.176 ± 0.164; 1.537 ± 0.097; and 8.493 ± 0.667 μM values, respectively. As a result of MMP by flow cytometry, compound 6g showed 80.93% mitochondrial membrane potential. According to the results of the obtained EGFR inhibitory assay, compound 6g shows inhibitory activity on the EGFR enzyme with a value of IC50 = 0.024 ± 0.002 μM.

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Synthesis, anticancer evaluation, and molecular docking studies of thiazolyl-pyrazoline derivatives

Cited by 10 publications

References 40 publications

Highly efficient, catalyst-free, one-pot sequential four-component synthesis of novel spiroindolinone-pyrazole scaffolds as anti-Alzheimer agents: in silico study and biological screening

Highly efficient, catalyst-free, one-pot sequential four-component synthesis of novel spiroindolinone-pyrazole scaffolds as anti-Alzheimer agents: in silico study and biological screening

Synthesis and Virtual Screening of Pyrazolothiazole Conjugates as Promising SARS‐CoV‐2 Inhibitors

Synthesis and Anticancer Activities of Pyrazole–Thiadiazole-Based EGFR Inhibitors

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