Design, synthesis, and biological activity of phenyl-pyrazole derivatives as BCR–ABL kinase inhibitors

Hu, Liming; Zheng, Yuyan; Li, Zhipeng; Wang, Yujie; Lv, Yongjuan; Qin, Xuemei; Zeng, Cheng‐Chu

doi:10.1016/j.bmc.2015.04.083

Cited by 11 publications

(4 citation statements)

References 14 publications

(2 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The IC 50 values of compound 10 over Bcr-Abl kinase and K562 leukemia cell lines are 14.2 nM and 0.27 µM, respectively. Removal of trifluoromethyl group from its structure significantly decreased the potency [ 21 ].…”

Section: Pyrazole-based Bcr-abl Kinase Inhibitorsmentioning

confidence: 99%

See 1 more Smart Citation

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

et al. 2022

View full text Add to dashboard Cite

Pyrazole has been recognized as a pharmacologically important privileged scaffold whose derivatives produce almost all types of pharmacological activities and have attracted much attention in the last decades. Of the various pyrazole derivatives reported as potential therapeutic agents, this article focuses on pyrazole-based kinase inhibitors. Pyrazole-possessing kinase inhibitors play a crucial role in various disease areas, especially in many cancer types such as lymphoma, breast cancer, melanoma, cervical cancer, and others in addition to inflammation and neurodegenerative disorders. In this article, we reviewed the structural and biological characteristics of the pyrazole derivatives recently reported as kinase inhibitors and classified them according to their target kinases in a chronological order. We reviewed the reports including pyrazole derivatives as kinase inhibitors published during the past decade (2011–2020).

show abstract

Section: Pyrazole-based Bcr-abl Kinase Inhibitorsmentioning

confidence: 99%

“…The amide linker forms two more hydrogen bonds with Glu286 and Asp381. Moreover, the pyrazole ring forms pi-pi stacking interaction with Thr315 ( Figure 20 ) [ 21 ].…”

Section: Pyrazole-based Bcr-abl Kinase Inhibitorsmentioning

confidence: 99%

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

et al. 2022

View full text Add to dashboard Cite

show abstract

“…[4] Pyrazole and its derivatives are a very significant class of biologically active drugs in the pharmaceutical industry. These types of scaffolds are known for their various biological activities such as antibacterial, [5] antidiabetic, [6] antifungal, [7] anti-inflammatory, [8] antimalarial, [9] antimicrobial, [10] antioxidant, [11] antiproliferative, [12] antiviral, [13] cytotoxic, [14] anticancer, [15] Fungicides, [16] gastric secretion stimulatory, [17] herbicidal, [18] insecticides, [19] and kinase inhibitors [20] etc. Pyrazolone and pyrazole ring scaffolds are present in many drug molecules as a main structural motif such as Crizotinib, Celecoxib, Ruxolitinib, Aminophenazone, and Epirizole as shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Greener Synthetic Approach for 4,4′‐(Arylmethylene)bis(3‐methyl‐1H‐pyrazol‐5‐ol) Derivatives in an Aqueous Medium using Theophylline as a Catalyst

Pund,

Dhumal,

Deshmukh

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

Herein, we report an efficient, convenient and environmentally benign method for the synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1H‐pyrazol‐5‐ol) derivatives. The reaction of aromatic aldehydes with 3‐methyl‐1‐phenyl‐5‐pyrazolone or 5‐methyl‐2,4‐dihydro‐3H‐pyrazol‐3‐one in the presence of theophylline catalyst delivered the series of bis‐pyrazole compounds in very high yields. The method has successfully demonstrated the utility of theophylline as an expedient, eco‐friendly and green catalyst in an aqueous medium.

show abstract

“…Thiophene containing compounds are well known to exhibit various biological activities such as BACE1 inhibitors [17] and anti-breast cancer [18]. Conversely, pyrazole derivatives have been reported in the literature to demonstrate anti-tumor [19] and kinase inhibitions [20]. Motivated by these results and in continuation of our previous work aimed at the synthesis of a new heterocyclic systems for anti-tumor evaluations [21][22][23] we report here the modification of cyclohexan-1,3-dione into a variety of novel condensed pyrazole, thiophene and isoxazole derivatives incorporating the cyclohexane moiety.…”

Section: Introductionmentioning

confidence: 99%

Discovery of new thiophene, pyrazole, isoxazole derivatives as antitumor, c-Met, tyrosine kinase and Pim-1 kinase inhibitors

Mohareb¹,

Hilmy²,

Elshehawy³

2018

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

The reaction of cyclohexan-1,3-dione (1) with ethyl orthoformate (2) in acetic acid gave the 2-(ethoxymethylene)cyclohexane-1,3-dione (3). The latter compound was used for further heterocyclization reactions to give thiophene, pyrazole and pyran derivatives. The cytotoxicity of the newly synthesized compound against the six cancer cell lines NUGC, DLDI, HA22T, HEPG2, HONE1 and MCF showed that compounds 5, 10c, 10d, 13b, 14a, 18b, 18d, 18e and 20b were the most potent compounds. On the other hand, the toxicity of these compounds against shrimp larvae indicated that compounds 7a, 10c, 13b, 14a, 18b and 18d were non toxic against the tested organisms. Inhibition of the most potent compounds towards the tyrosine kinases c-kit, FIT-3, Vascular Endothelial Growth Factor Receptor (VEGFR)-2, Estimated Glomerular Filtration Rate (EGFR) and Platelet-Derived Growth Factor Receptor (PDGFR) revealed that compounds 5, 10c, 10d, 13b, 18b, 18d, 18e and 20b were of the highest inhibitory effect. The Pim-1 kinase test revealed that compounds 10d, 18b and 20b were of the highest inhibitory effect. In addition, the c-Met enzymatic activities showed that compounds 10c, 10d, 18b, 18e, 19 and 20b showed higher potencies against c-Met kinase than the reference foretinib. On the other hand, compounds 7a, 7b, 10d, 13a, 13b, 14a, 14b, 16a, 16b, 17, 18a-f, 19 and 20 showed higher inhibition towards PC-3 cell line than the reference SGI-1776. Compounds 10c and 18b were of common potencies and their molecular docking was described.

show abstract

Design, synthesis, and biological activity of phenyl-pyrazole derivatives as BCR–ABL kinase inhibitors

Cited by 11 publications

References 14 publications

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

Evaluation of Substituted Pyrazole-Based Kinase Inhibitors in One Decade (2011–2020): Current Status and Future Prospects

Greener Synthetic Approach for 4,4′‐(Arylmethylene)bis(3‐methyl‐1H‐pyrazol‐5‐ol) Derivatives in an Aqueous Medium using Theophylline as a Catalyst

Discovery of new thiophene, pyrazole, isoxazole derivatives as antitumor, c-Met, tyrosine kinase and Pim-1 kinase inhibitors

Contact Info

Product

Resources

About