Current scenario of pyrazole hybrids with in vivo therapeutic potential against cancers

Xu, Zhi; Zhuang, Yafei; Chen, Qingtai

doi:10.1016/j.ejmech.2023.115495

Cited by 22 publications

(8 citation statements)

References 116 publications

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“…The uncontrolled proliferation of tumor cells within the human body underscores the persistent threat posed by cancer. Despite the employment of numerous therapeutic modalities, there exists an urgent imperative to discover novel anticancer agents (Astrain-Redin et al, 2023;Song et al, 2021;Xu, Luo, et al, 2023;Xu, Zhuang, et al, 2023).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and anticancer evaluation of alkynylated pyrrole derivatives

Wei,

Cao,

Zhao

et al. 2024

Chem Biol Drug Des

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A series of alkynylated pyrrole derivatives were meticulously designed, drawing inspiration from the structure of 3‐alkynylpyrrole‐2,4‐dicarboxylates, which were synthesized via a cyclization process involving methylene isocyanides and propiolaldehydes under mild conditions. These derivatives were subsequently subjected to evaluation for their anticancer properties against a panel of cell lines, including U251, A549, 769‐P, HepG2, and HCT‐116. According to the detailed analysis of structure–activity relationship, compound 12l emerged as the most promising molecule, with IC50 values of 2.29 ± 0.18 and 3.49 ± 0.30 μM toward U251 and A549 cells, respectively. Subsequent mechanistic investigations revealed that compound 12l exerts its effects by arresting the cell cycle in the G0/G1 phase and inducing apoptosis specifically in A549 cells. These innovative alkynylated pyrrole derivatives hold the potential to serve as a valuable template for the discovery of novel anticancer molecules.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, and anticancer evaluation of alkynylated pyrrole derivatives

Wei,

Cao,

Zhao

et al. 2024

Chem Biol Drug Des

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“…Their derivatives are useful in agriculture, [1] polymeric materials [2] and in optoelectronics. [3] To understand the domain of applications; these molecules play an integral role in the core structures of different antiviral, [4] anti-tuberculosis, [5] anti-HIV, [6] anticancer, [7] antiobesity, [8] antiproliferative [9] agents and other therapeutic drug candidates as well. [10,11] Diabetes mellitus (DM), a silent killer, is a disorder of carbohydrate metabolism and α-glucosidase is considered as one of the attractive targets to manage the sudden postprandial increase in blood sugar levels of diabetic patients.…”

Section: Introductiomentioning

confidence: 99%

Synthesis, in vitro α‐Glucosidase Inhibition, DFT Calculations, and Molecular Docking Studies of Some New Substituted 2,5‐Bis(pyrazolyl)‐1,3,4‐oxadiazoles

Chaudhry,

Abdullah,

un‐Nisa

et al. 2024

ChemistrySelect

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A pivotal feature of present research study is the synthesis of some new 2,5‐bis(pyrazolyl)‐1,3,4‐oxadiazoles as promising α‐glucosidase inhibitors. In this regard, a facile reaction scheme was designed to afford 1,3,4‐oxadiazole ring. In search of the most favourable reaction condition, a model reaction was first carried out between 1,3‐diphenyl‐1H‐pyrazole‐4‐carbohydrazide (3) and 1,3‐diphenyl‐1H‐pyrazole‐4‐carboxylic acid (4 a) using phosphorous oxychloride (POCl3). The results emanated from this model reaction were utilized to prepare other derivatives to highlight the scope of current synthetic approach and the structures of the prepared molecules were characterized from spectroscopic techniques. These derivatives were further investigated for their α‐glucosidase inhibitory potentials. 2,5‐Bis(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole (5 a) and 2‐(3‐(4‐bromophenyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)‐5‐(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole (5 c) displayed strong in vitro inhibitory activities with IC50 73.1±1.13 μM and IC50 87.3±1.12 μM respectively with least toxicity profiles. Molecular docking and computational studies including geometry optimization of synthesized molecular systems, calculations of their orbital energies, and molecular electrostatic potential (MEP) surface maps further helped to establish structural and electronic properties contributing towards their bioactivity. The electrophilicity index significantly quantifies the biological activity. The experimental and computational data altogether facilitated in understanding the therapeutic attributes of these versatile scaffolds in relation to their α‐glucosidase inhibition.

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“…[13,14] Additionally, pyrazole derivatives, in particular, pyrazole hybrids, showed significant anti-tumor capabilities both in vivo and in vitro by triggering apoptosis, regulating autophagy, and interfering with the cell cycle. [15] Consequently, the goal of the current work is to synthesize novel heterocyclic compounds with potential biological effects. This can be achieved by using 3,5-dimethyl-1H-pyrazole-1carbothiohydrazide as a significant precursor for the accessible one-pot synthesis of novel pyrazole derivatives, and then testing their anti-tumor efficacy.…”

Section: Introductionmentioning

confidence: 99%

Convenient One‐Pot Synthesis and Biological Evaluation of New 3,5‐Dimethyl‐1H‐pyrazole‐1‐carbothiohydrazide Derivatives as Anti‐Tumor Agents

Fouad,

Elaasser

2024

ChemistrySelect

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Pyrazole compounds have garnered attention due to their potential biological and medicinal qualities. Therefore, the purpose of the research being described is to utilize 3,5‐dimethyl‐1H‐pyrazole‐1‐carbothiohydrazide (1) as a starting material in a one‐pot synthesis to create novel pyrazole derivatives with potential biological applications. When either ethanol or acetic acid was added, components 1 and 1,3‐diphenylpropane‐1,3‐dione (2) reacted to produce derivative 3. Compound 1, when combined with ethanol, chemical 2, or acetyl acetone 5 and triethylamine, yielded chemicals 4 and 6 respectively. When ingredient 1 was mixed with ethyl cyanoacetate (7), stearic acid (10), or carboxylic acids 12 a–c, 9, 11, and 13 a–c were formed as a result. The equivalent 1,3,4‐thiadiazine derivatives, 15 and 17, were produced when 1 was mixed with either 14 or 16. The developed compounds′ cytotoxic properties were evaluated against lung and liver cancer. Our research identified a number of interesting bioactive chemicals, among which chemical 17 exhibited the greatest effectiveness against lung and liver cancer as well as the highest selectivity index measurements. It indicated a strong IC50 value of 5.35 and 8.74 μM, accordingly, when compared with 3.78 and 6.39 μM for the reference medication cisplatin. Additionally, its safety for use has been confirmed.

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Current scenario of pyrazole hybrids with in vivo therapeutic potential against cancers

Cited by 22 publications

References 116 publications

Design, synthesis, and anticancer evaluation of alkynylated pyrrole derivatives

Design, synthesis, and anticancer evaluation of alkynylated pyrrole derivatives

Synthesis, in vitro α‐Glucosidase Inhibition, DFT Calculations, and Molecular Docking Studies of Some New Substituted 2,5‐Bis(pyrazolyl)‐1,3,4‐oxadiazoles

Convenient One‐Pot Synthesis and Biological Evaluation of New 3,5‐Dimethyl‐1H‐pyrazole‐1‐carbothiohydrazide Derivatives as Anti‐Tumor Agents

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