Synthesis, Characterization, and Anticancer Studies of Some Pyrazole‐Based Hybrid Heteroatomics

Kuthyala, Sharanya; Sheik, Sareen; Prabhu, Ashwini; Rekha, Punchappady Devasya; Karikannar, Nagaraja Gundibasappa; Shankar, Madan Kumar

doi:10.1002/slct.202002483

Cited by 10 publications

(3 citation statements)

References 21 publications

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“…Kuthyala et al synthesized and evaluated a new series of pyrazole-based hybrid heteroaromatics for their in vitro antiproliferative activity against A549 lung cancer cells [ 56 ]. Among the derivatives, compounds 31 and 32 exhibited the most potent activity, with IC 50 values of 42.79 and 55.73 μM, respectively against the A549 cells.…”

Section: Kinase Inhibitorsmentioning

confidence: 99%

Recent Advances in the Development of Pyrazole Derivatives as Anticancer Agents

Zhang

et al. 2023

IJMS

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Pyrazole derivatives, as a class of heterocyclic compounds, possess unique chemical structures that confer them with a broad spectrum of pharmacological activities. They have been extensively explored for designing potent and selective anticancer agents. In recent years, numerous pyrazole derivatives have been synthesized and evaluated for their anticancer potential against various cancer cell lines. Structure–activity relationship studies have shown that appropriate substitution on different positions of the pyrazole ring can significantly enhance anticancer efficacy and tumor selectivity. It is noteworthy that many pyrazole derivatives have demonstrated multiple mechanisms of anticancer action by interacting with various targets including tubulin, EGFR, CDK, BTK, and DNA. Therefore, this review summarizes the current understanding on the structural features of pyrazole derivatives and their structure-activity relationships with different targets, aiming to facilitate the development of potential pyrazole-based anticancer drugs. We focus on the latest research advances in anticancer activities of pyrazole compounds reported from 2018 to present.

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Section: Kinase Inhibitorsmentioning

confidence: 99%

Recent Advances in the Development of Pyrazole Derivatives as Anticancer Agents

Zhang

et al. 2023

IJMS

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“…[4] Because of these facts, hybrids of pyrazole, thiophene, and 1,2,3-triazole are the main focus of this investigation because these heterocycles exhibit a variety of pharmacological activities. In various works of literature, the pyrazole nucleus has demonstrated a variety of biological activities such as antimicrobial, [1,2,[5][6][7][8][9] antitubercular, antibiofilm, [5] antimalarial, [6] anticancer, [7][8][9][10][11][12] antioxidant, [11][12][13] anti-inflammatory and analgesic [14] activities. According to the currently reported literature, the pyrazole ring exhibited activity in antioxidant, pancreatic lipase, and GABA-AT inhibitory functions, with excellent molecular docking and ADMET profiles.…”

Section: Introductionmentioning

confidence: 99%

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Sherashiya,

Kanjariya,

Naliapara

et al. 2024

ChemistrySelect

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To achieve environmentally benign synthesis and develop pharmacologically active compounds, a library of novel thiophene‐clubbed pyrazole‐1,2,3‐triazole hybrids was designed and successfully synthesized using L‐ascorbic acid as a green acid catalyst and ethanol as a green solvent. The reaction was carried out using microwave and ultrasonic irradiation methods to achieve a highly efficient reaction route. All title compounds were characterized and evaluated for their potential in vitro antimicrobial activity using Ciprofloxacin and Nystatin as standard drugs, in which compounds with chloro and naphthyl substitutions exhibited excellent antibacterial activity at concentrations of 25 μg/mL and compounds with methyl and methoxy substitutions exhibited excellent antifungal activity at concentrations of 100 μg/mL. Additionally, the molecular docking study showed that all compounds examined had excellent binding energies ranging from −9.3 to −10.3 kcal/mol, and naphthyl substitution displayed the highest binding energy (−10.3 kcal/mol) on the target protein of E. coli DNA gyrase subunit B. Furthermore, the final moieties were evaluated for in silico ADMET prediction to examine their drug‐likeness profile and toxic effects. The present study revealed that this structural information will be helpful in future antimicrobial drug design and development.

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“…Furthermore, hybridization of ethyl 1-phenyl-1 H -benzo[ d ]imidazole-2-carboxylate with alicyclic amines yielded benzo[ d ]imidazole-2-carboxamides as anti-TB agents and others. − The presence of two or more biologically active pharmacophores within a single unit not only synergizes the biological activity but also enhances the ability to interact with more than one biological target . Moreover, the pyrazole ring system also has a wide range of biological activities, including antifungal, antimicrobial, anticancer, − anti-AIDS, and antidepressants . The pyrazole ring system is an important bioactive ingredient in over-the-counter drugs such as pyrazomycin (anticancer drug), floxan (anti-inflammatory drug), and difenamizole (nonsteroidal anti-inflammatory drug) (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Novel Thiopyrano[2,3-d]thiazole-pyrazole Hybrids as Potential Nonsulfonamide Human Carbonic Anhydrase IX and XII Inhibitors: Design, Synthesis, and Biochemical Studies

Metwally

El-Desoky

2023

ACS Omega

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In recent years, molecular hybridization strategies have developed into a potent strategy for drug discovery. A series of novel thiopyrano [2,3-d]thiazoles linked to the pyrazole moiety was designed and developed as anticancer agents by a molecular hybridization. Target compounds were synthesized and characterized by spectroscopic tools as well as X-ray crystallography analysis as in the case of thiopyrano[2,3d]thiazole derivative 5a. The MTT assay was used to demonstrate the in vitro efficacy of compounds 5a−g and 7a−j on MCF-7 and HePG-2. The results showed that some cycloadducts such as bromophenyl-4-thioxo-2-thiazolidinone 3e, 4-methylphenyl derivative of thiopyrano[2,3-d]thiazole 5d, and 6substituted-thiopyrano[2,3-d]thiazoles 7e−j displayed good to excellent IC 50 in the range of 10.08 ± 1.5 to 25.95 ± 2.8 μg/mL against the MCF-7 cell line and from 7.83 ±2.1 to 13.37 ± 1.2 μg/mL against the HePG-2 cell line. To explore the enzymatic tests for isozymes hCAIX and hCAXII, the most promising eight compounds 3e, 5d, and 7e−j with IC 50 ranging from 7.83 ± 2.1 to 25.95 ± 2.8 μM were chosen. Compound 7e exhibited an IC 50 (0.067 ± 0.003 μM) similar to that of the standard drug AZA against CAIX (0.059 ± 0.003 μM)). For CAXII, the compound 7i had an IC 50 equal to 0.123 ± 0.007 μM compared to that of AZA (0.083 ± 0.005 μM). In addition, using flow cytometry, cell cycle analysis and apoptosis studies in HePG-2 were performed for the two potent anticancer and selective carbonic anhydrase agents (7e and 7i). An enzymatic assay of these two compounds against caspase-9 was also examined. Interestingly, the molecular docking studies revealed that compounds 7e and 7i successfully embedded themselves in the active pockets of the CAIX and CAXII enzymes through different interactions. Overall, the novel thiopyrano[2,3-d]thiazole-pyrazole hybrids (7e and 7i) were suggested to be potent and selective inhibitors of CAIX and CAXII.

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Synthesis, Characterization, and Anticancer Studies of Some Pyrazole‐Based Hybrid Heteroatomics

Cited by 10 publications

References 21 publications

Recent Advances in the Development of Pyrazole Derivatives as Anticancer Agents

Recent Advances in the Development of Pyrazole Derivatives as Anticancer Agents

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Novel Thiopyrano[2,3-d]thiazole-pyrazole Hybrids as Potential Nonsulfonamide Human Carbonic Anhydrase IX and XII Inhibitors: Design, Synthesis, and Biochemical Studies

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