Synthesis and bioevaluation of diarylpyrazoles as antiproliferative agents

Wang, Chao; Yang, Shuang; Du, Jianan; Ni, Jincheng; Wu, Yue; Wang, Junfang; Guan, Qı; Zuo, Daiying; Bao, Kai; Wu, Yingliang; Zhang, Weige

doi:10.1016/j.ejmech.2019.02.049

Cited by 18 publications

(12 citation statements)

References 31 publications

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“…Pyrazole is an important bioactive heterocycle [29][30][31] possessing anti-inflammatory, antimalarial, anticancer, antipyretic, antitubercular, antidepressant, antiobesity, anticonvulsant, antihyperglycemic, antioxidant properties and is gaining significant importance in the pharmaceuticals. [32][33][34][35][36] Pyrazole derivatives show anticancer activity known to their inhibition of various targets such as mammalian target of rapamycin (mTOR), epidermal growth factor receptor (EGFR), phosphoinositide 3-kinases (PI3 K), topoisomerase II, vascular endothelial growth factor (VEGF), insulin-like growth factor type 1 receptor (IGF-1R), Histone deacetylase (HDAC), Proto-oncogene tyrosineprotein kinase (ROS1), mesenchymal-epithelial transition factor (cMet), anaplastic lymphoma kinase (ALK), thus providing excellent results especially against human liver cancer cell line (HepG-2), Michigan Cancer Foundation-7 breast cancer cell line (MCF-7), adenocarcinomic human alveolar basal epithelial cell lines (A-549), and Henrietta Lacks immortal cell lines (HeLa). [37] Recently there are numerous reviews on the biological significance of pyrazole derivatives.…”

Section: Pyrazoles As Cox-2 Inhibitorsmentioning

confidence: 99%

Structural Insights into Pyrazoles as Agents against Anti‐inflammatory and Related Disorders

et al. 2022

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Pyrazole moiety is considered as the most important therapeutic agent for the treatment of inflammation and inflammation associated cancers. Celecoxib, Ramifenazone, Rimonabant and Lonazolac are some of the commercially available pyrazole moieties which are potent COX‐2 inhibitors and also acts in inhibiting various cancers. Recently there are numerous reviews on the biological significance of pyrazole derivatives. However, this review discusses pyrazole derivatives possessing anti‐inflammatory and anticancer activity (COX inhibition) and also illustrates the recent updates on pyrazole research emphasizing on the medicinal chemistry aspects such as the key structural fragments required for the biological activity. There are series of pyrazoles like di‐substituted, tri‐substituted, tetra‐substituted pyrazoles, pyrazole hydrazones, pyrazoles bearing various other heterocycles, bicyclic fused pyrazoles, tricyclic fused pyrazoles, and miscellaneous class of pyrazoles. All these pyrazoles are being researched as COX inhibitors, anti‐inflammatory and against related disorders like cancer.

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Section: Pyrazoles As Cox-2 Inhibitorsmentioning

confidence: 99%

Structural Insights into Pyrazoles as Agents against Anti‐inflammatory and Related Disorders

et al. 2022

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“…[ 8,14 ] In addition, pyrazoles and isoxazoles are important heterocyclic scaffolds due to their wide variety of pharmacological activities. Pyrazole derivatives have several potential applications such as anti‐HIV, [ 15 ] antimicrobial, [ 16,17 ] antiproliferative, [ 18 ] antioxidant, [ 19 ] antibacterial, [ 20 ] antifungal, [ 21 ] anti‐inflammatory, [ 20 ] anticancer, [ 22,23 ] antimalarial, [ 24 ] antifibrosis, [ 25 ] and so forth. Further, pyrazole derivatives have also been reported by our group to have potential as CAIs ( 1 – 7 ), [ 26–28 ] besides being associated with a diverse range of biological activities (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Novel benzenesulfonamide‐bearing pyrazoles and 1,2,4‐thiadiazoles as selective carbonic anhydrase inhibitors

Kumar

Ram

et al. 2021

Archiv der Pharmazie

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Two series comprising 20 novel benzenesulfonamides bearing thioureido‐linked pyrazole 8 and amino‐1,2,4‐thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor‐associated isoforms IX and XII. Molecular modeling studies of some potent derivatives (8a, 8c, 10a, and 10c) were also performed against isoforms hCA I, II, and XII. Both the promising series of compounds were synthesized by using commercially available mtethyl ketones and sulfanilamide as the starting materials. Interestingly, this paper also reports a novel methodology for the synthesis of amino‐1,2,4‐thiadiazoles 10 using 3‐amino isoxazoles and 4‐isothiocyanatobenzenesulfonamide as reactants. The activity profile of all the newly synthesized compounds reveals that amino‐linked 1,2,4‐thiadiazoles 10 were better inhibitors of the cytosolic isoform, hCA I, as compared to thioureido‐linked pyrazoles 8. Further, hCA II was strongly inhibited by nearly all the newly synthesized sulfonamides, while all the compounds were less effective as hCA IX and XII inhibitors compared to the standard drug acetazolamide. However, in terms of selectivity, compound 8e was found to be the most selective inhibitor of hCA II, which is the isoform associated with glaucoma, edema, altitude sickness, and epilepsy.

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“…Traditional strategies for constructing polysubstituted pyrazoles are annulations initiated by the condensation of hydrazine compounds with carbonyl derivatives (Scheme a), − or 1,3-dipolar cycloadditions of diazo molecules with alkenes or alkynes (Scheme b). − For example, chloramine-T was commonly used to generate 1,3-dipolar species and subsequent 1,3-dipolar cycloadditions for the synthesis of pyrazoles would smoothly occur. All these reactions were mainly focused on bisarylhydrazones in the presence of excessive chloramine-T.…”

Section: Introductionmentioning

confidence: 99%

Iodine-Catalyzed Regioselective Oxidative Cyclization of Aldehyde Hydrazones with Electron-Deficient Olefins for the Synthesis of Mefenpyr-Diethyl

et al. 2019

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A regioselective synthesis of polysubstituted dihydropyrazoles and pyrazoles through an iodine-catalyzed oxidative cyclization strategy of aldehyde hydrazones with electron-deficient olefins is described. The protocol adopts very mild reaction conditions and provides desirable yields. The reaction is supposed to proceed via a cascade C–H functionalization, C–N bond formation, and oxidation sequential processes. The overall simplicity and regioselectivity of the catalytic system make this approach a valuable and step-economical tool to construct a C–C bond for the synthesis of Mefenpyr-Diethyl.

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Synthesis and bioevaluation of diarylpyrazoles as antiproliferative agents

Cited by 18 publications

References 31 publications

Structural Insights into Pyrazoles as Agents against Anti‐inflammatory and Related Disorders

Structural Insights into Pyrazoles as Agents against Anti‐inflammatory and Related Disorders

Novel benzenesulfonamide‐bearing pyrazoles and 1,2,4‐thiadiazoles as selective carbonic anhydrase inhibitors

Iodine-Catalyzed Regioselective Oxidative Cyclization of Aldehyde Hydrazones with Electron-Deficient Olefins for the Synthesis of Mefenpyr-Diethyl

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