Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Sharma, Pankaj; LaRosa, Chris; Antwi, Janet; Govindarajan, Rajgopal; Werbovetz, Karl A.

doi:10.3390/molecules26144213

Cited by 108 publications

(73 citation statements)

References 214 publications

(305 reference statements)

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“… 17 , 18 Progress in this attractive field was summarized in a very recent, comprehensive review. 19 Further applications of imidazolium salts of “lepidiline type” in coordination, organometallic, and materials chemistry are also possible. 18 , 19 …”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Cytotoxic Activity of Lepidilines A–D: Comparison with Some 4,5-Diphenyl Analogues and Related Imidazole-2-thiones

et al. 2021

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A straightforward access to 2-unsubstituted imidazole N -oxides with subsequent deoxygenation by treatment with Raney-nickel followed by N -benzylation opens up a convenient route to lepidilines A and C. Both imidazolium salts were used to generate in situ the corresponding imidazol-2-ylidenes, which smoothly reacted with elemental sulfur, yielding imidazole-2-thiones. These reactions were performed either under classical conditions in pyridine solutions or mechanochemically using solid Cs 2 CO 3 as a base. The structure of lepidiline C was unambiguously confirmed by X-ray analysis of its hexafluorophosphate. An analogous protocol toward lepidilines B and D and their 4,5-diphenyl analogues is less efficient due to observed instability of the key precursors, i.e., the respective 2-methylimidazole N -oxides. Comparison of cytotoxic activity against HL-60 and MCF-7 cell lines of all lepidilines, as well as their selected structural analogues (e.g., 4,5-diphenyl derivatives and PF 6 salts), revealed slightly more potent activity of the 2-methylated series, irrespectively of the type of counterion present in the imidazolium salt. Remarkably, the well-known 1,3-diadamantylimidazolium bromide (the “Arduengo salt”), known as the precursor of the first, shelf-stable NHC representative, and its adamantyloxy analogue displayed the most significant cytotoxic activity in the studied series.

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Section: Resultsmentioning

confidence: 99%

“… 19 Further applications of imidazolium salts of “lepidiline type” in coordination, organometallic, and materials chemistry are also possible. 18 , 19 …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of Lepidilines A–D: Comparison with Some 4,5-Diphenyl Analogues and Related Imidazole-2-thiones

et al. 2021

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“…The system has an amphoteric character (it can have basic or acidic properties). Imidazole is known to be present in many biologically active compounds with anticancer properties [ 224 , 225 ]. Different substituted 2-benzimidazole derivatives are active on cell lines of breast adenocarcinoma, human hepatocellular carcinoma, and human colon carcinoma [ 226 ].…”

Section: Synthetic Derivatives Of Chalcones With Anticancer Propertiesmentioning

confidence: 99%

Anticancer Activity of Natural and Synthetic Chalcones

Constantinescu

Lungu²

2021

IJMS

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Cancer is a condition caused by many mechanisms (genetic, immune, oxidation, and inflammatory). Anticancer therapy aims to destroy or stop the growth of cancer cells. Resistance to treatment is theleading cause of the inefficiency of current standard therapies. Targeted therapies are the most effective due to the low number of side effects and low resistance. Among the small molecule natural compounds, flavonoids are of particular interest for theidentification of new anticancer agents. Chalcones are precursors to all flavonoids and have many biological activities. The anticancer activity of chalcones is due to the ability of these compounds to act on many targets. Natural chalcones, such as licochalcones, xanthohumol (XN), panduretin (PA), and loncocarpine, have been extensively studied and modulated. Modification of the basic structure of chalcones in order to obtain compounds with superior cytotoxic properties has been performed by modulating the aromatic residues, replacing aromatic residues with heterocycles, and obtaining hybrid molecules. A huge number of chalcone derivatives with residues such as diaryl ether, sulfonamide, and amine have been obtained, their presence being favorable for anticancer activity. Modification of the amino group in the structure of aminochalconesis always favorable for antitumor activity. This is why hybrid molecules of chalcones with different nitrogen hetercycles in the molecule have been obtained. From these, azoles (imidazole, oxazoles, tetrazoles, thiazoles, 1,2,3-triazoles, and 1,2,4-triazoles) are of particular importance for the identification of new anticancer agents.

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“…Benzimidazole–quinolinone is another class of N -based heterocycles that has attracted a lot of interest from medicinal and synthetic organic chemists possibly due to the presence of benzimidazole and quinolinone moieties [ 58 ]. An in vitro study evaluated twenty novel benzimidazole–quinolinone derivatives against HepG2, SKOV3, NCl-H460, and BEL-7404 cancer cell lines as well as HL-7702 normal liver cell line [ 59 ].…”

Section: Heterocyclic Compoundsmentioning

confidence: 99%

Synthetic and Naturally Occurring Heterocyclic Anticancer Compounds with Multiple Biological Targets

et al. 2021

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Cancer is a complex group of diseases initiated by abnormal cell division with the potential of spreading to other parts of the body. The advancement in the discoveries of omics and bio- and cheminformatics has led to the identification of drugs inhibiting putative targets including vascular endothelial growth factor (VEGF) family receptors, fibroblast growth factors (FGF), platelet derived growth factors (PDGF), epidermal growth factor (EGF), thymidine phosphorylase (TP), and neuropeptide Y4 (NY4), amongst others. Drug resistance, systemic toxicity, and drug ineffectiveness for various cancer chemo-treatments are widespread. Due to this, efficient therapeutic agents targeting two or more of the putative targets in different cancer cells are proposed as cutting edge treatments. Heterocyclic compounds, both synthetic and natural products, have, however, contributed immensely to chemotherapeutics for treatments of various diseases, but little is known about such compounds and their multimodal anticancer properties. A compendium of heterocyclic synthetic and natural product multitarget anticancer compounds, their IC50, and biological targets of inhibition are therefore presented in this review.

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Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Cited by 108 publications

References 214 publications

Synthesis and Cytotoxic Activity of Lepidilines A–D: Comparison with Some 4,5-Diphenyl Analogues and Related Imidazole-2-thiones

Synthesis and Cytotoxic Activity of Lepidilines A–D: Comparison with Some 4,5-Diphenyl Analogues and Related Imidazole-2-thiones

Anticancer Activity of Natural and Synthetic Chalcones

Synthetic and Naturally Occurring Heterocyclic Anticancer Compounds with Multiple Biological Targets

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