Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole tethered chalcone hybrids as potential anticancer agents

Gurrapu, Nirmala; Kumar, E. Praveen; Kolluri, Prashanth Kumar; Putta, Shravani; Sivan, Sree Kanth; Subhashini, N

doi:10.1016/j.molstruc.2020.128356

Cited by 37 publications

(26 citation statements)

References 19 publications

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“…Gurrapu et al. 61 also synthesised novel 1,2,3-triazole chalcone hybrids as potential anticancer agents. All of these compounds were effective ; however, meta methyl substituent attached to the triazole ring meta, para dimethoxy substituted attached to the chalcone ring of compounds 9a ( Figure 4 ), meta chloro substitutes attached to the triazole ring and meta, para dimethoxy substituted attached to the chalcone ring of compound 9b ( Figure 4 ), and meta chloro substituent attached to the triazole ring and meta hydroxy substituted attached to the chalcone ring of compound 9c ( Figure 4 ) were nearly equipotent and exhibited increased efficiently against cancer cell lines.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Derivatives of chalcones-triazole not only exert anti-breast cancer activity 60 , 61 , but also they exhibit activity against multiple types of cancer cells 101 , 102 . A new series of 1,2,3-triazole-chalcone hybrids was synthesised by Ashour and et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Chalcone-triazole derivatives not only possess anticancer activity 60 , 61 , 101 , 102 , but also they exhibit anti-inflammatory activity 114 . Boshra et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Chalcone-triazole derivatives not only possess anticancer activity 60 , 61 , 101 , 102 , anti-inflammatory activity 114 , antibacterial activity 125–127 , and antibacterial activity 134 , but also they exhibit antimalarial activity 143 , 144 . Kant et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

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Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Nature products have been extensively used in the discovery and development of new drugs, as the most important source of drugs. The triazole ring is one of main pharmacophore of the nitrogen-containing heterocycles. Thus, a new class of triazole-containing natural product conjugates has been synthesised. These compounds reportedly exert anticancer, anti-inflammatory, antimicrobial, antiparasitic, antiviral, antioxidant, anti-Alzheimer, and enzyme inhibitory effects. This review summarises the research progress of triazole-containing natural product derivatives involved in medicinal chemistry in the past six years. This review provides insights and perspectives that will help scientists in the fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology.

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Section: Biological Activitiesmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

“…Chalcone-triazole derivatives not only possess anticancer activity 60 , 61 , 101 , 102 , but also they exhibit anti-inflammatory activity 114 . Boshra et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

See 2 more Smart Citations

Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The QSAR of chalcones with an anticancer activity has been done with HT-29 human colon adenocarcinoma cell lines (Rybka et al, 2014). Meanwhile, molecular docking of chalcone derivatives that have been done was against cyclin-dependent kinase CDK7 (Khanapure et al, 2018), α-β tubulin (Pingaew et al, 2014), α-estrogen receptors (Gurrapu et al, 2020), and EGFR (Suma et al, 2019). The combination of QSAR analysis with molecular docking for designing the chalcone derivatives as anticancer towards MCF7 cancer cell lines had not been reported.…”

Section: Introductionmentioning

confidence: 99%

Design of New Chlorochalcone Derivatives as Potential Breast Anticancer Compound Based on QSAR Analysis and Molecular Docking Study

Puspitasari

Pranowo

Astuti

et al. 2021

CMUJNS

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Quantitative structure-activity relationships (QSAR) proposes a model that relates the biological activities of drugs to their chemical structures, and the interaction between the drug and its target enzyme is revealed by molecular docking research. These studies were conducted on chalcone to produce a model that could design highly potent breast anticancer MCF7 cells. The compounds were optimized using ab initio using a basis set 6-31G, then their descriptors calculated using this method. Genetic Function Algorithm (GFA) was used to select descriptors and build the model. One of the six models generated was found to be the best with internal and external squared correlation coefficient (R2) of 0.743 and 0.744, respectively, adjusted squared correlation coefficient (adjusted R2) of 0.700, Standard estimate of error (SEE) of 0.198, Fcalc/Ftable of 6.423, and Predicted residual sum of squares (PRESS) of 1.177. The QSAR equation is pIC50 = 3.869 + (1.427 x qC1) + (4. 027 x qC10) + (0.856 x qC15) - (35.900 x ELUMO) + (0.208 x Log P). Hence, it can predict the breast anticancer activities of new chlorochalcones A-F. The compound with the best prediction was chlorochalcone A with pIC50 2.65 and IC50 value of 2.26 μM. The chlorochalcones A-F were able to bind to the main amino acid residues, namely Arg120 and Tyr355, on the active site of the COX-2 enzyme. These results could serve as a model for designing novel chlorochalcone as inhibitors of COX-2 with higher breast anticancer activities. Keywords: Chlorochalcone, COX-2, QSAR, MCF-7, Molecular docking

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Current scenario of chalcone hybrids with antibreast cancer therapeutic applications

Wang,

Zhu,

Zhang

et al. 2024

Archiv der Pharmazie

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Breast cancer, an epithelial malignant tumor that occurs in the terminal ducts of the breast, is the most common female malignancy. Currently, approximately 70%–80% of breast cancer with early‐stage, nonmetastatic disorder is curable, but the emergency of drug resistance often leads to treatment failure. Moreover, advanced breast cancer with distant organ metastases is incurable with the available therapeutics, creating an urgent demand to explore novel antibreast cancer agents. Chalcones, the precursors for flavonoids and isoflavonoids, exhibit promising activity against various breast cancer hallmarks, inclusive of proliferation, angiogenesis, invasion, metastasis, inflammation, stemness, and regulation of cancer epigenetics, representing useful scaffolds for the discovery of novel antibreast cancer chemotherapeutic candidates. In particular, chalcone hybrids could act on two or more different biological targets simultaneously with more efficacy, lower toxicity, and less susceptibility to resistance. Accordingly, there is a huge scope for application of chalcone hybrids to tackle the present difficulties in breast cancer therapy. This review outlines the chalcone hybrids with antibreast cancer potential developed from 2018. The structure–activity relationships as well as mechanisms of action are also discussed to shed light on the development of more effective and multitargeted chalcone candidates.

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Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole tethered chalcone hybrids as potential anticancer agents

Cited by 37 publications

References 19 publications

Application of triazoles in the structural modification of natural products

Application of triazoles in the structural modification of natural products

Design of New Chlorochalcone Derivatives as Potential Breast Anticancer Compound Based on QSAR Analysis and Molecular Docking Study

Current scenario of chalcone hybrids with antibreast cancer therapeutic applications

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