Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin

Raghavan, Saiharish; Manogaran, Prasath; Kuppuswami, Balasubramanian Kalpattu; Venkatraman, Ganesh; Narasimha, Krishna Kumari Gadepalli

doi:10.1007/s00044-015-1453-2

Cited by 26 publications

(11 citation statements)

References 23 publications

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“…In other cases, the products were purified by using silica gel chromatography. Compounds 1 – 7 , 9 – 10 , 13 , 14 , 16 , 19 – 20 , 22 , 24 , 26 , 28, 32, 36 , 38 and 40 were published previously in the literature74., 75., 76., 77., 78., 79., 80., 81., 82., 83., 84., 85., 86., 87., 88., 89., and their spectral data are in the Supporting Information. The spectral data of novel or unreported compounds are listed as follows.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis and biological evaluation of chalcone analogues with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents

Wang

Huang

Cheng

et al. 2019

Acta Pharmaceutica Sinica B

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Scavenging reactive oxygen species (ROS) by antioxidants is the important therapy to cerebral ischemia-reperfusion injury (CIRI) in stroke. The antioxidant with novel dual-antioxidant mechanism of directly scavenging ROS and indirectly through antioxidant pathway activation may be a promising CIRI therapeutic strategy. In our study, a series of chalcone analogues were designed and synthesized, and multiple potential chalcone analogues with dual antioxidant mechanisms were screened. Among these compounds, the most active 33 not only conferred cytoprotection of H 2 O 2 -induced oxidative damage in PC12 cells through scavenging free radicals directly and activating NRF2/ARE antioxidant pathway at the same time, but also played an important role against ischemia/reperfusion-related brain injury in animals. More importantly, in comparison with mono-antioxidant mechanism compounds, 33 exhibited higher cytoprotective and neuroprotective potential in vitro and in vivo. Overall, our findings showed compound 33 could emerge as a promising anti-ischemic stroke drug candidate and provided novel dual-antioxidant mechanism strategies and concepts for oxidative stress-related diseases treatment.

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Section: Methodsmentioning

confidence: 99%

Design, synthesis and biological evaluation of chalcone analogues with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents

Wang

Huang

Cheng

et al. 2019

Acta Pharmaceutica Sinica B

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“…Novel chalcones and indole derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were synthesized and tested against the bacteria strains Staphylococcus aureus, E. coli and Bacillus sphaericus with reference to the standard drug Ciprofloxacin at the concentration 1 µg/mL. Again synthesized compounds were tested against the fungal strains Apergillus niger, Penicillium funiculosum and Fusarium oxysporum with reference to the standard ketoconazole at the Stock solution: 1 mg/mL (DMSO) A = 40 µL, B = 80 µL concentration 1 µg/mL.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activities of Chalcones and Indole Derived from Acetyl Pyridines

Santra¹,

Jat²,

Santra³

2018

Asian J. Chem.

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Chalcones due to its diverse biological and pharmacological activities have generated extensive scientific studies throughout the world. Chalcones having substitution on two aryl rings exhibit anticancer, antioxidant, anti-inflammatory, antimicrobial, antiulcer, antimalaria and many other activities [1-9]. Chalcones and their derivatives have also been seen to find applications in large varieties of diverse areas such as artificial sweeteners [10], scintillator [11], stabilizer against heat, visible light, ultraviolet light and aging [12,13]. In agriculture, chalcones are used to destroy phytopathogenic organisms [14]. Similarly in industry chalcones are also used in anti-sunburn oil [15]. Indole nucleus is a biologically accepted pharmacophore in medicinal compounds. Compounds bearing indole nucleus exhibit wide spectrum of biological activities such as antifungal, antimicrobial, antiviral, antitubercular, anticancer etc. [16,17]. In the present study, it was thus been decided to synthesize and characterize chalcones and indole bearing nitrogen containing heterocyclic ring such as pyridine ring with substitutions selected from-F,-NO2,-NH2 and to screen the antibacterial and antifungal activity of the synthesized compounds.

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“…A series of chalcone derivatives consist of 48 compounds along with their cytotoxic activity against MCF7 cells from the research of Suma et al, 2019;Syam et al, 2012;Raghavan et al, 2015;Ivkovic et al, 2013;and Shenvi et al, 2013 were used for the QSAR analysis. The proposed compound obtained from QSAR analysis and the crystal structure of the Cyclooxygenase-2 enzyme with PDB ID: 4COX and 6COX were used for molecular docking.…”

Section: Methodsmentioning

confidence: 99%

“…A total of 48 chalcone derivatives (Table 1) were selected from the recently published literature, i.e., Suma et al, 2019;Syam et al, 2012;Raghavan et al, 2015;Ivkovic et al, 2013;and Shenvi et al, 2013. All of their activities towards MCF7 cell lines have been reported using the same biological assay method.…”

Section: Data Set Preparationmentioning

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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Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin

Cited by 26 publications

References 23 publications

Design, synthesis and biological evaluation of chalcone analogues with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents

Design, synthesis and biological evaluation of chalcone analogues with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents

Synthesis and Antimicrobial Activities of Chalcones and Indole Derived from Acetyl Pyridines

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

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