Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models

Mellado, Marco; Madrid, Alejandro; Reyna, Mauricio; Weinstein‐Oppenheimer, Caroline; Mella, Jaime; Salas, Cristian O.; Sánchez, Elizabeth; Cuéllar, Mauricio

doi:10.1007/s00044-018-2245-2

Cited by 31 publications

(28 citation statements)

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“…The term chalcone is used to name compounds characterized by the presence of 1,3-diphenyl-2-propen-1-one subunit [21]. Chalcones and their derivatives exhibit many activities (anticancer, anti-inflammatory, antioxidant, cytotoxic, antibacterial, analgesic, antipyretic, antihepatotoxic, antimalarial, and anti-allergic) [22,23,24]. Chalcones play the role of pharmacophore in many natural products such as cumarin, flavokawain, milepachin, and xanthohumol [25].…”

Section: Introductionmentioning

confidence: 99%

Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

2019

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Lipophilcity is an important physico-chemical parameter that influences membrane transport and binding ability to action. Migration distance following complete elution of compounds was used to calculate different lipophilicity-related parameters. The aim of this study is to show that lipophilicity is a central component of thiazole chalcones and flavonoid derivatives regarding their drug-like properties. Experimental and computational methods were used. This study considers 44 previously synthesized compounds (thiazole chalcones, flavanones, flavones, 3-hydroxyflavones, and their acetylated derivatives). The concerned compounds have shown antitumoral hallmarks and antibacterial activity in vitro. The experimental method used to determine compounds’ lipophilicity was the reverse-phase thin layer chromatography (RP-TLC). Lipophilicity related parameters—isocratic retention factor (RM), relative lipophily (RM0), slope (b), chromatographic hydrophobic index (φ0), scores of principal components (PC1/RM)—were determined based on reverse-phase chromatography results.

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Section: Introductionmentioning

confidence: 99%

Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

2019

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“…To this end, quantitative structure–activity relationship (QSAR) analysis (i.e., a series of multivariate linear regressions between biological activity (pEC 50 , dependent variable) and various descriptors (physicochemical, steric, or other, independent variables)) was performed following [ 28 , 29 , 30 ], in order to better describe activity and aid in the design and prediction of new compounds [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

Sonochemical Synthesis of 2’-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity

López

Mellado

Werner³

et al. 2020

Antibiotics

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This work reports on the synthesis of eight new 2′-hydroxy-chalcones with potential anti-phytopathogenic applications in agroindustry, among others, via Claisen–Schmidt condensation and ultrasound assisted reaction. Assays showed three chalcones with allyl moieties strongly inhibited growth of phytopathogenic oomycete Phytophthora infestans; moreover, compound 8a had a half maximal effective concentration (EC50) value (32.5 µg/mL) similar to that of metalaxyl (28.6 µg/mL). A software-aided quantitative structure–activity relationship (QSAR) analysis of the whole series suggests that the structural features of these new chalcones—namely, the fluoride, hydroxyl, and amine groups over the carbon 3′ of the chalcone skeleton—increase anti-oomycete activity.

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“…The structure was determined by NMR experiments ( 1 H, 13 C, 2D‐HSQC, and 2D‐HMBC, data not showed), and compared with previous reports . To obtain the desired prenylated chalcones ( 7 a‐g ), the acetophenone 5 was condensed by Claisen‐Schmidt reaction with differently substituted benzaldehydes ( 6 a‐g ), using alkaline media (Scheme ), according to the previously reported data from the research group, with yields from 14 to 92% …”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Docking Calculations of Prenylated Chalcones as Selective Monoamine Oxidase B Inhibitors with Antioxidant Activity

et al. 2019

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Different natural and synthetic chalcones have exhibited selective inhibition on monoamine oxidase B (MAOÀ B) activity, demonstrating potential interest for the treatment of neurodegenerative diseases. Herein we report the synthesis of seven new prenylated chalcones (7a-g) obtained from the natural compound 5 (4-hydroxy-3-(3-methylbut-2-en-1-yl)phenylethanone), previously isolated from S. graveolens. Five of these compounds exhibit high inhibition and selectivity against MAOÀ B, with IC 50 values in the low micromolar range. In addition, the antioxidant activity of this series was measured, being three compounds better than the reference, butylated hydroxytoluene (BHT). Compound 7 f [(2E)-3-(4-(dimethylamino) phenyl)-1-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)prop-2en-1-one] proved to be the best compound within the studied series (IC 50 MAO-B = 8.19 μM and k DPPH = 3.73). Finally, molecular docking was performed to better understand the binding properties of these derivatives. Important features for MAOÀ B inhibitory activity were observed: hydrogen-bonding interaction between Tyr435 and nearness with Tyr398 and FAD co-factor. Therefore, these molecules are good candidates for the design of a lead compound for Parkinson's disease.

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Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models

Cited by 31 publications

References 53 publications

Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

Sonochemical Synthesis of 2’-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity

Design, Synthesis and Docking Calculations of Prenylated Chalcones as Selective Monoamine Oxidase B Inhibitors with Antioxidant Activity

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