New ferrocenyl-chalcones and bichalcones: Synthesis and characterization

Trujillo, Alexander; Ocayo, Fernanda; Artigas, Vania; Santos, Juan C.; Jara‐Ulloa, Paola; Kahlal, Samia; Saillard, Jean Yves; Fuentealba, Mauricio; Escobar, Carlos A.

doi:10.1016/j.tetlet.2016.12.046

Cited by 13 publications

(4 citation statements)

References 27 publications

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“…These electronic transitions offer a promising application as the sunscreen agent as chalcone derivatives can absorb the UV light before reaching the human skin. Furthermore, sunscreen agent based on chalcone derivatives is possible to develop for large-scale commercial production as chalcones can be easily synthesized by reacting benzaldehyde and acetophenone derivatives through a Claisen-Schmidt condensation reaction under the alkaline condition as shown in Scheme 1 [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

et al. 2021

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Ultraviolet (UV) irradiation is a serious problem for skin health thus the interest in the research to develop sunscreen agent has been increasing. Chalcone is a promising compound to be developed as its chromophore absorbs in the UV region. Therefore, in the present work, we synthesized eight chalcone derivatives through Claisen–Schmidt condensation at room temperature. The evaluation of the optical properties of each chalcone derivatives in the UV region was conducted through spectroscopic and computational studies. The synthesized chalcones were obtained in good yields and they were active in the UV region. The results revealed that more methoxy substituents to chalcone leads toward red shift. All chalcone derivatives have high molar absorptivity value (21,000–56,000) demonstrating that they have the potential to be used as the sunscreen agent. The cytotoxicity assay showed that chalcone derivatives were demonstrating low toxicity toward normal human fibroblast cell, which is remarkable. Therefore, we concluded that the synthesized chalcones in this work were potential to be developed as novel sunscreen agents in real application.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

et al. 2021

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“…Licochalcone from the licorice root in China has been reported to be a promising antimalarial agent. Synthesis of ferrocenyl chalcones was obtained by replacing the aromatic ring with a ferrocenyl moiety [50,51,52,53]. Researchers synthesized several ferrocenyl chalcone derivatives by base-catalyzed Claisen–Schmidt condensation.…”

Section: Ferrocene-based Compounds With Antimalaria Activitymentioning

confidence: 99%

Ferrocene-Based Compounds with Antimalaria/Anticancer Activity

2019

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Malaria and cancer are chronic diseases. The challenge with drugs available for the treatment of these diseases is drug toxicity and resistance. Ferrocene is a potent organometallic which have been hybridized with other compounds resulting in compounds with enhanced biological activity such as antimalarial and anticancer. Drugs such as ferroquine were developed from ferrocene and chloroquine. It was tested in the 1990s as an antimalarial and is still an effective antimalarial. Many researchers have reported ferrocene compounds as potent compounds useful as anticancer and antimalarial agents when hybridized with other pharmaceutical scaffolds. This review will be focused on compounds with ferrocene moieties that exhibit either an anticancer or antimalarial activity.

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“…In this context, following the search for new ferrocene containing materials [11], we are describing here the synthesis and characterization of five new star-like compounds bearing ferrocenyl endgroups featuring isocyanurate and 1,3,5-phenylene cores. The main objective of this work is to evaluate the electron conjugation effect across the central cores bearing two kinds of branches: the vinyl ferrocenyl and the cross-conjugated ferrocenyl-chalcone, on the electrochemical potentials of the Fc/Fc + couple and on the changes produced on lowest energy transition of electronic absorption spectra.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new star-like triply ferrocenylated compounds

Santos¹,

Madrid-Moliné²,

Cisternas³

et al. 2019

Inorganica Chimica Acta

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New ferrocenyl-subtituted compounds containing two different central cores (isocyanurate and 1,3,5-phenylene) and extended by two kinds of branches bearing both vinyl ferrocenyl (1 and 3) and cross-conjugated ferrocenyl-chalcone (2, 4 and 5) as endgroups have been synthetized and characterized both spectroscopically and electrochemically. These molecules have been synthesized in order to investigate the electronic properties imparted by both types of branches when they are connected to the central core. For all compounds, electrochemical studies have showed a simultaneous oxidation of all ferrocene units present in each compound. For all of them, except for compound 2, a chemically reversible oxidation wave on the voltammograms has been observed. In contrast, for compound 2, a chemically irreversible oxidation wave is obtained. Moreover, the vinyl ferrocenyl derivatives have presented a lower redox peak potential with respect to ferrocene standard compound, and the ferrocenyl-chalcone bearing derivatives, in accordance with a change in the electron releasing capability of these endgroups, have been oxidized at a higher potential. Bathochromic shifts of the active transitions in Uv-Vis region have been observed, which are associated to the presence of carbonyl groups in those molecular structures containing it. These results are in agreement with theoretically calculated transition energies, which have been obtained for compounds 1 and 2 using Time Dependent Density Functional Theory (TD-DFT).

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New ferrocenyl-chalcones and bichalcones: Synthesis and characterization

Cited by 13 publications

References 27 publications

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

Ferrocene-Based Compounds with Antimalaria/Anticancer Activity

Synthesis of new star-like triply ferrocenylated compounds

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