Synthesis of cinnamic acid ester derivatives with antiproliferative and antimetastatic activities on murine melanoma cells

Vale, Juliana A.; Rodrigues, Michelle Peixoto; Lima, Ângela Maria Almeida; Santiago, Samira Soares; Lima, Graziela Domingues de Almeida; Almeida, Alisson Andrade; Oliveira, Leandro Licursi de; Bressan, Gustavo Costa; Teixeira, Róbson Ricardo; Machado‐Neves, Mariana

doi:10.1016/j.biopha.2022.112689

Cited by 20 publications

(26 citation statements)

References 63 publications

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“…It was found that trans-cinnamic acid compounds have non-toxic properties in contrast to the used positive control Ellipticine. This cinnamoyl moiety was also observed in various types of biologically active substances and has been used to build new active compounds for anticancer [12][13], antiproliferative [14], anti-inflammatory [15] and antimicrobial [16] agents. Through maintaining the cinnamate structure, the molecular hybridization approach can be used by combining this compound with other active compounds to design a more active anticancer agent [17].…”

Section: ■ Introductionmentioning

confidence: 94%

Synthesis, Cytotoxicity Evaluation and Molecular Docking Studies of Xanthyl-Cinnamate Derivatives as Potential Anticancer Agents

Iresha

Jumina²,

Pranowo³

et al. 2022

Indones. J. Chem.

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A new series of xanthyl-cinnamate hybrid compounds (4a-d) have been synthesized and screened through in vitro assay against four human cancer cell lines, i.e., HeLa, T47D, A549, and WiDr. The results revealed that xanthone hybridization with cinnamic acid increases the selectivity of the compounds with SI values of 2.75–209.03 compared to its parent oxygenated-xanthone. Compound 1,3-dihydroxyxanthen-6-yl cinnamate (4c) showed high cytotoxic activity against WiDr cell lines with an IC50 value of 39.57 µM. Molecular docking studies revealed the possible binding modes of all hybrid compounds with EGFR protein. A complex of 3,6-dihydroxyxanthen-1-yl cinnamate (4d)-EGFR, as the best binding model, exhibited higher predicted EGFR inhibitory activity than erlotinib and oxygenated-xanthone with a ΔG and Ki value of -35.02 kJ/mol and 0.74 µM, respectively. Compounds 4c and 4d were chosen as the most potent derivates from the study.

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Section: ■ Introductionmentioning

confidence: 94%

Synthesis, Cytotoxicity Evaluation and Molecular Docking Studies of Xanthyl-Cinnamate Derivatives as Potential Anticancer Agents

Iresha

Jumina²,

Pranowo³

et al. 2022

Indones. J. Chem.

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“…Vale et al obtained new cinnamic acid ester derivatives [ 113 ]. The basis for the syntheses was the confirmed anticancer activity of cinnamic acid and its derivatives against melanoma [ 110 , 111 , 112 ].…”

Section: The Most Potent Anti-melanoma Agent From Most Recent Studies...mentioning

confidence: 99%

“…Biological studies also indicated that (44) disturbed cell invasion, adhesion, colonization, and polymerization of actin. The high activity of the proposed compound is probably related to the addition of two bromine atoms to the double bond of the cinnamic acid structure, which had a favorable effect on bioavailability and interaction with the biological target [ 113 ].…”

Section: The Most Potent Anti-melanoma Agent From Most Recent Studies...mentioning

confidence: 99%

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

Kozyra

Krasowska

Pitucha

2022

IJMS

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Malignant melanoma (MM) is the most lethal skin cancer. Despite a 4% reduction in mortality over the past few years, an increasing number of new diagnosed cases appear each year. Long-term therapy and the development of resistance to the drugs used drive the search for more and more new agents with anti-melanoma activity. This review focuses on the most recent synthesized anti-melanoma agents from 2020–2022. For selected agents, apart from the analysis of biological activity, the structure–activity relationship (SAR) is also discussed. To the best of our knowledge, the following literature review delivers the latest achievements in the field of new anti-melanoma agents.

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“…Cinnamic acid esters are found in benzoin balsams [1]. Cinnamic acid esters show biological activities such as antifungal [2], antidiabetic [3], antituberculosis, antimalarial [4], antioxidant [5], antiprotozoal [6], anti-inflammatory [7], and antiproliferative activities [8]. The synthesis of cinnamic acid esters generally involves reactions with thionyl chloride [9], which is one of the chemicals included in the chemical weapon convention (CWC) list [10].…”

Section: Introductionmentioning

confidence: 99%

4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate

Santoso¹,

Pamela²,

Ramadhani³

et al. 2022

Molbank

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4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) was established by FTIR, NMR, and the high resolution of mass spectroscopies. 4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate (1) showed higher α-glucosidase inhibition activity than standard drug acarbose. The molecular docking study exhibited that the title compound 1 had a good affinity for α-glucosidase (PDB ID: 3W37) and formed some interactions with the α-glucosidase active site residue.

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Synthesis of cinnamic acid ester derivatives with antiproliferative and antimetastatic activities on murine melanoma cells

Cited by 20 publications

References 63 publications

Synthesis, Cytotoxicity Evaluation and Molecular Docking Studies of Xanthyl-Cinnamate Derivatives as Potential Anticancer Agents

Synthesis, Cytotoxicity Evaluation and Molecular Docking Studies of Xanthyl-Cinnamate Derivatives as Potential Anticancer Agents

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

4-Methoxyphenethyl (E)-3-(o-tolyl)acrylate

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