Synthesis of 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone as a candidate anticancer against cervical (WiDr), colon (HeLa), and breast (T47d) cancer cell lines in vitro

Matsjeh, Sabirin; Swasono, Respati Tri; Anwar, Chairil; Solikhah, Eti Nurwening; Lestari, Endang Gati

doi:10.1063/1.4978121

Cited by 2 publications

(2 citation statements)

References 8 publications

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“…derivative was carried out using the procedure from Matsjeh et al [14]. First, 2,4-Dihydroxyacetophenone (3 mmol) was dissolved with 10 mL of methanol in a three-neck round bottom flask, 15 mL of 40% KOH solution was added slowly until the solution was homogeneous.…”

Section: Synthesis Of 2'4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalco...mentioning

confidence: 99%

“…The addition of montmorillonite KSF catalyst in this reaction is thought to cause the interaction between the H atoms of the hydroxy group attached to 3-bromo-4-hydroxy-5-methoxybenzaldehyde with the O atoms of alumina silicate and H2O molecules contained in the KSF montmorillonite catalyst interlayer through the formation of hydrogen bonds. This interaction causes the H atom in the hydroxy group of the vanillin compound not to be easily separated even in the presence of KOH so that the formation of vanillate ions can be avoided [14]. 1 H-NMR and 13 C-NMR confirmed the presence of H and C atoms.…”

Section: Fig 1 Synthesis Of Benzaldehyde and Chalcone Derivativesmentioning

confidence: 99%

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Synthesis of Chalcone Derivatives from Halogenated Vanillin and their Activity Test as Antioxidant

Rijal

Haryadi

Anwar

2022

MSF

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Synthesis of 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalcone and evaluation of their antioxidant activity have been carried out. 3-Chloro-4-hydroxy-5-methoxybenzaldehyde was obtained through chlorination of vanillin using Ca(ClO)2, while 3-bromo-4-hydroxy-5-methoxybenzaldehyde was obtained via bromination of vanillin using KBrO3 in glacial acetic acid solvent and 47% HBr catalyst. Then, 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxychalcone was prepared from 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2-4-dihydroxyacetophenone through Claisen-Schmidt condensation in the presence of KOH (40%) base and KSF montmorillonite in methanol. Elucidation of the structure of these compounds was performed using FTIR, GC-MS, TLC-Scanner, MS-Direct, 1H-NMR, and 13C-NMR. The synthesized benzaldehydes and chalcone were tested for their antioxidant activities using DPPH method, where 2,6-di-tert-butyl-4-methylphenol (BHT) was used as positive control. The results showed that 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalcone were obtained in 53%, 97%, and 1%, respectively. The antioxidant activity assay showed that BHT, 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalcone displayed the IC50 of 27.94, 244.11, 269.44 and 162.10 µg/mL, respectively.

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Section: Synthesis Of 2'4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalco...mentioning

confidence: 99%

Section: Fig 1 Synthesis Of Benzaldehyde and Chalcone Derivativesmentioning

confidence: 99%

Synthesis of Chalcone Derivatives from Halogenated Vanillin and their Activity Test as Antioxidant

Rijal

Haryadi

Anwar

2022

MSF

Self Cite

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Experimental and DFT studies on 2′,4′-dihydroxychalcone, a product isolated from Zuccagnia punctata Cav. (Fabaceae) medicinal plant

Chahar

Álvarez

Zampini

et al. 2020

Journal of Molecular Structure

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Synthesis of 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone as a candidate anticancer against cervical (WiDr), colon (HeLa), and breast (T47d) cancer cell lines in vitro

Cited by 2 publications

References 8 publications

Synthesis of Chalcone Derivatives from Halogenated Vanillin and their Activity Test as Antioxidant

Synthesis of Chalcone Derivatives from Halogenated Vanillin and their Activity Test as Antioxidant

Experimental and DFT studies on 2′,4′-dihydroxychalcone, a product isolated from Zuccagnia punctata Cav. (Fabaceae) medicinal plant

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