Limitation of Algar–Flynn–Oyamada reaction using methoxy substituted chalcones as reactants and evaluation of the newly transformed aurones for their biological activities

Sukriti Nigam, B. S. Jayashree

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Abstract

The study describes newly synthesized 7-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4,6-dimethoxy aurones (SJA 1–14) obtained as final compounds by the oxidative cyclisation of chalcone intermediates in the presence of alkaline hydrogen peroxide catalyst. Their structures were confirmed by spectral analysis and were further evaluated for their in vitro antioxidant and anticancer activities. To support their physicochemical characteristics, distribution coefficients (log D7.4) and oxidation potentials (Epa) were determined. Among the test compounds, SJA 8 and SJA 11 were found cytotoxic to MCF-7, T47D and MDA MB-231 in the IC50 range of 16.63 ± 1.00–43.93 ± 2.09 µM when compared to doxorubicin in the IC50 range of 0.23 ± 0.03–8.32 ± 0.46 µM. Further studies performed with SJA 8 and SJA 11 on MCF-7 showed that they significantly increased the apoptotic index as compared to the control and displayed a G0/G1 phase arrest of the cell cycle. It was observed that synthesised aurones possessing para substitution on ring B showed cytotoxic activity and possessed log D7.4 in the range of 2.5–3.2. Conversely, radical scavenging activity of aurones was in the IC50 range of 71.67 ± 0.24 to >1000 µM when compared to ascorbic acid and quercetin in the IC50 range of 15.46 ± 1.30–34.42 ± 0.03 µM. However, their low antioxidant potential was supported by their high Epa values in the range of 0.926–1.008 V when compared to standard antioxidants. Further studies on N-benzyl tetrahydropyridinyl-4,6-dimethoxy substituted aurones would create a platform for understanding their optimum structural features and the extent to which they may be useful as anticancer agents.

Original languageEnglish
Pages (from-to)2839-2864
Number of pages26
JournalResearch on Chemical Intermediates
Volume43
Issue number5
DOIs
Publication statusPublished - 01-05-2017

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Chalcones
Bioactivity
Antioxidants
Chalcone
Cyclization
Scavenging
Quercetin
Antineoplastic Agents
Doxorubicin
Spectrum analysis
Hydrogen Peroxide
Ascorbic Acid
Substitution reactions
Cells
Oxidation
Catalysts
aurone

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Limitation of Algar–Flynn–Oyamada reaction using methoxy substituted chalcones as reactants and evaluation of the newly transformed aurones for their biological activities",
abstract = "The study describes newly synthesized 7-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4,6-dimethoxy aurones (SJA 1–14) obtained as final compounds by the oxidative cyclisation of chalcone intermediates in the presence of alkaline hydrogen peroxide catalyst. Their structures were confirmed by spectral analysis and were further evaluated for their in vitro antioxidant and anticancer activities. To support their physicochemical characteristics, distribution coefficients (log D7.4) and oxidation potentials (Epa) were determined. Among the test compounds, SJA 8 and SJA 11 were found cytotoxic to MCF-7, T47D and MDA MB-231 in the IC50 range of 16.63 ± 1.00–43.93 ± 2.09 µM when compared to doxorubicin in the IC50 range of 0.23 ± 0.03–8.32 ± 0.46 µM. Further studies performed with SJA 8 and SJA 11 on MCF-7 showed that they significantly increased the apoptotic index as compared to the control and displayed a G0/G1 phase arrest of the cell cycle. It was observed that synthesised aurones possessing para substitution on ring B showed cytotoxic activity and possessed log D7.4 in the range of 2.5–3.2. Conversely, radical scavenging activity of aurones was in the IC50 range of 71.67 ± 0.24 to >1000 µM when compared to ascorbic acid and quercetin in the IC50 range of 15.46 ± 1.30–34.42 ± 0.03 µM. However, their low antioxidant potential was supported by their high Epa values in the range of 0.926–1.008 V when compared to standard antioxidants. Further studies on N-benzyl tetrahydropyridinyl-4,6-dimethoxy substituted aurones would create a platform for understanding their optimum structural features and the extent to which they may be useful as anticancer agents.",
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