Synthesis, characterization and molecular docking of chloro-substituted hydroxyxanthone derivatives

Yuanita Emmy; Dwi Pranowo Harno; Mustofa Mustofa; Tri Swasono Respati; Syahri Jufriza; Jumina Jumina

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Reacţii chimice. Procese chimice speciale (67)

Chimie organică (484)

Fiziologia plantelor (526)

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YUANITA, Emmy, DWI PRANOWO, Harno, MUSTOFA, Mustofa, TRI SWASONO, Respati, SYAHRI, Jufriza, JUMINA, Jumina. Synthesis, characterization and molecular docking of chloro-substituted hydroxyxanthone derivatives. In: Chemistry Journal of Moldova, 2019, nr. 1(14), pp. 68-76. ISSN 1857-1727. DOI: https://doi.org/10.19261/cjm.2018.520

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Chemistry Journal of Moldova

Numărul 1(14) / 2019 / ISSN 1857-1727 /ISSNe 2345-1688

Synthesis, characterization and molecular docking of chloro-substituted hydroxyxanthone derivatives

DOI:https://doi.org/10.19261/cjm.2018.520

CZU: 542.943+547.815+581.198

Pag. 68-76

Yuanita Emmy¹², Dwi Pranowo Harno², Mustofa Mustofa², Tri Swasono Respati², Syahri Jufriza³, Jumina Jumina²

¹ Mataram University,
² Gadjah Mada University,
³ Muhammadiyah Riau University

Disponibil în IBN: 10 iulie 2019

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Xanthone compounds are of great interest due to their wide range of biological applications. Xanthone compounds can be obtained by structural modification of the substituent on the xanthone rings through various reactions. In this study, the chloro-substituted hydroxyxanthones (4a-c) were prepared by cyclodehydration of acid derivatives and substituted phenol in the presence of Eaton reagent to afford 3a-c, followed by halogenation step to electrophilic substitution of chlorine in a moderate yield. The in vitro anticancer activity study on various cell lines showed that there was an enhanced activity of compounds 4a-c in comparison to 3a-c. It has been shown that compounds 4a-c have the best anticancer activity only toward P388 murine leukaemia cells with IC50 of 3.27, 1.809 and 0.18 μg/mL, respectively. The results revealed that the chloro functional group increases the anticancer activity of the hydroxyxanthone derivatives. As for the selectivity index, the number was increased from a range of 0.88-843 (3a-c) to 3.33-9199.67 (4a-c). This result indicates that the hydroxyxanthone derivatives (4a-c) have potential to be developed into chemotherapy agents due to their higher sensitivity and selectivity. Molecular docking studies showed that there was a binding interaction between 4c and the amino acid residues such as Asp810, Cys809, Ile789, His790, and Leu644 of protein tyrosine kinase receptor (PDB ID: 1T46).

Cuvinte-cheie
Chlorination, chloro-substituted hydroxyxanthone, derivative, anticancer, Molecular docking

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