One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors

This study describes the synthesis, characterization, and biological activities of halogenated xanthone, 3-O substituted xanthone, and prenylated xanthone derivatives. The molecular structures of these compounds were identified using 1 H NMR, 13C NMR, 2D NMR, FTIR and DIMS. All synthesized compou...

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Main Authors: Ramakrishnan, Shurutishria, Mad Nasir, Nadiah, Stanslas, Johnson, Faisal Hamdi, Amir Imran, Mohammad Latif, Muhammad Alif, Baharuddin, Fatin Farhana
Format: Article
Published: Elsevier BV 2023
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author Ramakrishnan, Shurutishria
Mad Nasir, Nadiah
Stanslas, Johnson
Faisal Hamdi, Amir Imran
Mohammad Latif, Muhammad Alif
Baharuddin, Fatin Farhana
author_facet Ramakrishnan, Shurutishria
Mad Nasir, Nadiah
Stanslas, Johnson
Faisal Hamdi, Amir Imran
Mohammad Latif, Muhammad Alif
Baharuddin, Fatin Farhana
author_sort Ramakrishnan, Shurutishria
collection UPM
description This study describes the synthesis, characterization, and biological activities of halogenated xanthone, 3-O substituted xanthone, and prenylated xanthone derivatives. The molecular structures of these compounds were identified using 1 H NMR, 13C NMR, 2D NMR, FTIR and DIMS. All synthesized compounds were evaluated against two cancer cell lines: breast adenocarcinoma MCF-7 and MDA-MB-231 by application of the MTT assay. With this approach, xanthones 9 and 13 were identified as putative aromatase activating agents through the inhibition of interactions with MCF-7 and MDA-MB-231. The selected compounds, 9 and 13, were further examined for toxicity against the African Green Monkey Kidney cell (VERO) and Non-tumorigenic Lung Epithelial cell lines (BEAS-2B). In addition, in-silico docking studies were conducted to estimate the binding poses and residues implicated in probable MCF-7 and MDA-MB-231 interactions.
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spelling upm.eprints-1092652024-08-16T07:57:09Z http://psasir.upm.edu.my/id/eprint/109265/ One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors Ramakrishnan, Shurutishria Mad Nasir, Nadiah Stanslas, Johnson Faisal Hamdi, Amir Imran Mohammad Latif, Muhammad Alif Baharuddin, Fatin Farhana This study describes the synthesis, characterization, and biological activities of halogenated xanthone, 3-O substituted xanthone, and prenylated xanthone derivatives. The molecular structures of these compounds were identified using 1 H NMR, 13C NMR, 2D NMR, FTIR and DIMS. All synthesized compounds were evaluated against two cancer cell lines: breast adenocarcinoma MCF-7 and MDA-MB-231 by application of the MTT assay. With this approach, xanthones 9 and 13 were identified as putative aromatase activating agents through the inhibition of interactions with MCF-7 and MDA-MB-231. The selected compounds, 9 and 13, were further examined for toxicity against the African Green Monkey Kidney cell (VERO) and Non-tumorigenic Lung Epithelial cell lines (BEAS-2B). In addition, in-silico docking studies were conducted to estimate the binding poses and residues implicated in probable MCF-7 and MDA-MB-231 interactions. Elsevier BV 2023-01 Article PeerReviewed Ramakrishnan, Shurutishria and Mad Nasir, Nadiah and Stanslas, Johnson and Faisal Hamdi, Amir Imran and Mohammad Latif, Muhammad Alif and Baharuddin, Fatin Farhana (2023) One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors. Results in Chemistry, 5. art. no. 100789. pp. 1-11. ISSN 2211-7156 https://linkinghub.elsevier.com/retrieve/pii/S2211715623000280 10.1016/j.rechem.2023.100789
spellingShingle Ramakrishnan, Shurutishria
Mad Nasir, Nadiah
Stanslas, Johnson
Faisal Hamdi, Amir Imran
Mohammad Latif, Muhammad Alif
Baharuddin, Fatin Farhana
One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors
title One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors
title_full One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors
title_fullStr One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors
title_full_unstemmed One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors
title_short One-pot two-component synthesis of halogenated xanthone, 3-o substituted xanthone, and prenylated xanthone derivatives as aromatase inhibitors
title_sort one pot two component synthesis of halogenated xanthone 3 o substituted xanthone and prenylated xanthone derivatives as aromatase inhibitors
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