Cargando…
Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents
A new oxidant, containing m-chloroperoxybenzoic acid (MCPBA) and an iron salt, was developed and used for oxidation of steroidal phenols to a quinol/epoxyquinol mixture. Reaction was optimized for estrone, by varying initiators (Fe-salts), reaction temperature, time and mode of MCPBA application. A...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9290445/ https://www.ncbi.nlm.nih.gov/pubmed/35919136 http://dx.doi.org/10.1039/d2ra03717c |
_version_ | 1784748901920669696 |
---|---|
author | Kop, Tatjana J. Terzić-Jovanović, Nataša Žižak, Željko Šolaja, Bogdan A. Milić, Dragana R. |
author_facet | Kop, Tatjana J. Terzić-Jovanović, Nataša Žižak, Željko Šolaja, Bogdan A. Milić, Dragana R. |
author_sort | Kop, Tatjana J. |
collection | PubMed |
description | A new oxidant, containing m-chloroperoxybenzoic acid (MCPBA) and an iron salt, was developed and used for oxidation of steroidal phenols to a quinol/epoxyquinol mixture. Reaction was optimized for estrone, by varying initiators (Fe-salts), reaction temperature, time and mode of MCPBA application. A series of five more substrates (17β-estradiol and its hydrophobized derivatives) was subjected to the optimized oxidation, providing corresponding p-quinols and 4β,5β-epoxyquinols in good to moderate yields. The obtained epoxyquinols were additionally transformed by oxidation, as well as the acid-catalyzed oxirane opening. In a preliminary study of the antiproliferative activity against human cancer cell lines, all newly synthesized compounds expressed moderate to high activity. |
format | Online Article Text |
id | pubmed-9290445 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-92904452022-08-01 Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents Kop, Tatjana J. Terzić-Jovanović, Nataša Žižak, Željko Šolaja, Bogdan A. Milić, Dragana R. RSC Adv Chemistry A new oxidant, containing m-chloroperoxybenzoic acid (MCPBA) and an iron salt, was developed and used for oxidation of steroidal phenols to a quinol/epoxyquinol mixture. Reaction was optimized for estrone, by varying initiators (Fe-salts), reaction temperature, time and mode of MCPBA application. A series of five more substrates (17β-estradiol and its hydrophobized derivatives) was subjected to the optimized oxidation, providing corresponding p-quinols and 4β,5β-epoxyquinols in good to moderate yields. The obtained epoxyquinols were additionally transformed by oxidation, as well as the acid-catalyzed oxirane opening. In a preliminary study of the antiproliferative activity against human cancer cell lines, all newly synthesized compounds expressed moderate to high activity. The Royal Society of Chemistry 2022-07-18 /pmc/articles/PMC9290445/ /pubmed/35919136 http://dx.doi.org/10.1039/d2ra03717c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Kop, Tatjana J. Terzić-Jovanović, Nataša Žižak, Željko Šolaja, Bogdan A. Milić, Dragana R. Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
title | Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
title_full | Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
title_fullStr | Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
title_full_unstemmed | Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
title_short | Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
title_sort | iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9290445/ https://www.ncbi.nlm.nih.gov/pubmed/35919136 http://dx.doi.org/10.1039/d2ra03717c |
work_keys_str_mv | AT koptatjanaj ironsaltpromotedoxidationofsteroidalphenolsbymchloroperbenzoicacidaroutetopossibleantitumoragents AT terzicjovanovicnatasa ironsaltpromotedoxidationofsteroidalphenolsbymchloroperbenzoicacidaroutetopossibleantitumoragents AT zizakzeljko ironsaltpromotedoxidationofsteroidalphenolsbymchloroperbenzoicacidaroutetopossibleantitumoragents AT solajabogdana ironsaltpromotedoxidationofsteroidalphenolsbymchloroperbenzoicacidaroutetopossibleantitumoragents AT milicdraganar ironsaltpromotedoxidationofsteroidalphenolsbymchloroperbenzoicacidaroutetopossibleantitumoragents |