Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents
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Iron salt-promoted reaction of estrone and its derivatives with meta -chloroperoxybenzoic acid was developed and epoxyquinols were further transformed. Most compounds showed in vitro antiproliferative activity. , 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 prel...iminary study of the antiproliferative activity against human cancer cell lines, all newly synthesized compounds expressed moderate to high activity.
Извор:
RSC AdvancesRSC Adv., 2022, 12, 32, 20649-20655Издавач:
- Royal Society of Chemistry
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Serbian Academy of Sciences and Arts (grant F80)
DOI: 10.1039/D2RA03717C
ISSN: 2046-2069
WoS: 00082654250000
Scopus: 2-s2.0-85135849583
URI
https://pubs.rsc.org/en/content/articlelanding/2022/ra/d2ra03717chttp://cherry.chem.bg.ac.rs/handle/123456789/5523
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Kop, Tatjana J. AU - Terzić-Jovanović, Nataša AU - Žižak, Željko AU - Šolaja, Bogdan A. AU - Milić, Dragana R. PY - 2022 UR - https://pubs.rsc.org/en/content/articlelanding/2022/ra/d2ra03717c UR - http://cherry.chem.bg.ac.rs/handle/123456789/5523 AB - Iron salt-promoted reaction of estrone and its derivatives with meta -chloroperoxybenzoic acid was developed and epoxyquinols were further transformed. Most compounds showed in vitro antiproliferative activity. , 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. PB - Royal Society of Chemistry T2 - RSC AdvancesRSC Adv. T1 - Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents VL - 12 IS - 32 SP - 20649 EP - 20655 DO - 10.1039/D2RA03717C ER -
@article{ author = "Kop, Tatjana J. and Terzić-Jovanović, Nataša and Žižak, Željko and Šolaja, Bogdan A. and Milić, Dragana R.", year = "2022", abstract = "Iron salt-promoted reaction of estrone and its derivatives with meta -chloroperoxybenzoic acid was developed and epoxyquinols were further transformed. Most compounds showed in vitro antiproliferative activity. , 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.", publisher = "Royal Society of Chemistry", journal = "RSC AdvancesRSC Adv.", title = "Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents", volume = "12", number = "32", pages = "20649-20655", doi = "10.1039/D2RA03717C" }
Kop, T. J., Terzić-Jovanović, N., Žižak, Ž., Šolaja, B. A.,& Milić, D. R.. (2022). Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents. in RSC AdvancesRSC Adv. Royal Society of Chemistry., 12(32), 20649-20655. https://doi.org/10.1039/D2RA03717C
Kop TJ, Terzić-Jovanović N, Žižak Ž, Šolaja BA, Milić DR. Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents. in RSC AdvancesRSC Adv.. 2022;12(32):20649-20655. doi:10.1039/D2RA03717C .
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" in RSC AdvancesRSC Adv., 12, no. 32 (2022):20649-20655, https://doi.org/10.1039/D2RA03717C . .