Iron salt-promoted oxidation of steroidal phenols by m-chloroperbenzoic acid: a route to possible antitumor agents
- 1. University of Belgrade, Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, 11000 Belgrade, Republic of Serbia
- 2. University of Belgrade, Institute for Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, Serbia
- 3. University of Belgrade, Faculty of Chemistry, Studentski trg 12-16, 11158 Belgrade, Serbia ; Serbian Academy of Sciences and Arts, Knez Mihailova 35, 11000 Belgrade, Serbia
- 4. University of Belgrade, Faculty of Chemistry, Studentski trg 12-16, 11158 Belgrade, Serbia
Description
Abstract. 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.
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Additional details
Related works
- Is derived from
- rsc.li/rsc-advances (Handle)
- Is documented by
- 35919136 (PMID)
- Is identical to
- PMC9290445 (pmcid)
- Is part of
- 2046-2069 (ISSN)
- Is supplemented by
- https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9290445/pdf/RA-012-D2RA03717C.pdf (URL)
Funding
- Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) 200026
- Ministry of Education, Science and Technological Development