Kop Tatjana J, Terzić-Jovanović Nataša, Žižak Željko, Šolaja Bogdan A, Milić Dragana R
University of Belgrade, Institute of Chemistry, Technology and Metallurgy, Department of Chemistry Njegoševa 12 11000 Belgrade Republic of Serbia
University of Belgrade, Institute for Oncology and Radiology of Serbia Pasterova 14 11000 Belgrade Serbia.
RSC Adv. 2022 Jul 18;12(32):20649-20655. doi: 10.1039/d2ra03717c. eCollection 2022 Jul 14.
A new oxidant, containing -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 -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.
一种新的氧化剂，包含间氯过氧苯甲酸（MCPBA）和一种铁盐，被研发出来并用于将甾体酚氧化为喹诺醇/环氧喹诺醇混合物。通过改变引发剂（铁盐）、反应温度、时间和MCPBA的应用方式，对雌酮的反应进行了优化。另外五种底物（17β-雌二醇及其疏水化衍生物）进行了优化氧化反应，以良好至中等的产率得到了相应的喹诺醇和4β,5β-环氧喹诺醇。所得到的环氧喹诺醇还通过氧化以及酸催化的环氧乙烷开环进行了进一步转化。在针对人类癌细胞系的抗增殖活性的初步研究中，所有新合成的化合物都表现出中等至高活性。
