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The synthesis of 2- and 3-hydroxy derivatives of isocembrol was accomplished by the epoxidation of isocembrol with tert-butyl hydroperoxide in the presence of a catalytic amount of VO(acac)2 followed by… Click to show full abstract
The synthesis of 2- and 3-hydroxy derivatives of isocembrol was accomplished by the epoxidation of isocembrol with tert-butyl hydroperoxide in the presence of a catalytic amount of VO(acac)2 followed by the epoxide ring opening in the presence of LiAlH4. The 13-hydroxy derivative of isocembrol was synthesized by the allylic oxidation in the SeO2-ButOOH system. Using the PASS software, the 13-hydroxy derivative was predicted to be the most effective cytotoxic agent, which was esterified to form N-methylurocanate. Isocembrol exhibited the highest in vitro antitumor activity against the LOX IMVI (melanoma) and UO-31 (renal cancer) cells, causing up to 25.77 and 75.65% cell death, respectively. N-Methylurocanate led to the death of up to 51.04% UO-31 cells (renal cancer).
Journal Title: Russian Chemical Bulletin
Year Published: 2020
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