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Synthesis and cytotoxic activity of isocembrol and its hydroxy derivatives

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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).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Centre, Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    Sh. M. Salikhov, L. Kh. Faizullina & F. A. Valeev

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  1. Sh. M. Salikhov
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  2. L. Kh. Faizullina
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  3. F. A. Valeev
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Correspondence to L. Kh. Faizullina.

Additional information

The study was financially supported by the Russian Foundation for Basic Research (Project No. 17-43-020166-r_a) and performed within the framework of the state assignment (themes AAAA-A20-120012090028-3 and AAAA-A17-117011910027-0).

Russian Chemical Bulletin, International Edition, Vol. 69, No. 10, pp. 1933–1937, October, 2020

Published in Russian in Izvestiya AkademiiNauk. Seriya Khimicheskaya, No. 10, pp. 1933–1937, October, 2020.

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Salikhov, S.M., Faizullina, L.K. & Valeev, F.A. Synthesis and cytotoxic activity of isocembrol and its hydroxy derivatives. Russ Chem Bull 69, 1933–1937 (2020). https://doi.org/10.1007/s11172-020-2981-6

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  • DOI: https://doi.org/10.1007/s11172-020-2981-6

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