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Synthesis and cytotoxic activity of substituted hexahydro-2H-4,6-(epoxymethano)chromen-8(5H)-ones obtained from (–)-verbenone

Abstract

A number of compounds with a substituted hexahydro-2H-4,6-(epoxymethano)chromen8(5H)-one framework was synthesized starting from monoterpenoid (–)-verbenone and aromatic aldehydes containing methoxy and hydroxy groups. Cytotoxic activity of these compounds on human tumor cell lines was studied for the first time. Compounds containing three methoxy groups in each aromatic ring were found to be the most promising for further studies.

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Correspondence to K. P. Volcho.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2257–2260, September, 2015.

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Il’ina, I.V., Pokrovsky, M.A., Mikhalchenko, O.S. et al. Synthesis and cytotoxic activity of substituted hexahydro-2H-4,6-(epoxymethano)chromen-8(5H)-ones obtained from (–)-verbenone. Russ Chem Bull 64, 2257–2260 (2015). https://doi.org/10.1007/s11172-015-1148-3

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  • DOI: https://doi.org/10.1007/s11172-015-1148-3

Key words

  • monoterpene
  • cytotoxicity
  • verbenone
  • clay
  • heterocyclic compounds