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Methyl (S)-(5-methylidene-4-oxocyclopent-2-en-1-yl)acetate as a readily available pharmacologically important subunit of cross-conjugated cyclopentenone prostaglandins

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Abstract

A short and convenient synthesis of exomethylidenecyclopentenone core of cyclopentenone prostaglandins (+)−3 from (−) Corey lactone diol is described. The chiral 5-phenylthio and 5-phenylsulfonyl derivatives of exomethylidenecyclopentenone were obtained and their cytotoxic properties were studied in comparison with the synthesized earlier ethylthio and ethylsulfonyl derivatives of (±)−3, announced as its more stable bioisosteres.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Scientific Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    N. S. Vostrikov, Z. R. Makaev, V. V. Zagitov & M. S. Miftakhov

  2. Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus, Minsk, Belarus

    F. A. Lakhvich & F. S. Pashkovsky

Authors
  1. N. S. Vostrikov
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  2. Z. R. Makaev
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  3. V. V. Zagitov
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  4. F. A. Lakhvich
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  5. F. S. Pashkovsky
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  6. M. S. Miftakhov
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Additional information

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

This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-53-00011 Bel_а) in the framework of the Russian state assignment АААА-А17-117011910032-4.

PRESS RELEASE No. 24, International Agency for Research on Cancer. World Health Organization, Lion—London, February 3, 2014.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0547–0551, March, 2020.

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Vostrikov, N.S., Makaev, Z.R., Zagitov, V.V. et al. Methyl (S)-(5-methylidene-4-oxocyclopent-2-en-1-yl)acetate as a readily available pharmacologically important subunit of cross-conjugated cyclopentenone prostaglandins. Russ Chem Bull 69, 547–551 (2020). https://doi.org/10.1007/s11172-020-2796-5

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  • DOI: https://doi.org/10.1007/s11172-020-2796-5

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