N. S. Vostrikov, L. V. Spirikhin, A. N. Lobov, A. M. Gimazetdinov, Z. R. Zileeva, Yu. V. Vakhitova, Z. R. Macaev, K. K. Pivnitsky, M. S. Miftakhov, “Simple antitumor model compounds for cross-conjugated cyclopentenone prostaglandins”, Mendeleev Commun., 2019, Volume 29, Issue 4,Pages <nobr>372

This article is cited in 11 papers

Communications

Simple antitumor model compounds for cross-conjugated cyclopentenone prostaglandins

N. S. Vostrikov^a, L. V. Spirikhin^a, A. N. Lobov^a, A. M. Gimazetdinov^a, Z. R. Zileeva^b, Yu. V. Vakhitova^b, Z. R. Macaev^a, K. K. Pivnitsky^c, M. S. Miftakhov^a

^a Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
^b Institute of Biochemistry and Genetics, Ufa Federal Research Center of the Russian Academy of Sciences, Ufa, Russian Federation
^c N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Unstable methyl (5-methylidene-4-oxocyclopent-2-en-1-yl)acetate, having a ring moiety of J-type prostaglandins (PGJs) and similar cytotoxicity, reacts with EtSH and other thiols with formation of mono-and bis-adducts, which have been further converted by oxidation with mCPBA into corresponding stable mono-sulfones possessing cytotoxic effect most probably due to in vivo regeneration of the starting dienone. Thus, the derived sulfones can be used as transport forms for original dienone as a pharmacologically important moiety of Δ¹²-PGJ₂ and similar prostaglandins.

Language: English

DOI: 10.1016/j.mencom.2019.07.003

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