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Transformation of Cloprostenol into E-Type Derivatives and a Comparative Study of Their Uterotonic Activity

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Pharmaceutical Chemistry Journal Aims and scope

The racemic methyl ester of 16-(m-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α (cloprostenol) was transformed into corresponding E-type derivatives through the stages of selective protection of the C-11 and C-15 hydroxyls as tert-butyldiphenylsilyl ethers, oxidation of the C-9 alcohol, removal of the protecting silyl groups, and enzymatic hydrolysis of the methyl ester. The E-type acid and corresponding methyl ester thus obtained were tested for uterotonic activity. The results were compared with the activity of the parent cloprostenol and corresponding methyl ester. The E-type prostaglandin methyl ester doubled (p > 0.05) the frequency of contractions of the rat uterine horn compared to the control and appeared to be more effective than the E-type acid and misoprostol (p < 0.05).

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Acknowledgments

The work was financially supported by the RFBR under science project No. 20-33-90114 Post-graduates under state task 122031400261-4.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center (UFRC), Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    V. V. Zagitov, N. S. Vostrikov, T. A. Sapozhnikova & M. S. Miftakhov

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  1. V. V. Zagitov
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  2. N. S. Vostrikov
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  3. T. A. Sapozhnikova
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  4. M. S. Miftakhov
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Correspondence to N. S. Vostrikov.

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 57, No. 1, pp. 19 – 23, January, 2023.

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Zagitov, V.V., Vostrikov, N.S., Sapozhnikova, T.A. et al. Transformation of Cloprostenol into E-Type Derivatives and a Comparative Study of Their Uterotonic Activity. Pharm Chem J 57, 46–50 (2023). https://doi.org/10.1007/s11094-023-02849-6

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  • DOI: https://doi.org/10.1007/s11094-023-02849-6

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