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Design, synthesis, estrogenic and antiestrogenic activities of some triarylpyrazole derivatives

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Abstract

New triarylpyrazole derivatives, substituted with basic side chain, polar group or heterocyclic ring were designed and synthesized. Nineteen compounds were tested for their in vivo uterotrophic activity. Animals treated with compounds 9, 15a, 15c, 19a, 19f, 20a, and 21b showed pronounced increase in uterine weight. It is worth mentioning that compound 19f was more active than estradiol as an estrogenic compound as evidenced by the increased dry uterine weight. Additionally, compound 19a produced 128.25% increase in dry uterine weight relative to estradiol. On the other hand, eight compounds were screened for their in vivo antiuterotrophic activity. Animals treated with compounds 5e, 5f, 8, and 13b showed pronounced decrease in uterine weight. The highest antiuterotrophic effect was observed in mice receiving compound 13b, which was as potent as the positive control, tamoxifen as evident by the decrease in the uterine wet weight.

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Acknowledgements

The authors are thankful to N.M. Andijani for her assistance in in vivo experiments.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Damanhour University, Damanhour, Egypt

    Mahmoud A. Ragab

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria, 21521, Egypt

    Heba A. Abd El Razik, Khadiga A. Ismail, Mounir A. Khalil & Nargues S. Habib

  3. Department of Pharmacology, Faculty of Pharmacy, King Abdulaziz University, PO 80260, Jeddah, 21589, Saudi Arabia

    Elham A. Afify

  4. Department of Pharmacology, Faculty of Pharmacy, Alexandria University, Alexandria, 21521, Egypt

    Elham A. Afify

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  1. Mahmoud A. Ragab
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  2. Heba A. Abd El Razik
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  3. Elham A. Afify
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  4. Khadiga A. Ismail
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  5. Mounir A. Khalil
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  6. Nargues S. Habib
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Correspondence to Heba A. Abd El Razik.

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Ragab, M.A., Abd El Razik, H.A., Afify, E.A. et al. Design, synthesis, estrogenic and antiestrogenic activities of some triarylpyrazole derivatives. Med Chem Res 26, 2785–2808 (2017). https://doi.org/10.1007/s00044-017-1977-8

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  • DOI: https://doi.org/10.1007/s00044-017-1977-8

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