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Synthesis and anticancer evaluation of novel isoxazole/pyrazole derivatives

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Abstract

The key intermediate 3-amino-5-methylisoxazole (1) was allowed to react with phthalic anhydride and/or maleic anhydride under different conditions to produce different isoxazole products. Schiff bases 9a–c obtained via the reaction of 1 with different aldehydes were condensed with thioglycolic acid to afford the corresponding thiazolidin-4-one derivatives 10a, b. Furthermore, condensation of the Schiff bases 9a, c with various secondary amines produced the corresponding 5-substituted pyrazole derivatives 11a–d, respectively. The anticancer activity of some of the newly synthesized compounds was evaluated against Panc-1 and Caco-2 cell lines using doxorubicin as a standard drug. Most of the tested derivatives exhibited high cytotoxic potency against Panc-1 carcinoma cell lines, but moderate to weak activity was obtained against Caco-2 cell lines.

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Authors and Affiliations

  1. Chemistry of Natural and Microbial Products, National Research Centre, Dokki, Cairo, Egypt

    Sherifa M. Abu Bakr

  2. Therapeutical Chemistry Department, National Research Centre, Dokki, Cairo, 12622, Egypt

    Somaia S. Abd El-Karim

  3. Organometallic and Organometaloid Chemistry, National Research Centre, Dokki, Cairo, Egypt

    Medhat M. Said

  4. Biochemistry and Molecular Biology Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt

    Mahmoud M. Youns

Authors
  1. Sherifa M. Abu Bakr
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  2. Somaia S. Abd El-Karim
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  4. Mahmoud M. Youns
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Correspondence to Somaia S. Abd El-Karim.

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Abu Bakr, S.M., Abd El-Karim, S.S., Said, M.M. et al. Synthesis and anticancer evaluation of novel isoxazole/pyrazole derivatives. Res Chem Intermed 42, 1387–1399 (2016). https://doi.org/10.1007/s11164-015-2091-5

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  • DOI: https://doi.org/10.1007/s11164-015-2091-5

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