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Synthesis, cytotoxicity, and antitubercular studies of novel thiophene containing 2-methyl-3-methyl/ethyl acrylates from Baylis–Hillman adducts

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Abstract

Herein, we describe the synthesis, cytotoxicity effect and antitubercular activity of thiophene containing Baylis–Hillman adducts (2al), Baylis–Hillman bromides (3al) and 2-methyl-3-methyl/ethyl acrylates (4al). Their structures were elucidated by elemental analysis, IR, 1H NMR, 13C NMR, and mass spectroscopic data. All the compounds were evaluated for their in vitro cytotoxicity effect using the MTT assay method against two human cancer cell lines (MCF-7 and K562). The compounds demonstrated a growth inhibitory effect on both the cell lines with significant IC50 values. Among the compounds synthesized, 3h and 4g showed excellent activities on both the cell lines, whereas the other compounds exhibited moderate activity. The antitubercular activity of the obtained compounds was tested against Mycobacterium tuberculosis H37Rv in vitro using the agar microdilution method. Sevenfold dilutions ranging between 0.65 and 50 μg/ml of each test compound were used to find out their minimum inhibitory concentration. Among the tested compounds, compound 3l showed almost equal activity with the standard drug Isoniazid (INH), whereas the rest of all compounds have shown less to moderate activity against Mycobacterium tuberculosis H37Rv.

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Acknowledgements

The authors are grateful for the financial support from the office of the research affairs, Haramaya University, Ethiopia under the mega project HURG-2016-03-02.

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Correspondence to Neelaiah Babu G..

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G., N.B., Tadesse, A., Wote, A. et al. Synthesis, cytotoxicity, and antitubercular studies of novel thiophene containing 2-methyl-3-methyl/ethyl acrylates from Baylis–Hillman adducts. Med Chem Res 29, 409–416 (2020). https://doi.org/10.1007/s00044-019-02489-0

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Keywords

  • Thiophene
  • 2-methyl-3-methyl/ethyl acrylates
  • Baylis–Hillman adducts
  • Baylis–Hillman bromides
  • Cytotoxicity
  • Antitubercular activity