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Synthesis of novel GABA-Triazole tethered derivatives of Noscapine and their anticancer activities

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Abstract

Synthesis of novel noscapine triazole tethered derivatives with γ-aminobutyric acid (GABA) linker is reported. Attachment of the linker was done by N-demethylation of noscapine followed by coupling with N-Boc protected GABA. The straightforward synthesis of the target molecules was made by a three-component reaction between GABA-noscapine, p-nitrophenyl azide, and commercially available ketones under metal-free conditions to produce a library with diverse functional groups. Anticancer activity of the synthesized derivatives was evaluated on MCF-7 cancer cell line. The best anticancer activity was demonstrated by a compound with an IC50 value of 57.2 µM, close to that of noscapine (IC50 = 55.2 µM).

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Acknowledgements

We are grateful to Shahid Beheshti University Research Council for partial financial support of this work.

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Authors and Affiliations

  1. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, 1983963113, Iran

    Farzaneh Karimi, Peyman Salehi & Morteza Bararjanian

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  1. Farzaneh Karimi
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  2. Peyman Salehi
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  3. Morteza Bararjanian
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Correspondence to Peyman Salehi.

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Karimi, F., Salehi, P. & Bararjanian, M. Synthesis of novel GABA-Triazole tethered derivatives of Noscapine and their anticancer activities. Monatsh Chem 155, 195–203 (2024). https://doi.org/10.1007/s00706-024-03170-y

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  • DOI: https://doi.org/10.1007/s00706-024-03170-y

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