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Synthesis and anticancer activity of novel coumarin-stilbene hybrids with different hydrocarbon chains as linkers

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Abstract

Stilbene derivatives (pterostilbene and resveratrol) and 4-methylumbelliferone occur naturally in plants. These compounds and coumarin-stilbene hybrids have a variety of biological activities. It was envisioned that the molecular hybridization strategy would produce new bioactive molecules. Thus, six new coumarin-stilbene hybrids (3a-b, 4a-b, and 5a-b) with different hydrocarbon chains as linkers were synthesized by the O-alkylation reaction and characterized using FTIR, 1H NMR, 13C NMR, DEPT-135, and HRMS (ESI+) spectral analysis. An MTT assay was used to test the synthesized hybrids against breast cancer (MCF-7 and T47D) and liver cancer (HepG2) cell lines. The results showed that the synthesis of coumarin-stilbene hybrids via the O-alkylation reaction requires the presence of KI in addition to K2CO3 as a base to complete the reaction. On the other hand, the synthesis of coumarin-pterostilbene hybrids (3a-b) via the O-alkylation reaction with DMF as a solvent and an excess of base (K2CO3) and catalyst (KI) improved the yield significantly (65.43 and 73.71%, respectively). The biological results exhibited that all hybrids showed moderate to weak anticancer activities, much lower than the medication (cisplatin). However, most compounds showed superior activities than parent compounds against three different human cell lines. Among them, compounds 4a and 4b exhibited the best cytotoxic activity against T47D and MCF-7, with IC50 values of 102.05 and 23.12 µM, respectively. Compound (3a) showed the most cytotoxic activity against HepG2, with an IC50 value of 80.09 µM. To conclude, due to the simplicity of synthesis, hybridization is a promising strategy for producing new hybrid compounds with hydrocarbon chains as linkers and improving biological activity compared with their parent compounds.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Lamya A. Al-lehaib, Khalid O. Al-Footy & Reda M. El-Shishtawy

  2. Department of Chemistry, College of Science, Qassim University, Buraydah, Saudi Arabia

    Lamya A. Al-lehaib

  3. King Fahd Center for Medical Research, King Abdulaziz University, Jeddah, Saudi Arabia

    Lamya A. Al-lehaib

  4. Department of Biochemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Ehab M. M. Ali

  5. Division of Biochemistry, Department of Chemistry, Faculty of Science, Tanta University, Tanta, 31527, Egypt

    Ehab M. M. Ali

  6. Dyeing, Printing and Textile Auxiliaries Department, Textile Research and Technology Institute, National Research Centre, 33 EL Buhouth St., Dokki, Giza, 12622, Egypt

    Reda M. El-Shishtawy

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  1. Lamya A. Al-lehaib
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Al-lehaib, L.A., Ali, E.M.M., Al-Footy, K.O. et al. Synthesis and anticancer activity of novel coumarin-stilbene hybrids with different hydrocarbon chains as linkers. Med Chem Res 33, 764–778 (2024). https://doi.org/10.1007/s00044-024-03212-4

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