Synthesis and biological activities of 3-aminoimidazo[1,2-α]pyridine compounds

Despite their importance in cancer treatment, anticancer compounds face significant challenges due to drug resistance and low specificity, creating an urgent need for the discovery of more effective alternative. Herein, we report the synthesis of eleven 3-aminoimidazole[1,2-α]pyridine compounds (9-19) employing the one-pot Groebke-Blackburn-Bienayme three-component reaction (GBB-3CR). The cytotoxicity of the synthesised compounds was evaluated against three cancer cell lines (MCF-7, HT-29, B16F10) and a normal cell (MEF). Considering effectiveness and safety, the results demonstrated that among the eleven synthesised compounds, only compounds 12 and 14 exhibited high inhibitory activity against cancer cell lines. Compound 12 with a nitro group at the C-2 position and a p-chlorophenyl group at C-3 position, showed the highest inhibitory activity against HT-29, with an IC<sub>50</sub> of 4.15 ± 2.93 µM. Additionally, compound 14, with a tolyl moiety at the C-2 position and a p-chlorophenyl amine at C-3 position, can also be considered a promising bioactive product against B16F10, with an IC<sub>50</sub> of 21.75 ± 0.81 µM. Further research on these compounds may yield more potent candidates for the development of new anticancer agents.

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Publication Details

Journal
BMC Chemistry
Published
2025-02-22
DOI
https://doi.org/10.1186/s13065-025-01412-6
Primary Topic
Synthesis and Reactivity of Heterocycles
Type
article
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article

Synthesis and biological activities of 3-aminoimidazo[1,2-α]pyridine compounds

Nawaf Al‐Maharik, Ismail Warad, Nisreen Al-Hajj, Yousef Salama et al.
BMC Chemistry
Synthesis and Reactivity of Heterocycles
article

Synthesis and biological activities of 3-aminoimidazo[1,2-α]pyridine compounds

Nawaf Al‐Maharik, Ismail Warad, Nisreen Al-Hajj, Yousef Salama, Rand Hazzam, Isra’ Al-Qadi, Michel Hanania, Saki Raheem
article en

Abstract

Despite their importance in cancer treatment, anticancer compounds face significant challenges due to drug resistance and low specificity, creating an urgent need for the discovery of more effective alternative. Herein, we report the synthesis of eleven 3-aminoimidazole[1,2-α]pyridine compounds (9-19) employing the one-pot Groebke-Blackburn-Bienayme three-component reaction (GBB-3CR). The cytotoxicity of the synthesised compounds was evaluated against three cancer cell lines (MCF-7, HT-29, B16F10) and a normal cell (MEF). Considering effectiveness and safety, the results demonstrated that among the eleven synthesised compounds, only compounds 12 and 14 exhibited high inhibitory activity against cancer cell lines. Compound 12 with a nitro group at the C-2 position and a p-chlorophenyl group at C-3 position, showed the highest inhibitory activity against HT-29, with an IC<sub>50</sub> of 4.15 ± 2.93 µM. Additionally, compound 14, with a tolyl moiety at the C-2 position and a p-chlorophenyl amine at C-3 position, can also be considered a promising bioactive product against B16F10, with an IC<sub>50</sub> of 21.75 ± 0.81 µM. Further research on these compounds may yield more potent candidates for the development of new anticancer agents.

BMC ChemistryVol. 19(1)
Bethlehem University (PS), An-Najah National University (PS), University of Westminster (GB)
Good health and well-being
Openalex Percentile: Top 97%
Synthesis and Reactivity of Heterocycles
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