Year : 2021  |  Volume : 20  |  Issue : 4  |  Page : 303-312

Synthesis, characterization, anticancer activity, and molecular docking of novel maleimide–succinimide derivatives

Department of Chemistry, College of Education for Pure Sciences, University of Basrah, Basrah, Iraq

Correspondence Address:
PhD Ali A.A Al-Shawi
Department of Chemistry, College of Education for Pure Sciences, University of Basrah, Basrah (Zip Code 61)
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Source of Support: None, Conflict of Interest: None

DOI: 10.4103/epj.epj_26_21

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Background and objective A wide range of maleimide heterobifunctional reagents are used for the preparation of targeted therapeutics. Succinimide derivatives are important compounds found in a variety of natural products that exhibit remarkable biological and pharmaceutical activity. The creation of new maleimide–succinimide derivatives will increase the importance and medicinal applications of these groups. Materials and methods The reaction of bismaleimide (1–2) with phenylhydrazide and 4-methylbenzohydrazide resulted in the formation of N’-[1-(4-[2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl] phenyl)-2,5-dioxopyrrolidin-3-yl] benzohydrazide (3), N’-[1-(4-[2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl] phenyl)-2,5-dioxopyrrolidin-3-yl]-4-methylbenzohydrazide (4), N’-[1-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-[1,1’-biphenyl]-4-yl)-2,5-dioxopyrrolidin-3-yl] benzohydrazide (5), and N-[1-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-[1,1’- biphenyl]-4-yl)-2,5-dioxopyrrolidin-3-yl]-4-methylbenzohydrazide (6). The interaction of potential compounds with AKT1 and CDK2 proteins was performed using molecular docking to target the hydrogen bond and amino acid residues. Results The new compounds were characterized using Fourier-transform infrared spectroscopy,1H-NMR,13C-NMR spectroscopy, and mass spectrometry. The MTT assay was used to test cell viability against breast cancer cells (MCF-7). The cytotoxicity results revealed that compounds 3 and 5 were more toxic than compounds 4 and 6. Molecular docking of compounds that interacted with AKT1 and CDK2 showed affinity energy of −16.112 and −21.342 kcal/mol for compound 3, while −22.398 and −19.940 kcal/mol for compound 5. The root-mean-square deviation values for CDK2 and AKT1 were 2.27 and 1.61 for compound 3, respectively, and 1.93 and 1.90 for compound 5. Conclusion Toxicity and molecular docking studies revealed that compounds 3 and 5 could be developed as anticancer agents against breast cancer, indicating that further research is warranted.

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