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Synthesis and antiproliferative activity evaluation of imidazole-based indeno[1,2-b]quinoline-9,11-dione derivatives

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Abstract

A series of new imidazole substituted indeno[1,2-b]quinoline-9,11-dione derivatives were synthesized and evaluated for their antiproliferative effects on HeLa, LS180, MCF-7 and Jurkat human cancer cell lines. Antiproliferative effects were evaluated using MTT assay. Prepared compounds exhibited weak to good antiproliferative activity in evaluated cell lines. Prepared compounds were more potent in Jurkat cell line when compared to LS180, HeLa and MCF-7 cell lines. Compounds 29 (IC16 = 0.7 μM) and 31 (IC16 = 1.7 μM) and 33 (IC16 = 1.7 μM) were found to be the most potent molecules on Jurkat cell lines. Moreover; it was found that some of the tested compounds bearing imidazole-2-yl moiety on the C11-position of dihydropyridine ring exhibited superior antiproliferative activity in comparison to cis-platin especially in Jurkat cell line (compounds 29, 31, and 33). It seemed that the introduction of electron-withdrawing groups on the imidazole ring enhanced the antiproliferative potential of these compounds (compounds 27, 29 and 31). The results of this study proposed that some of the imidazole substituted indeno[1,2-b]quinoline-9,11-dione compounds may act as efficient anticancer agents in vitro, emphasizing their potential role as a source for rational design of potent antiproliferative agents.

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Acknowledgments

This work was financially supported by research council of Shiraz University of Medical Sciences and Tehran University of Medical Sciences.

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Authors and Affiliations

  1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, 14176, Tehran, Iran

    Hasti Sarkarzadeh, Mohsen Amini, Najmeh Edraki & Abbas Shafiee

  2. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, PO Box 3388-71345, 71345, Shiraz, Iran

    Ramin Miri, Omidreza Firuzi, Nima Razzaghi-Asl & Najmeh Edraki

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  1. Hasti Sarkarzadeh
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Correspondence to Ramin Miri or Abbas Shafiee.

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Sarkarzadeh, H., Miri, R., Firuzi, O. et al. Synthesis and antiproliferative activity evaluation of imidazole-based indeno[1,2-b]quinoline-9,11-dione derivatives. Arch. Pharm. Res. 36, 436–447 (2013). https://doi.org/10.1007/s12272-013-0032-7

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