New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities
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ORIGINAL PAPER
New maleimide 1,2,3‑triazole hybrids: design, synthesis, anticancer, and antimicrobial activities Bader A. Salameh1 · Kayed A. Abu‑Safieh1 · Eman H. Al‑Hushki1 · Wamidh H. Talib2 · Israa A. Al‑ataby2 · Raed A. Al‑Qawasmeh3 Received: 4 June 2020 / Accepted: 7 September 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract A new series of maleimide triazole hybrid compounds namely 3-chloro-1-[(1-aryl-1H-1,2,3-triazol-4-yl)methyl]-4(arylamino)-1H-pyrrole-2,5-dione have been prepared. Our synthetic strategy starts via the reaction of 2,3-dichloromaleic anhydride with propargyl amine followed by chlorine displacement with arylamine and subsequent formation of a triazole utilizing copper(I) catalyzed azide-alkyne cycloaddition reaction, that generates the designed triazole nucleus. The produced hybrid compounds were identified using various physicochemical properties of the pure compounds. The synthesized compounds were screened for antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, and Bacillus spizizenii. While selected compounds were tested for their anticancer activities against T47D, HCT 116, and VERO cell lines. Graphic abstract
Keywords Alkynes · Antitumor agents · Heterocycles · Triazole · Maleimide
Introduction Cancer is a disease that poses a serious threat to human life, it was considered as the second leading cause of death in many countries [1], and became, over the years, one of the Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02685-4) contains supplementary material, which is available to authorized users. * Bader A. Salameh [email protected] 1
Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa 13133, Jordan
2
Department of Clinical Pharmacy and Therapeutics, Applied Science Private University, Amman 11931, Jordan
3
Department of Chemistry, Faculty of Sciences, University of Sharjah, 27272 Sharjah, UAE
major challenges that facing the health and scientific community. The enormous efforts that were directed to overcome this disease led up to a globally increasing demand for new anticancer drugs. Chemical synthesis is one of the major research areas that provide the world with new anticancer compounds. One of the promising classes of these compounds is the maleimides [1–11]. Maleimides have received little attention [12] despite its promising activities, they are being considered as bioactive compounds [13] due to the biological activity of their derivatives which include but not limited to anticancer [1–3, 11, 14], anti-bacterial [2, 15, 16], and anti-fungal activities [17] (Fig. 1). On the other hand, the chemistry of the triazole has been developed a lot recently. Since 2002, the copper-catalyzed azide-alkyne cycloaddition reaction (CuAAC) [18, 19], which widely known as one of the most common click chemistry reactions, has rapidly spread into medicinal chemistry field [20, 21].
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