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Open AccessArticle

The Novel [4,5-e][1,3]Diazepine-4,8-dione and Acyclic Carbamoyl Imino-Ureido Derivatives of Imidazole: Synthesis, Anti-Viral and Anti-Tumor Activity Evaluations

Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, Zagreb HR-10000, Croatia
Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, P. O. B. 660, Ljubljana SI-1001, Slovenia
EN-FIST Centre of Excellence, Dunajska 156, Ljubljana SI-1001, Slovenia
Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium
Department of Biotechnology, University of Rijeka, Radmile Matejčić 2, Rijeka 51000, Croatia
Author to whom correspondence should be addressed.
Molecules 2013, 18(11), 13385-13397;
Received: 29 August 2013 / Revised: 5 October 2013 / Accepted: 17 October 2013 / Published: 30 October 2013
In the present paper, we report on the synthesis, and in vitro antiviral and cytostatic activities of a series of novel imidazole[4,5-e][1,3]diazepine-4,8-dione (compounds 911) and acyclic carbamoyl imino-ureido imidazole (compounds 12 and 13) derivatives. These new type of chemical entities showed no significant activity on the broad spectrum of DNA and RNA viruses. Results of antiproliferative assays performed on a panel of selected human tumor cell lines revealed that only compounds 1 and 5 showed moderate and selective cytostatic effect against HeLa cells (IC50 = 24 and 32 µM) with no concomitant cytotoxic effects on human normal fibroblasts (BJ). Importantly, an imidazole derivative containing a pyrrolidine moiety linked via an ethylenic spacer (3) showed a selective cytostatic effect toward cervical carcinoma (HeLa) cells (IC50 = 9.5 µM) with no apparent cytotoxicity on human normal fibroblasts (BJ). This compound can be therefore considered as a potential anti-tumor lead compound for further synthetic structure optimization. View Full-Text
Keywords: imidazole; [4,5-e][1,3]diazepine; anti-RSV; anti-tumor imidazole; [4,5-e][1,3]diazepine; anti-RSV; anti-tumor
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Wittine, K.; Poljak, K.; Kovač, M.; Makuc, D.; Plavec, J.; Balzarini, J.; Martinović, T.; Pavelić, S.K.; Pavelić, K.; Mintas, M. The Novel [4,5-e][1,3]Diazepine-4,8-dione and Acyclic Carbamoyl Imino-Ureido Derivatives of Imidazole: Synthesis, Anti-Viral and Anti-Tumor Activity Evaluations. Molecules 2013, 18, 13385-13397.

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