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Molecules 2013, 18(11), 13385-13397; doi:10.3390/molecules181113385
Article

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

1
, 1
, 1
, 2,3
, 2,3
, 4
, 5
, 5
, 5
 and 1,*
Received: 29 August 2013; in revised form: 5 October 2013 / Accepted: 17 October 2013 / Published: 30 October 2013
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Abstract: 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.
Keywords: imidazole; [4,5-e][1,3]diazepine; anti-RSV; anti-tumor imidazole; [4,5-e][1,3]diazepine; anti-RSV; anti-tumor
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Wittine K, Poljak K, Kovač M, Makuc D, Plavec J, Balzarini J, Martinović T, Pavelić SK, 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(11):13385-13397.

Chicago/Turabian Style

Wittine, Karlo; Poljak, Kristina; Kovač, Matea; Makuc, Damjan; Plavec, Janez; Balzarini, Jan; Martinović, Tamara; Pavelić, Sandra K.; Pavelić, Krešimir; Mintas, Mladen. 2013. "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 18, no. 11: 13385-13397.


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