Synthesis and Evaluation of in Vitro Biological Activity of 4-Substituted Arylpiperazine Derivatives of 1,7,8,9-Tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

doi:10.3390/molecules14125189

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Molecules 2009, 14(12), 5189-5202; doi:10.3390/molecules14125189

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Synthesis and Evaluation of in Vitro Biological Activity of 4-Substituted Arylpiperazine Derivatives of 1,7,8,9-Tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Jerzy Kossakowski¹, Magdalena Pakosinska-Parys¹, Marta Struga^1,* , Izabela Dybala², Anna E. Koziol², Paolo La Colla^3,* , Laura Ester Marongiu³, Cristina Ibba³, David Collu³ and Roberta Loddo³

¹ Department of Medical Chemistry, Medical University, 3 Oczki Str., 02-007 Warsaw, Poland ² Faculty of Chemistry, Maria Curie-Sklodowska University, 20-031 Lublin, Poland ³ Department of Biomedical Science and Technology, University of Cagliari, Cittadella Universitaria, 09042, Monserrato, Cagliari, Italy

* Authors to whom correspondence should be addressed.

Received: 5 November 2009; in revised form: 26 November 2009 / Accepted: 1 December 2009 / Published: 11 December 2009

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Abstract: A series of twenty arylpiperazine derivatives of 1,7,8,9-tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione have been prepared. These derivatives were tested in vitro with the aim of identifying novel lead compounds active against emergent and re-emergent human and cattle infectious diseases (AIDS, hepatitis B and C, tuberculosis, bovine viral diarrhea). In particular, these compounds were evaluated in vitro against representatives of different virus classes, such as a HIV-1 (Retrovirus), a HBV (Hepadnavirus) and the single-stranded RNA⁺ viruses Yellow fever virus (YFV) and Bovine viral diarrhea virus (BVDV), both belonging to the Flaviridae. Compounds 2c, 2g and 3d showed a modest activity against CVB-2. The molecular structures of the starting imide 1 and one of propyl-piperazine derivatives, 3b, have been determined by an X-ray crystallography study.

Keywords: 1,7,8,9-tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione; arylpiperazine derivatives; X-ray crystal structure analysis; antiviral activity

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Cite This Article

MDPI and ACS Style

Kossakowski, J.; Pakosinska-Parys, M.; Struga, M.; Dybala, I.; Koziol, A.E.; La Colla, P.; Marongiu, L.E.; Ibba, C.; Collu, D.; Loddo, R. Synthesis and Evaluation of in Vitro Biological Activity of 4-Substituted Arylpiperazine Derivatives of 1,7,8,9-Tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione. Molecules 2009, 14, 5189-5202.

AMA Style

Kossakowski J., Pakosinska-Parys M., Struga M., Dybala I., Koziol A.E., La Colla P., Marongiu L.E., Ibba C., Collu D., Loddo R. Synthesis and Evaluation of in Vitro Biological Activity of 4-Substituted Arylpiperazine Derivatives of 1,7,8,9-Tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione. Molecules. 2009; 14(12):5189-5202.

Chicago/Turabian Style

Kossakowski, Jerzy; Pakosinska-Parys, Magdalena; Struga, Marta; Dybala, Izabela; Koziol, Anna E.; La Colla, Paolo; Marongiu, Laura Ester; Ibba, Cristina; Collu, David; Loddo, Roberta. 2009. "Synthesis and Evaluation of in Vitro Biological Activity of 4-Substituted Arylpiperazine Derivatives of 1,7,8,9-Tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione." Molecules 14, no. 12: 5189-5202.

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