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Volume 19
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10.3390/molecules19044814
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Article

Exploring the Phe-Gly Dipeptide-Derived Piperazinone Scaffold in the Search for Antagonists of the Thrombin Receptor PAR1

by
Ángel M. Valdivielso
,
M. Teresa García-López
,
Marta Gutiérrez-Rodríguez
and
Rosario Herranz
*
Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
*
Author to whom correspondence should be addressed.
Molecules 2014, 19(4), 4814-4846; https://doi.org/10.3390/molecules19044814
Submission received: 4 February 2014 / Revised: 8 April 2014 / Accepted: 13 April 2014 / Published: 16 April 2014
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Abstract

A series of Phe-Gly dipeptide-derived piperazinones containing an aromatic urea moiety and a basic amino acid has been synthesized and evaluated as inhibitors of human platelet aggregation induced by the PAR1 agonist SFLLRN and as cytotoxic agents in human cancer cells. The synthetic strategy involves coupling of a protected basic amino acid benzyl amide to 1,2- and 1,2,4-substituted-piperazinone derivatives, through a carbonylmethyl group at the N1-position, followed by formation of an aromatic urea at the exocyclic moiety linked at the C2 position of the piperazine ring and removal of protecting groups. None of the compounds showed activity in the biological evaluation.
Keywords: peptidomimetics; regioselectivity; piperazinones; platelet antiaggregant activity; PAR1 antagonists peptidomimetics; regioselectivity; piperazinones; platelet antiaggregant activity; PAR1 antagonists
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MDPI and ACS Style

Valdivielso, Á.M.; García-López, M.T.; Gutiérrez-Rodríguez, M.; Herranz, R. Exploring the Phe-Gly Dipeptide-Derived Piperazinone Scaffold in the Search for Antagonists of the Thrombin Receptor PAR1. Molecules 2014, 19, 4814-4846. https://doi.org/10.3390/molecules19044814

AMA Style

Valdivielso ÁM, García-López MT, Gutiérrez-Rodríguez M, Herranz R. Exploring the Phe-Gly Dipeptide-Derived Piperazinone Scaffold in the Search for Antagonists of the Thrombin Receptor PAR1. Molecules. 2014; 19(4):4814-4846. https://doi.org/10.3390/molecules19044814

Chicago/Turabian Style

Valdivielso, Ángel M., M. Teresa García-López, Marta Gutiérrez-Rodríguez, and Rosario Herranz. 2014. "Exploring the Phe-Gly Dipeptide-Derived Piperazinone Scaffold in the Search for Antagonists of the Thrombin Receptor PAR1" Molecules 19, no. 4: 4814-4846. https://doi.org/10.3390/molecules19044814

APA Style

Valdivielso, Á. M., García-López, M. T., Gutiérrez-Rodríguez, M., & Herranz, R. (2014). Exploring the Phe-Gly Dipeptide-Derived Piperazinone Scaffold in the Search for Antagonists of the Thrombin Receptor PAR1. Molecules, 19(4), 4814-4846. https://doi.org/10.3390/molecules19044814

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