Synthesis and biological evaluation of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones as antitumoral agents

Ugo Chiacchio; Vincenzina Barbera; Roberta Bonfanti; Gian Luigi Broggini; Agata Campisi; Silvia Gazzola; Rosalba Parenti; Giovanni Romeo

doi:10.1016/j.bmc.2013.07.019

Synthesis and biological evaluation of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones as antitumoral agents

Bioorg Med Chem. 2013 Sep 15;21(18):5748-53. doi: 10.1016/j.bmc.2013.07.019. Epub 2013 Jul 18.

Authors

Ugo Chiacchio¹, Vincenzina Barbera, Roberta Bonfanti, Gian Luigi Broggini, Agata Campisi, Silvia Gazzola, Rosalba Parenti, Giovanni Romeo

Affiliation

¹ Dipartimento di Scienze del Farmaco, Università di Catania, Italy. uchiacchio@unict.it

PMID: 23916151
DOI: 10.1016/j.bmc.2013.07.019

Abstract

A series of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones has been synthesized by an intramolecular, palladium(II) catalyzed, aminooxygenation of alkenyl ureas, readily available from glycine allylamides as starting materials. Biological tests showed that the obtained compounds are endowed with an interesting antitumoral activity against two human thyroid cancer cell lines, namely FTC-133 and 8305C, by promoting the apoptotic pathway and DNA fragmentation.

Keywords: Bicyclic piperazinones; Caspase-3; Domino reaction; Palladium; Thyroid cancers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / toxicity
Apoptosis / drug effects
Caspase 3 / metabolism
Cell Line, Tumor
DNA Fragmentation / drug effects
Humans
Oxazoles / chemistry*
Pyrazines / chemical synthesis
Pyrazines / chemistry*
Pyrazines / toxicity
Structure-Activity Relationship

Substances

Antineoplastic Agents
Oxazoles
Pyrazines
Caspase 3