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Molecules 2016, 21(7), 936; doi:10.3390/molecules21070936

Synthesis, Spectral Characterization of Several Novel Pyrene-Derived Aminophosphonates and Their Ecotoxicological Evaluation Using Heterocypris incongruens and Vibrio fisheri Tests

1
Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
2
Institute of Chemistry, Environmental Protection and Biotechnology, Jan Długosz University in Częstochowa, 13/15 Armii Krajowej Av., 42-200 Częstochowa, Poland
M.Sc. student at the Faculty of Chemistry, University of Łódź (Academic Year 2015–2016).
*
Authors to whom correspondence should be addressed.
Academic Editor: György Keglevich
Received: 26 June 2016 / Revised: 12 July 2016 / Accepted: 14 July 2016 / Published: 19 July 2016
(This article belongs to the Special Issue Recent Advances in Organophosphorus Chemistry)
View Full-Text   |   Download PDF [863 KB, uploaded 19 July 2016]   |  

Abstract

Four diphenyl pyrene-derived aminophosphonates were synthesized. Attempts were made to synthesize diphenyl N-(R)-α-methylbenzylamino(pyren-1-yl)methylphosphonate (3e) in order to obtain the chiral aminophosphonate bearing a pyrene moiety. Because these attempts failed, dimethyl and dibenzyl N-(R)-α-methylbenzyl substituted aminophosphonates 4 and 5 were synthesized and the predominant diastereoisomer of dimethyl aminophosphonate 4 was isolated. The resolution of the diastereomeric mixture of 5 failed. Aminophosphonates 3ad and the predominant diastereoisomer of 4 were investigated in terms of their ecotoxicity using tests performed on the ostracode Heterocypris incongruens and the fluorescent bacterium Vibrio fisheri. The tests confirmed the moderate-to-high ecotoxicity of aminophosphonates 3ad and 4, but no evident correlation between the structure and toxicity has been found. View Full-Text
Keywords: pyrene-1-carboxaldehyde; aminophosphonates; ecotoxicity; ostracode test; Vibrio fisheri test pyrene-1-carboxaldehyde; aminophosphonates; ecotoxicity; ostracode test; Vibrio fisheri test
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MDPI and ACS Style

Lewkowski, J.; Rodriguez Moya, M.; Chmielak, M.; Rogacz, D.; Lewicka, K.; Rychter, P. Synthesis, Spectral Characterization of Several Novel Pyrene-Derived Aminophosphonates and Their Ecotoxicological Evaluation Using Heterocypris incongruens and Vibrio fisheri Tests. Molecules 2016, 21, 936.

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