title: Synthesis, Spectral Characterization of Several Novel Pyrene-Derived Aminophosphonates and Their Ecotoxicological Evaluation Using Heterocypris incongruens and Vibrio fisheri Tests.
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 3a-d 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 3a-d and 4, but no evident correlation between the structure and toxicity has been found.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of &#321;&#243;d&#378;, Tamka 12, 91-403 &#321;&#243;d&#378;, Poland. jlewkow@uni.lodz.pl.
authors.forename: Jarosław
authors.initials: J
authors.lastname: Lewkowski
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of &#321;&#243;d&#378;, Tamka 12, 91-403 &#321;&#243;d&#378;, Poland. MRM_chem@wp.pl.
authors.forename: Maria
authors.initials: M
authors.lastname: Rodriguez Moya
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of &#321;&#243;d&#378;, Tamka 12, 91-403 &#321;&#243;d&#378;, Poland. martachmielak1@gmail.com.
authors.forename: Marta
authors.initials: M
authors.lastname: Chmielak
authors.affiliation: Institute of Chemistry, Environmental Protection and Biotechnology, Jan D&#322;ugosz University in Częstochowa, 13/15 Armii Krajowej Av., 42-200 Częstochowa, Poland. diana.rogacz@gmail.com.
authors.forename: Diana
authors.initials: D
authors.lastname: Rogacz
authors.affiliation: Institute of Chemistry, Environmental Protection and Biotechnology, Jan D&#322;ugosz University in Częstochowa, 13/15 Armii Krajowej Av., 42-200 Częstochowa, Poland. lewickakamilla@gmail.com.
authors.forename: Kamila
authors.initials: K
authors.lastname: Lewicka
authors.affiliation: Institute of Chemistry, Environmental Protection and Biotechnology, Jan D&#322;ugosz University in Częstochowa, 13/15 Armii Krajowej Av., 42-200 Częstochowa, Poland. p.rychter@ajd.czest.pl.
authors.forename: Piotr
authors.initials: P
authors.lastname: Rychter
mesh_terms: D000818:Animals; D003445:Crustacea / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D011721:Pyrenes / Q000737:chemistry*; D018675:Toxicity Tests; D014733:Vibrio / Q000187:drug effects*
chemical_list: D063065:Organophosphonates; D011721:Pyrenes
keywords: Vibrio fisheri test; aminophosphonates; ecotoxicity; ostracode test; pyrene-1-carboxaldehyde