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

• Published in: Molecules (Basel, Switzerland) Vol. 21; no. 7; p. 936
• Main Authors: Lewkowski, Jarosław, Rodriguez Moya, Maria, Chmielak, Marta, Rogacz, Diana, Lewicka, Kamila, Rychter, Piotr
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI 19.07.2016; MDPI AG
• Subjects: aminophosphonates; Animals; Crustacea - drug effects; ecotoxicity; Magnetic Resonance Spectroscopy; Organophosphonates - chemical synthesis; Organophosphonates - chemistry; Organophosphonates - toxicity; ostracode test; pyrene-1-carboxaldehyde; Pyrenes - chemistry; Toxicity Tests; Vibrio - drug effects; Vibrio fisheri test; pyrene-1-carboxaldehyde; ecotoxicity; ostracode test; Vibrio fisheri test; aminophosphonates
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules21070936

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.