Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

Abstract

SummaryA large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20–97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivatives are stronger emissive compounds than the corresponding N-aryl derivatives. N-Benzylamino(pyren-1-yl)methylphosphonic acid displayed strong fluorescence (ΦF = 0.68) in phosphate-buffered saline (PBS). The influence of a series of derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC50 = 20.8 μM), simultaneously showing weak toxicity towards normal lymphocytes (IC50 = 230.8 µM).

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

“…This procedure gave imines 1a – e , which were isolated and used for further conversions without any purification. 1 H-NMR spectra were recorded only to verify the identity, based on the diagnostic 1 H-NMR singlet corresponding to the proton of the azomethine group (–CH=N–) above 8 ppm [17].…”

“…We have tried to fill this void and very recently have published results of our studies on the synthesis, photophysical properties and cytotoxic action of a series of α-aminophosphonates bearing pyren-1-yl moieties [17]. They demonstrated moderate-to-satisfactory cytotoxicities against two colon cancer cell lines.…”

6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction

“…The reaction of 3-methylaniline or tert-butylamine with pyrene-1-carboxaldehyde and dimethyl phosphite was also described in the presence of a catalytic amount of TFA ( Figure 6.5) [38]. The pyrene-derived α-aminophosphonates obtained showed fluorescent properties.…”

Advances in polymer precursors and bio‐based polymers synthesized from 5‐hydroxymethylfurfural

“…62,63 Diesters (13) have been synthesized via the esterification of (12) with corresponding alcohols. 64,65 Direct oxidative esterification of HMF to dimethyl 2,5-furandicarboxylate (13, R 5 methyl) was achieved using Au-ZrO 2 and Au-CeO 2 catalysts, respectively. [66][67][68] These monomers are valuable polyester precursors.…”