New N-acyl- as well as N-phosphonoylmethyl- and N-phosphinoylmethyl-α-amino-benzylphosphonates by acylation and a tandem Kabachnik–Fields protocol

Abstract

Diethyl alfa-benzylamino- and alfa-amino-benzylphosphonates obtained by the Kabachnik–Fields reaction were useful intermediates in the synthesis of other derivatives. Acylation of the alfa-aminophosphonates with acyl chlorides led to the corresponding N-acyl...

Self-crosslinked polyvinyl alcohol/cellulose nanofibril cryogels loaded with synthesized aminophosphonates as antimicrobial wound dressings

“…44 Four different aldehydes were utilized in the synthesis process, along with the following amine; 4-(4-chlorophenyl)thiazol-2-amine (Scheme 1). Some techniques (IR, 1 H-NMR, 13 C-NMR, 31 P-NMR and Mass spectrometry) were used to interpret and investigate the chemical structures of the prepared a-aminophosphonate molecules (5)(6)(7)(8).…”

“…3,4 Amongst many others, a-aminophosphonate compounds were marked as potent pharmacophores from a drug-design perspective and showed promising biological activity against microbes and exhibited negligible toxicity toward mammalian cells. [5][6][7][8] The dressing materials should have characteristic features such as being biocompatible, biodegradable, easily produced and able to successfully restore their activity until reaching the target sites. Moreover, they should maintain a moist environment around the wound to enhance healing, 9 enable continuous wound site monitoring, allow the exchange of gases, and prevent subsequent infection of the wound and they should have a wide range spectrum of antimicrobial activity.…”

“…3,4 Amongst many others, α-aminophosphonate compounds were marked as potent pharmacophores from a drug-design perspective and showed promising biological activity against microbes and exhibited negligible toxicity toward mammalian cells. 5–8…”

Applying Heterogeneous Catalytic Reactions for Organic Chemical Syntheses

“…To obtain the key intermediate for these syntheses, (N-benzylaminomethyl)diphenylphosphine oxide (20) was debenzylated over a 10% Pd/C catalyst (Selcat Q), in methanol, at 12 bar and 75 °C to afford (aminomethyl)diphenylphosphine oxide (21) in 47% isolated yield (Scheme 12). Later, a similar Pd-catalyzed N-debenzylation was accomplished to obtain a diethyl (aminomethyl)phosphonate derivative [36].…”

N-Functionalization of β-aminophosphonates: cytotoxic effects of the new derivatives

“…36,37 Recently, our group has described tandem Kabachnik-Fields reactions with the intermediacy of α-amino-methylphosphonate derivatives, and the latter species were also modified by N-acylation. 38 Bioactivity studies including tests on different tumor cell lines revealed that the new α-aminophosphonic derivatives obtained by a second phospha-Mannich reaction or acylation showed more significant cytotoxic effects 39 than the starting α-aminophosphonates themselves. 40 In order to synthesize new aminophosphonic derivatives with potential biological activity, we wished to study the Kabachnik-Fields condensation and the acylation of β-aminophosphonates.…”