Abstract
The reactions of 2,4-bis(4-methoxyphenyl)-1,3-dithio-2,4-diphosphetane-2,4-disulfide (Lawesson’s Reagent, LR) with benzylamine (BzNH2) and 4-phenylbutylamine (PhBuNH2) yield benzylammonium P-(4-methoxyphenyl)-N-benzyl-amidodithiophosphonate (BzNH3)(BzNH-adtp) and 4-phenylbutylammonium P-(4-methoxyphenyl)-N-(4-phenylbutyl)-amidodithiophosphonate (PhBuNH3)(PhBuNH-adtp). The relevant nickel complexes [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] and the corresponding hydrolysed derivatives (BzNH3)2[Ni(dtp)2] and (PhBuNH3)2[Ni(dtp)2] were prepared and fully characterized. The antimicrobial activity of the aforementioned amidodithiophosphonates against a set of Gram-positive and Gram-negative pathogen bacteria was evaluated, and [Ni(BzNH-adtp)2] and [Ni(PhBuNH-adtp)2] showed antiproliferative activity towards Staphylococcus aureus and Staphylococcus haemolyticus strains. density functional theory (DFT) calculations were performed to shed some light on the activity of reported compounds related to their tendency towards P–N bond cleavage.
Highlights
Phosphorus-1,1-dithiolates such as dithiophosphates, dithiophosphinates, dithiophosphonates, and amidodithiophosphonates (I, II, III and IV, respectively, see Scheme 1), are important classes of sulfur-donor anionic ligands that display a multiplicity of coordination patterns with transition metal ions and main group elements [1,2,3]
The reaction between Lawesson’s Reagent (LR) and isopropylamine (i PrNH2 ), benzylamine (BzNH2 ), and 4-phenylbutylamine (PhBuNH2 ) in toluene gave rise to the corresponding amidodithiophosphonate ammonium salts (i PrNH3 )(i PrNH-adtp), (BzNH3 )(BzNH-adtp), and (PhBuNH3 )(PhBuNH-adtp) that were reacted with nickel chloride hexahydrate, yielding the corresponding amidodithiophosphonato complexes [Ni(i PrNH-adtp)2 ], [Ni(BzNH-adtp)2 ] and
All the compounds were tested against a library of bacteria and fungi of clinical importance belonging to the genera Staphylococcus, Escherichia, and Pseudomonas, and Candida, but only the complexes [Ni(BzNH-adtp)2 ] and [Ni(PhBuNH-adtp)2 ] demonstrated some antimicrobial activity that was tentatively ascribed to their tendency towards hydrolysis
Summary
Phosphorus-1,1-dithiolates such as dithiophosphates, dithiophosphinates, dithiophosphonates, and amidodithiophosphonates (I, II, III and IV, respectively, see Scheme 1), are important classes of sulfur-donor anionic ligands that display a multiplicity of coordination patterns with transition metal ions and main group elements [1,2,3]. The PS2 − moiety can coordinate in monodentate, bidentate (with either symmetric or asymmetric bonding), and polydentate modes. Since the early 1960s, dithiophosphates and dithiophosphinates gained increasing importance due to their applications as pesticides and extracting agents in mineral ores, and a large amount of information describing the reactivity of compounds I and II was reported [5]. Due to synthetic difficulties, the chemistry of dithiophosphonate. 2052 was reported [5]. Due to synthetic difficulties, the chemistry compounds compounds II and and II
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