“…Organophosphorus–fluorine compounds (OPFCs) bearing P–F bonds have been of considerable interest since the 1970s due to their diverse chemical and biological activities. They are an important class of organophosphorus compounds and are recognized as selective phosphorylating agents in synthesis, and efficient inhibitors of several classes of enzymes. − The thiophosphate anions A – C (Scheme ) were first prepared from the reaction of alkali metal fluorides and P 4 S 10 by Roesky and co-workers. , Since then, the synthesis of thiophosphoryl halides SPF 3 and SPFCl 2 , and their derivatives SPF 2 NH 2 , SPFClNH 2 , SPF 2 NPF 2 X (X = Br, NH 2 or OH), SPF 2 NPCl 3 , and SPF 2 NPF 2 NCNSiMe 3 , was reported. − However, there are few examples of the synthesis of simple phosphonofluorodithioates ROP(S)(S – )F containing a fluorine atom attached directly to the phosphorus atom. ,, The nucleoside phosphonofluoridodithioate monoesters were prepared via oxidation of nucleoside phosphonodithioate with I 2 in pyridine in the presence of TMSCl, followed by addition of triethylamine trishydrofluoride (TAF). , Similar analogues were obtained from a one-pot sequential reaction of 1,3,2-dithiaphospholane P(III) derivatives, which were converted readily into the corresponding P(V) compounds by addition of elemental sulfur and finally into phosphonofluoridodithioates by further treatment with TBAF . The importance of phosphoro-fluorine compounds in pure and applied chemistry invigorated our interest in synthesizing new phosphorodiselenoates bearing the P–F motif. 1 Fluorinated Thiophosphate Anions A – C …”
2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, [PhP(Se)(μ-Se)]2, Woollins' reagent (WR), reacts with dry KF or tetrabutylammonium fluoride (TBAF) at room temperature generating the corresponding potassium and tetrabutylammonium phenyldiselenofluorophosphinates 1 and 2 in almost quantitative yields. Treating 1 with equimolar amounts of tetraphenylphosphonium chloride or 1,3-dimesityl-1H-imidazol-3-ium chloride in THF at room temperature afforded the corresponding organic adducts 3 and 4 in 90% and 87% yields. Reaction of 1 with mono- and dihalogenated alkanes gave a series of esters of phenylphosphonofluoridodiselenoates 5-8 and 9 in 79-93% yields. Two representative crystal structures are reported.
“…Organophosphorus–fluorine compounds (OPFCs) bearing P–F bonds have been of considerable interest since the 1970s due to their diverse chemical and biological activities. They are an important class of organophosphorus compounds and are recognized as selective phosphorylating agents in synthesis, and efficient inhibitors of several classes of enzymes. − The thiophosphate anions A – C (Scheme ) were first prepared from the reaction of alkali metal fluorides and P 4 S 10 by Roesky and co-workers. , Since then, the synthesis of thiophosphoryl halides SPF 3 and SPFCl 2 , and their derivatives SPF 2 NH 2 , SPFClNH 2 , SPF 2 NPF 2 X (X = Br, NH 2 or OH), SPF 2 NPCl 3 , and SPF 2 NPF 2 NCNSiMe 3 , was reported. − However, there are few examples of the synthesis of simple phosphonofluorodithioates ROP(S)(S – )F containing a fluorine atom attached directly to the phosphorus atom. ,, The nucleoside phosphonofluoridodithioate monoesters were prepared via oxidation of nucleoside phosphonodithioate with I 2 in pyridine in the presence of TMSCl, followed by addition of triethylamine trishydrofluoride (TAF). , Similar analogues were obtained from a one-pot sequential reaction of 1,3,2-dithiaphospholane P(III) derivatives, which were converted readily into the corresponding P(V) compounds by addition of elemental sulfur and finally into phosphonofluoridodithioates by further treatment with TBAF . The importance of phosphoro-fluorine compounds in pure and applied chemistry invigorated our interest in synthesizing new phosphorodiselenoates bearing the P–F motif. 1 Fluorinated Thiophosphate Anions A – C …”
2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, [PhP(Se)(μ-Se)]2, Woollins' reagent (WR), reacts with dry KF or tetrabutylammonium fluoride (TBAF) at room temperature generating the corresponding potassium and tetrabutylammonium phenyldiselenofluorophosphinates 1 and 2 in almost quantitative yields. Treating 1 with equimolar amounts of tetraphenylphosphonium chloride or 1,3-dimesityl-1H-imidazol-3-ium chloride in THF at room temperature afforded the corresponding organic adducts 3 and 4 in 90% and 87% yields. Reaction of 1 with mono- and dihalogenated alkanes gave a series of esters of phenylphosphonofluoridodiselenoates 5-8 and 9 in 79-93% yields. Two representative crystal structures are reported.
“…Finally, the solid residue was dried under vacuum to obtain the desired bisquaternary pyridinium compounds 39 – 46 in 60–80% yield. Compounds 39 – 41 and 44 were characterized by comparison of their spectral data with literature values 26, 27, 30…”
Oxime reactivators are the drugs of choice for the post-treatment of OP (organophosphorus) intoxication and used widely for mechanistic and kinetic studies of OP-inhibited cholinesterases. The purpose of the present study was to evaluate new oxime compounds to reactivate acetylcholinesterase (AChE) inhibited by the OP paraoxon. Several new bisquaternary pyridinium oximes with heterocyclic linkers along with some known bisquaternary pyridinium oximes bearing aliphatic linkers were synthesized and evaluated for their in vitro reactivation potency against paraoxon-inhibited electric eel acetylcholinesterase (EeAChE) and recombinant human acetylcholinesterase (rHuAChE). Results herein indicate that most of the compounds are better reactivators of EeAChE than of rHuAChE. The reactivation potency of two different classes of compounds with varying linker chains was compared and observed that the structure of the connecting chain is an important factor for the activity of the reactivators. At a higher concentration (10 −3 M), compounds bearing aliphatic linker showed better reactivation than compounds with heterocyclic linkers. Interestingly, oximes with a heterocyclic linker inhibited AChE at higher concentration (10 −3 M), whereas their ability to reactivate was increased at lower concentrations (10 −4 M and 10 −5 M). Compounds bearing either a thiophene linker 26, 46 or a furan linker 31 showed 59%, 49% and 52% reactivation of EeAChE, respectively, at 10 −5 M. These compounds showed 14%, 6% and 15% reactivation of rHuAChE at 10 −4 M. Amongst newly synthesized analogs with heterocyclic linkers (26-35 and 45-46), compound 31, bearing furan linker chain, was found to be the most effective reactivator with a k r 0.042 min −1 , which is better than obidoxime (3) for paraoxoninhibited EeAChE. Compound 31 showed a k r 0.0041 min −1 that is near equal to pralidoxime (1) for paraoxon-inhibited rHuAChE.
“…4PCB was synthesised by the reaction between 4-pyridoxime (2.03 mmol, 250 mg) in dried acetone and 4-(bromo methyl) phenyl acetic acid (3.65 mmol, 1.680 g). 22 Reaction mixture was stirred at reuxing for 28 h aer that precipitates appeared in the reaction mixture. It was ltered and solvent was evaporated under vacuum on rota evaporator.…”
Section: Synthesis Of 1-(4-carboxymethyl-benzyl)-4-(hydroxyimino-meth...mentioning
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