- Bismuth(iii) Thiophosphinates: Understanding How a Small Atomic Change Influences Antibacterial Activity and Mammalian Cell Viability
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Diphenylphosphinothioic acid (HSP(=O)Ph2) and diphenylphosphinodithioic acid (HSP(=S)Ph2) have been used to synthesise four BiIII complexes: 1 [Bi(SP(=O)Ph2)3], 2 [BiPh(SP(=O)Ph2)2], 3 [BiPh2(SP(=O)Ph2)], and 4 [Bi(SP(=S)Ph2)3], using BiPh3 and [Bi(OtBu)3] as bismuth sources. The complexes have been characterised by NMR spectroscopy, mass spectrometry, infrared spectroscopy, powder X-ray diffraction, and singe crystal X-ray crystallography (2-4). Biological studies indicated that despite complexes 2 and 3 reducing mammalian cell viability, their antibacterial activity provides a good degree of selectivity towards both Gram positive and Gram negative bacterial strains. The minimum inhibitory concentrations for complexes 2 and 3 are in the range of 0.52-5.5 μM towards the bacteria tested. Homoleptic complexes 1 and 4 were generally less active towards both bacterial and mammalian cells.
- Senevirathna, Dimuthu C.,Duffin, Rebekah N.,Stephens, Liam J.,Herdman, Megan E.,Werrett, Melissa V.,Andrews, Philip C.
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p. 1226 - 1236
(2020/10/07)
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- N-(diphenylphosphinothioyl)hydroxylamine: Preparation, characterisation and base-induced transposition of sulfur and oxygen atoms in its O-benzoyl derivative
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N-(Diphenylphosphinothioyl)hydroxylamine 5 has been prepared from Ph2P(S)Cl using H2NOSiMe3 and has been converted into its O-benzoyl derivative Ph2P(S)NHOCOPh 6. The principal reaction of the derivative 6 with base (NaOMe or ButNH2) is rearrangement, transposition of sulfur and oxygen giving Ph2P(O)NHSCOPh 7; this then reacts further, forming the phosphinic amide Ph2P(O)NH2 together with PhCO2Me or PhCONHBut. The rearrangement probably involves intramolecular nucleophilic displacement of benzoate by the P=S group of 6, forming an intermediate with P, N and S atoms in a three-membered ring.
- Harger, Martin J. P.
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p. 3205 - 3209
(2007/10/03)
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- Acylation of Phosphorus-Substituted CH Acids under the Conditions of Phase-transfer Catalysis III. Acylation of Thiophosphinoylacetonitriles
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Acylation of thiophosphinoylacetonitriles under the conditions of phase-transfer catalysis involves the central carbon atom with formation of C-acyl derivatives in the enol form (Z-isomers) stabilized by intramolecular hydrogen bonding. Acylation with aromatic acyl halides also gives products of double C,O-acylation (Z-isomers), often predominating in amount. The yield of acylation products is affected by substituents at the phosphorus atom, the nature of acylating agent, and reaction conditions. The data of X-ray structural investigations of single crystals of (diphenylthiophosphinoyl)acetylacetonitrile enol and [isobutoxy(methyl)thiophosphinoylbenzoylacetonitrile enol benzoate are presented.
- Odinets,Artyushin,Kalyanova,Petrovskii,Lysenko,Antipin,Struchkov,Mastryukova,Kabachnik
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- The reaction of α-amino-substituted diphenylphosphine oxide anions with elemental sulfur and selenium. A new route to thio- and selenoamides
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The lithiated anions of α-amino-substituted diphenylphosphine oxides 1, in which R can be hydrogen, aryl, alkyl and alkenyl, react with two equivalents of sulfur or selenium to form thio- and selenoamides, which can be isolated in good to excellent yields
- Otten, P. A.,Gen, A. van der
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p. 499 - 506
(2007/10/02)
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- OPTICALLY ACTIVE SILYL ESTERS OF PHOSPHOROUS. II. STEREOCHEMISTRY OF REACTIONS WITH NUCLEOPHILES
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We report the stereochemistry of reactions of various nucleophiles with optically active silyl esters of phosphorus of general formula: tBuPhP(X)OSiMePhNp X= -(1), Oxygen (2), Sulfur (3), Selenium (4).The list of nucleophiles includes O,S,N,C nucleophiles as well as halides.The nucleophilic attack is essentially directed towards silicon.The phosphinuos and phosphonic acid esters react with predominant retention of configuration at silicon atom, whereas the thiono and seleno crossover is explained in terms of possible interaction of the electrophilic part of the nucleophile with the oxyphosphoryl group or tricoordinate phosphorous.
- Wozniak, Lucyna,Cypryk, Marek,Chojnowski, Julian
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p. 4403 - 4414
(2007/10/02)
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- Preparation of β-Substituted trans-Ethylene Diphenylphosphines and Sulphides by P(O) and P(S)-activated Olefination
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Methylene bis-diphenylphosphine monoxide (3c) in toluene reacts regiospecifically and stereoselectively with aldehydes in the presence of potassium tert-butoxide to β-substituted trans-ethylene diphenylphosphines 6, which can be oxidized to the sulphides 2 by sulphur in acetone.These sulphides 2 are to be obtained also directly from methylene bis-diphenylphosphine oxide sulphide 3b and methylene bis-diphenylphosphine disulphide 3d, respectively, under the same olefination conditions.But the yields are smaller and the purification of the raw products is much more difficult, if 3d is used.
- Gloyna, Dieter
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p. 360 - 366
(2007/10/02)
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