603-33-8Relevant academic research and scientific papers
Phenylbismuth bis(2,5-dimethylbenzenesulfonate): Structure and properties
Sharutin,Sharutina
, p. 1119 - 1122 (2014)
Phenylbismuth bis(2,5-dimethylbenzenesulfonate) (I), a coordination polymer in which a bis-muth atom has a distorted square pyramidal coordination to an axial carbon atom (Bi-C, 2.247(5) A?) and basal oxygen atoms (Bi-O, 2.390(9)-2.403(10) A?), has been synthesized by the reaction between triphenyl- bismuth and 2,5-dimethylbenzenesulfonic acid (1 : 2 mol/mol) in toluene and structurally characterized. Pentaphenylbismuth and pentaphenylantimony phenylate compound I to triphenylbismuth.
Oxidation of magnesium with diphenylbismuth and diphenylantimony chlorides in polar solvents
Maslennikov,Klement'eva,Losev, Ya. V.,Spirina,Maslennikov
, p. 1 - 4 (2006)
The intermediate and final products of the reactions of magnesium with diphenylantimony and diphenylbismuth chlorides were identified, and the formal kinetic relationships of the process were elucidated. The apparent equilibrium constants, enthalpies, and
Making Bispirin: Synthesis, structure and activity against Helicobacter pylori of bismuth(iii) acetylsalicylate
Andrews, Philip C.,Blair, Victoria L.,Ferrero, Richard L.,Junk, Peter C.,Kumar, Ish
, p. 2870 - 2872 (2013)
Reaction of Bi(OtBu)3 with aspirin (acetylsalicylic acid = aspH) in dry toluene results in the bismuth(iii) complex, [Bi(O 2C(C6H4)OAc)3]∞ 1 (O2C(C6H4)OAc = asp), minimum inhibitory concentration (MIC) against Helicobacter pylori ≥ 6.25 μg mL-1, while the inclusion of a stoichiometric equivalent of KOtBu leads to crystals of the bismuthate salt [KBi(O2C(C6H 4)OAc)4]∞ 2. The Royal Society of Chemistry 2013.
Reactivity of TerN(SiMe3)BiCl2 - Synthesis of an Aminobismuthenium Cation and TerN(SiMe3)Bi(N3)2
Bresien, Jonas,Hering-Junghans, Christian,Schulz, Axel,Thomas, Max,Villinger, Alexander
, p. 2571 - 2580 (2018)
The reaction of TerN(SiMe3)BiCl2 (1) (Ter = 2,6-bis(2,4,6-trimethylphenyl)phenyl) with Lewis acids such as GaCl3 and Ag[OTf] (OTf = OSO2CF3) was studied. While the reaction of 1 with GaCl3 led to decomposition into bismuth black, TerNH2·GaCl3, and [TerNH3][GaCl4], the reactions of 1 with 1 and 2 equiv of Ag[OTf] resulted in methyl/triflate exchange reactions affording TerN(SiMe2OTf)Bi(Me)Cl (2) and TerN(SiMe2OTf)Bi(Me)OTf (3). To circumvent the methyl/triflate exchange, the diiodide compound TerN(SiMe3)BiI2 (5) and the azide-substituted derivatives TerN(SiMe3)Bi(Cl)N3 (6) and TerN(SiMe3)Bi(N3)2 (7) were prepared, although it was not possible to isolate pure 7 because of small impurities of 6. All of the bismuth compounds (1-7) were characterized by single-crystal X-ray diffraction and NMR, IR, and Raman spectroscopy. According to quantum-chemical calculations, 3 can be regarded as a donor-stabilized aminobismuthenium cation with OTf- as the counterion. As expected for bismuth compounds with aromatic scaffolds, Bi···-arene interactions were observed. The influence of the substitution at the bismuth atom on the strength of this intramolecular interaction with the terphenyl moiety was studied by experimental (crystal structures) and theoretical methods. A correlation between the Lewis acidity (NBO charge) and the Bi···-arene distance could be established.
Bismuth(III) saccharinate and thiosaccharinate complexes and the effect of ligand substitution on their activity against helicobacter pylori
Andrews, Philip C.,Ferrero, Richard L.,Forsyth, Craig M.,Junk, Peter C.,MacLellan, Jonathan G.,Peiris, Roshani M.
, p. 6283 - 6291 (2011)
Five bismuth(III) saccharinate and thiosaccharinate complexes, [Ph 2Bi(sac)]∞1, [Bi(sac)3]n2, [Ph2Bi(tsac)]∞4, [PhBi(tsac)2] n5, [Bi(tsac)3]n6 (sacH = saccharin, tsacH = thiosaccharin), have been synthesized and fully characterized. The tendency for ligand redistribution in [Ph2Bi(sac)]∞ has been investigated in solution by NMR spectroscopy. The structures of [Ph 2Bi(sac)]∞1 and [Ph2Bi(tsac)] ∞4 have been confirmed by X-ray crystallography. In Ph 2Bi(sac) the sac ligand is bound to a four-coordinate bismuth center via its imino nitrogen atom with an accompanying long-range Bi-O interaction. However, in the structure of [Ph2Bi(tsac)]∞ the ligand is σ-bound through the exocyclic sulfur atom, giving a thiolate complex, confirming the more thiophilic nature of bismuth(III). Both complexes consist of polymeric chain structures with formally four-coordinated bismuth atoms. The complexes were assessed for their activity against H. pylori. The activity is both ligand dependent and sensitive to the degree of ligand substitution. The saccharinate complexes, 1 and 2, show activity comparable with standard tris-carboxylato bismuth(III) compounds, 6.25 μg/mL, while the activity of the thiolato complexes, 4-6, increases dramatically on increasing the number of thiolate groups from one to three (range 50-6.25 μg/mL). Saccharin, thiosaccharin, and BiPh3 were found to be inactive.
Zinc reaction with diphenylantimony and diphenylbismuth chlorides in aprotic solvents
Losev,Klement'eva,Maslennikov,Spirina
, p. 1581 - 1583 (2006)
Products of zinc oxidation with diphenylantimony and diphenylbismuth chlorides in aprotic solvents are established. The effective adsorption constants of the reagents on the metal surface and the rate constants and activation energies of the processes und
The Importance of Heterolepticity in Improving the Antibacterial Activity of Bismuth(III) Thiolates
Luqman, Ahmad,Blair, Victoria L.,Brammananth, Rajini,Crellin, Paul K.,Coppel, Ross L.,Andrews, Philip C.
, p. 2738 - 2749 (2016)
Five mixed thiolatobismuth(III) complexes [BiPh(5-MMTD)2{4-MMT(H)}] (1), [Bi(1-MMTZ)2{(PYM)(PYM(H))2}] (2), [Bi(MBT)2(5-MMTD)] (3), [Bi(4-BrMTD)3{2-MMI(H)}] (4) and [Bi(1-MMTZ)2{1-MMTZ(H)}(
Formation of bismuth(V) thiolates: Protolysis and oxidation of triphenylbismuth(III) with heterocyclic thiols
Luqman, Ahmad,Blair, Victoria L.,Bond, Alan M.,Andrews, Philip C.
, (2013)
Stressing bismuth: Two monophenyl tetrathiolato BiV complexes, [BiPh(SR)4], have been prepared upon treating BiPh3 in toluene/ethanol under reflux conditions with an excess of N-heterocyclic thiols (see scheme), indicating
Homoleptic and heteroleptic bismuth(III) thiazole-thiolates and the influence of ring substitution on their antibacterial and antileishmanial activity
Luqman, Ahmad,Blair, Victoria L.,Brammananth, Rajini,Crellin, Paul K.,Coppel, Ross L.,Kedzierski, Lukasz,Andrews, Philip C.
, p. 725 - 733 (2015)
Two new homo- and heteroleptic bismuth thiazole-thiolato complexes derived from 4-phenylthiazole-2-thiol MBT(H) have been synthesised and structurally characterised, [BiPh(MBT)2]2 and [Bi(MBT)3]2. Syntheses were achieved using BiPh3 or Bi(OtBu)3 in protolysis reactions with MBT(H), or by salt metathesis with BiCl3 or BiPhCl2 and the sodium thiolate, [NaMBT]. The complexes were obtained under both standard solvent-free and solvent-mediated conditions, and by microwave irradiation. The solid-state structures of [BiPh(MBT)2]2 and [Bi(MBT)3]2, were determined using single-crystal X-ray diffraction, showing them to be dimeric. The bactericidal properties of the complexes against Mycobacterium smegmatis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE) and Escherichia coli revealed [BiPh(MBT)2]2 to be the most effective against all the bacteria with MIC values of 0.6 μg/mL (0.25 μM) against S. aureus and 0.9 μg/mL (0.27 μM) against E. faecalis. [Bi(MBT)3]2 was less active overall. However, comparisons with the analogous complex [Bi(4-BrMTD)3], revealed a significant hundred-fold enhanced activity against S. aureus, MRSA, VRE, and E. faecalis. Both complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. [BiPh(MBT)2]2 also was found to display good antileishmanial activity with an IC50 value of 0.11 μg/mL (0.17 μM), at which concentration the complex was non-toxic to human fibroblast cells.
The thiol-based reduction of Bi(V) and Sb(V) anti-leishmanial complexes
Duffin, Rebekah N.,Stephens, Liam J.,Blair, Victoria L.,Kedzierski, Lukasz,Andrews, Philip C.
, (2021/05/10)
Low molecular weight thiols including trypanothione and glutathione play an important function in the cellular growth, maintenance and reduction of oxidative stress in Leishmania species. In particular, parasite specific trypanothione has been established as a prime target for new anti-leishmania drugs. Previous studies into the interaction of the front-line Sb(V) based anti-leishmanial drug meglumine antimoniate with glutathione, have demonstrated that a reduction pathway may be responsible for its effective and selective nature. The new suite of organometallic complexes, of general formula [MAr3(O2CR)2] (M = Sb or Bi) have been shown to have potential as new selective drug candidates. However, their behaviour towards the critical thiols glutathione and trypanothione is still largely unknown. Using NMR spectroscopy and mass spectrometry we have examined the interaction of the analogous Sb(V) and Bi(V) organometallic complexes, [SbPh3(O2CCH2(C6H4CH3))2] S1 and [BiPh3(O2CCH2(C6H4CH3))2] B1, with the trifluoroacetate (TFA) salt of trypanothione and L-glutathione. In the presence of trypanothione or glutathione at the clinically relevant pH of 4–5 for Leishmania amastigotes, both complexes undergo facile and rapid reduction, with no discernible difference. However, at a higher pH (6–7), the complexes behave quite differently towards glutathione. The Bi(V) complex is again reduced rapidly but the Sb(V) complex undergoes slow reduction over 8 h (t1/2 = 54 min.) These results give the first insights into why the highly oxidising Bi(V) complexes display low selectivity in their cytotoxicity towards leishmanial and mammalian cells, while the Sb(V) complexes show good selectivity.
