5153-28-6Relevant academic research and scientific papers
Activity of antifungal organobismuth(III) compounds derived from alkyl aryl Ketones against S. cerevisiae: Comparison with a heterocyclic bismuth scaffold consisting of a diphenyl sulfone
Murafuji, Toshihiro,Tomura, Mai,Ishiguro, Katsuya,Miyakawa, Isamu
, p. 11077 - 11095 (2014/10/15)
A series of hypervalent organobismuth(III) compounds derived from alkyl aryl ketones [XBi(5-R′C6H3-2-COR)(Ar)] was synthesized to investigate the effect of the compounds' structural features on their antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to bismuth heterocycles [XBi(5-RC6H3-2-SO 2C6H4-1′-)] derived from diphenyl sulfones, a systematic quantitative structure-activity relationship study was possible. The activity depended on the Ar group and increased for heavier X atoms, whereas lengthening the alkyl chain (R) or introducing a substituent (R′) reduced the activity. IBi(C6H4-2-COCH 3)(4-FC6H4) was the most active. Its activity was superior to that of the related acyclic analogues ClBi[C6H 4-2-CH2N(CH3)2](Ar) and ClBi(C 6H4-2-SO2 tert-Bu)(Ar) and also comparable to that of heterocyclic ClBi(C6H4-2-SO2C 6H4-1′-), which was the most active compound in our previous studies. Density function theory calculations suggested that hypervalent bismuthanes undergo nucleophilic addition with a biomolecule at the bismuth atom to give an intermediate ate complex. For higher antifungal activity, adjusting the lipophilicity-hydrophilicity balance, modeling the three-dimensional molecular structure around the bismuth atom, and stabilizing the ate complex appear to be more important than tuning the Lewis acidity at the bismuth atom.
Homo- And heteroleptic bismuth(iii/v) thiolates from N-heterocyclic thiones: Synthesis, structure and anti-microbial activity
Luqman, Ahmad,Blair, Victoria L.,Andrews, Philip C.,Brammananth, Rajini,Crellin, Paul K.,Coppel, Ross L.
, p. 14362 - 14377 (2015/04/14)
Homo- and heteroleptic bismuth thiolato complexes have been synthesised and characterised from biolog,ically relevant tetrazole-, imidazole-, thiadiazole- and thia-zole- based heterocyclic thiones (thiols): 1-methyl-1 H-tetra-zole- 5-thiol (1-MMTZ(H)); 4-
Anti-leishmanial activity of novel homo- and heteroleptic bismuth(iii) thiocarboxylates
Andrews, Philip C.,Junk, Peter C.,Kedzierski, Lukasz,Peiris, Roshani M.
, p. 1297 - 1305 (2013/10/22)
Two new thiocarboxylic acids, p-bromothiobenzoic BTA and thionaphthoic acid TNA, and five new homo- and heteroleptic bismuth(iii) compounds derived from thiocarboxylic acids: [Bi{S(C≤O)C6H4Br}3] 1, [PhBi{S(C≤O)C6H4Br}2] 2, [Bi{S(C≤O)C10H7}3] 3, [PhBi{S(C≤O)C10H7}2] 4, and [Ph2Bi{S(C≤O)C10H7}] 5 were synthesised and fully characterised. The solid-state structure of complex [PhBi{S(C≤O)C6H4Br}2] 2 was confirmed by X-ray crystallography. In complex 2, the two thiocarboxylate ligands are coordinated to the bismuth(iii) centre in a didentate fashion, forming a distorted octahedral geometry in which the phenyl group and the lone pair are oriented axial to the plane formed by the two thiocarboxylate ligands. Long-range Bi-S interactions (3.54A) link these monomeric units to form a one-dimensional polymer. These compounds, in addition to six previously synthesised complexes: [Bi{SC(≤O)C6H5}3] 6, [PhBi{SC(≤O)C6H5}2] 7, [Ph2Bi{SC(≤O)C6H5}] 8, [Bi{SC(≤O)C6H4NO2}3] 9, [PhBi{SC(≤O)C6H4NO2}2] 10, and [PhBi{SC(≤O)C6H4SO3}] 11, and the thiocarboxylic acids themselves, were assessed for their in vitro activity against Leishmania major promastigotes, and for general toxicity against human fibroblast cells. The thiocarboxylic acids, with the exception of thiobenzoic acid and sulfothiobenzoic acid, were toxic to both L. major parasites and the mammalian cells at high concentrations of 50-100M. The bismuth(iii) thiocarboxylate derivatives proved to be more active than the corresponding acids. Among these, the heteroleptic phenyl-substituted bismuth(iii) complexes 2, 4, 5, and 7 were highly active, showing IC50 (half maximal inhibitory concentration) values ranging from 0.39 to 4.69M, and a clear ligand dependence on activity.
Study of homo- and cross-coupling competition in the reaction of triarylbismuth(V) dicarboxylates with methyl acrylate in the presence of a palladium catalyst
Moiseev, Dmitry V.,Malysheva, Yulia B.,Shavyrin, Andrey S.,Kurskii, Yury A.,Gushchin, Aleksey V.
, p. 3652 - 3663 (2007/10/03)
Triarylbismuth(V) derivatives Ar3Bi(O2CR)2 (Ar = Ph, m-Tol, p-Tol; R = H, Me, Et, n-Bu, t-Bu, n-C5H 11, CF3, CH2Cl, CCl3, Ph) were prepared in good to excellent yields by reaction of Ar3Bi with equimolar amounts of t-BuOOH in the presence of an acid. These compounds were tested in the C-arylation reaction of methyl acrylate, as a model substrate, in the presence of palladium catalyst (4 mol%). It was found that triphenylbismuth dicarboxylates are very active phenylating agents under mild conditions (20 °C). The effect of the carboxylic group, the effect of the nature of the palladium catalyst and the effect of oxygen on the reactivity of the organobismuth compounds and on the selectivity of the C-arylation reaction were studied. Methyl cinnamate, the C-phenylation product, and biphenyl, the homo-coupling by-product, were obtained in all cases. Triphenylbismuth divalerate Ph3Bi(O2CBu)2 is the most reactive compound among the triphenylbismuth dicarboxylates studied.
Acyl derivatives of main group metals: preparation of benzoyl derivatives of some group V and VI metals and metalloids
Asthana, Anju,Srivastava, Ramesh C.
, p. 281 - 286 (2007/10/02)
3,5-Dinitrobenzoyl chloride (1) adds oxidatively to triarylantimony to give the first benzoyl derivatives of antimony, ArSbCl.Triphenyl-phosphine and -arsine, and also bis(p-methoxyphenyl)tellurium(II) react with 1 in the same way.Conductivity and molecular weight data show that the benzoyl derivatives exist in solution as monomeric species.The metal-acyl bond in the compounds is stable towards MeOH, MeI, and CdX2.Reaction of 1 with triphenylbismuth leads to the cleavage of one Bi-Ph bond.Attempts to prepare the benzoyl derivative, Ph3PbCOC6H3(NO2)2, by the reaction of 1 with hexaphenyldilead were unsuccessful, but one Pb-Ph bond was cleaved of Ph4Pb in the presence of 1.
New Reagents, XXXII, Alkyldiphenylbismutanes: Synthesis, Properties, and Halogenolysis
Kauffmann, Thomas,Steinseifer, Fritz
, p. 1031 - 1038 (2007/10/02)
Alkyldiphenylbismutanes 1 have been synthesized for the first time (61-92 percent).These compounds are air sensitive, not spontaneously inflammable liquids which decompose not below ca. 170 deg C.The diphenylbismutino group is very good equivalent for Cl- or Br-substituents at aliphatic residues since halogenolysis of the Bi-Alk bond with SO2Cl2 or Br2 already occurs at -40 to 0 deg C (corresponding fissions of As-Alk and Sb-Alk bonds afford heating to ca. 130 or ca. 220 deg C).
