- Bioactive heteroleptic Bismuth(V) carboxylates: Synthetic Stratagem, characterization and binding pattern validation
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A series of heteroleptic triorganobismuth(V) carboxylates (1–8) of general formula Ar3Bi(COOR)2; where Ar = C6H5 (1–4), p-CH3C6H4 (5–8) and R = C10H7 (1, 5), 2-CH3C6H4 (2, 6), 3, 4- (OCH2CH3)C6H3 (3, 7), 2-ClC6H4 (4, 8); were synthesized by a stoichiometric reaction between the precursor, Ar3BiBr2, and the respective carboxylic acidusing triethylamine as a base in dry toluene. They were characterized by FT-IR, NMR spectroscopy and X-ray diffraction technique to get unequivocal evidence for their structural motifs. The single crystal XRD data for (2 & 5) revealed the existence of five coordinated bismuth centre having distorted trigonal bipyramidal molecular geometry, whereas (6) described weakly hexacoordinated bismuth including a unique anisobidentate interaction of one carboxyl group with the resultant distorted octahedral molecular geometry. The molecular docking studies demonstrate that compounds (1, 2 and 7) give significant GOLD fitness scores of 60.09, 62.65 and 56.30 against EGFR tyrosine kinase, human pancreatic alpha amylase and H. pylori urease respectively. The synthesized compounds were also preliminary screened for their antimicrobial, α-amylase inhibition and protein kinase inhibition activities to determine their biological efficacy. The antibacterial activity profile for (2) looks good with MIC value 6.25 μg/mL against E. coli whereas, (1, 2 and 5) show significant antifungal activity against A. flavus having MIC value of 6.25 μg/mL and the values are comparable to the reference drug(s). Compound (6) displays significant % alpha amylase inhibition of 34.80, whereas (2) exhibit 30 mm bald inhibition zone for protein kinase inhibition study, thus, proving their worth as moderate enzyme inhibitors. The molecular docking studies for (1–8) demonstrate strong interactions between the receptor and the molecule and a firm protein-ligand complex formation described their effective role in enzymes’ inhibition. The bioactivity data obtained from both in silico analysis and in vitro studies are quite promising ones and the synthesized compounds may find a leading role in future drug discovery programs.
- Abbas, Sumaira,Azam, Syed Sikander,Ihsan-ul-Haq,Imtiaz-ud-Din,Mehmood, Mehwish,Parvaiz, Nousheen,Tahir, Muhammad Nawaz,Tameez Ud Din, Asim
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- In situ quenching of monoaryl bismuth (III) dihalides with nitrogen donor ligands: Isolation of adducts and their spectral characterization
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The molecular addition of amphoteric molecules of organobismuth (III) compounds namely, o-tolylbismuth and p-tolylbismuth dihalides with nitrogen donor bidentate ligands 1, 10 phenanthroline and 2, 2′-bipyridine have been isolated and characterized by UV–
- Jadhav,Pardeshi
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p. 876 - 884
(2018/09/18)
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- Synthesis and structure of bis(2,6-dibromo-4-chlorophenoxy)triphenylbismuth and dibromotriphenylbismuth
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Bis(2,6-dibromo-4-chlorophenoxy)triphenylbismuth and dibromotriphenylbismuth were synthesized by the reaction of triphenylbismuth, 2,6-dibromo-4-chlorophenol, and hydrogen peroxide (1:2:1 molar ratio) in diethyl ether. The structure of these compounds was determined by X-ray crystallography. The coordination polyhedra of the Bi atoms are distorted trigonal bipyramids with aryloxy groups or bromine atoms in axial positions. The Bi-C, Bi-O, and Bi-Br bond lengths are 2.184(6)-2.216(4), 2.241(3), 2.245(3), and 2.7262(9) and 2.7384(9) ?, respectively. The intramolecular contacts Bi?Br(1,4) in triphenylbismuth diaryloxide are 3.850(1) and 3.965(1) ?, respectively.
- Sharutin,Egorova,Tsiplukhina,Ivanenko,Pushilin,Gerasimenko
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p. 1360 - 1365
(2008/10/09)
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- Synthesis and structure of pentavalent bismuth(V) alkoxides and ligand redistribution equilibria in solution
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The six new pentavalent Bi(V) alkoxide complexes Ph3Bi(OR)2, 1, Ph3BiBr(OR), 2, and Ph4Bi(OR), 3 (a, R = C6F5; b R = C6Cl5) have been prepared. Ph4Bi(OR) was synthesized by alcoholysis of BiPh5 with ROH. Ph3Bi(OR)2 and Ph3BiBr(OR) were products of the salt elimination reaction between Ph3BiBr2 and NaOR. These compounds were characterized spectroscopically and by single-crystal X-ray diffraction. In the solid state, they possess distorted trigonal bipyramidal coordination geometries. Although the mixed species Ph3BiBr(OR) may be isolated in pure form as crystalline solids, they do not exist as pure compounds in solution owing to the very rapid redistribution equilibrium Ph3Bi(OR)2 + Ph3BiBr2 ? 2Ph3BiBr(OR). The equilibrium constants were measured using VT NMR spec-troscopy. For comparison, the equilibrium constants for the previously unreported cross-exchange reactions between the dihalides Ph3BiX2 (X = F, Cl, Br) were also measured at 226 K. Trends observed in the values of Keq correlate with the difference in the electro-negativity of the mixed X species. The thermal stabilities of Ph3Bi(OR)2 were examined in toluene solution and in the solid state. Pyrolysis results in elimination of ROPh for both R = C6F5 and C6Cl5.
- Hoppe, Silke,Whitmire, Kenton H.
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p. 1347 - 1354
(2008/10/08)
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- Unexpected Formation of Triarylbismuth Diformates in the Oxidation of Triarylbismuthines with Ozone at Low Temperatures
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Oxidation of triphenylbismuthine 1 with ozone in toluene at -78 deg C gave, unexpectedly, a high yield of triphenylbismuth diformate 3, which was also obtainable as a minor product by a similar oxidation in ethyl acetate and acetone.An X-ray crystallographic study revealed that compound 3 has C2 symmetry, the geometry around the bismuth atom being best described as a distorted trigonal bipyramid as a result of strong intramolecular interaction between the bismuth and carbonyl oxygen atoms.Treatment of compound 3 with aqueous sodium acetate or halides readily converted it into the corresponding triphenylbismuth diacetate 5 or dihalides 7 - 9.
- Suzuki, Hitomi,Ikegami, Tohru,Matano, Yoshihiro,Azuma, Nagao
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p. 2411 - 2416
(2007/10/02)
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