857404-98-9Relevant academic research and scientific papers
In vitro anti-glioblastoma activity of L-valine derived boroxazolidones
Viswanathan, Anisha,Sebastianelli, Giulia,Brown, Kenna,Raunio, Janne,Sipil?, Vili,Yli-Harja, Olli,Candeias, Nuno R.,Kandhavelu, Meenakshisundaram
, p. 194 - 200 (2019)
In the present study, a series of L-valine derived boroxazolidones, previously synthesized and reported to have residual activity in a human epithelial cell line, have been evaluated in vitro for their anti-glioblastoma activity. A boroxazolidone derivative containing 2,4-difluorophenyl moieties (6) was found to have higher cytotoxicity than the standard drug, Temozolomide (TMZ). Compound 6 was found to exhibit dose-dependent growth inhibitory effects with an IC50 of 49 μM and 53 μM for LN229 and SNB19 cells, respectively. Additionally, 6 was assessed for its role in apoptosis, caspase 3/7 activation and oxidative stress in SNB19 and LN229 cells. SNB19 cells treated with 6 showed 45.3% apoptosis in the population, while TMZ had 24.7%. In LN229 cells, the percentage of apoptotic cells treated with compound 6 and TMZ were the same. Both 6 and TMZ induced apoptosis through the activation of caspase 3/7 in SNB19 and LN229 cells. Interestingly, 6 exhibited a higher effectivity in promoting reactive oxygen species production in LN229, while it was 6-fold less in SNB19. Boroxazolidone-treated GBM cell lines increased reactive oxygen species production, suggesting that such species may be interlinked with the observed programmed cell death. Additionally, the treatment of both GBM cell lines with 6 led to G2/M phase arrest. The magnitude of anti-GBM effect of 6 is significantly higher than the known chemotherapeutic agent TMZ. This work further demonstrates the anticancer properties of L-valine derived boroxazolidones, adding another potential derivative to the collection of promising chemotherapeutic agents for GBM treatment.
Syntheses, structures, and properties of phenyltrihydroborate complexes of zirconocene and titanocene
Liu, Fu-Chen,Chen, Jung-Hua,Chen, Shou-Chon,Chen, Ko-Yu,Lee, Gene-Hsian,Peng, Shie-Ming
, p. 291 - 300 (2007/10/03)
The phenyltrihydroborate complexes, Cp2ZrCl{(μ-H) 2BHPh}, 1, and Cp2Zr{(μ-H)2BHPh}2 ? (1/2 toluene), 2, were prepared from the reactions of Cp 2ZrCl2 with one and two moles of LiBH3Ph. The Zr-H-B bonds in 2 are stable under vacuum at 100°C for hours without significant decomposition. An inductive effect has been proposed for this strong interaction. This hydrogen bridge bond can be broken upon reacting with the Lewis base N(C2H5)3 to produce (C 2H5)3N ? BH2Ph and the zirconium hydride compound Cp2ZrH{(μ-H)2BHPh}, 3. Compound 3 also can be prepared from the reaction of Cp2ZrHCl with LiBH3Ph. The reaction of 1 with the Lewis acid B(C6F 5)3 is solvent dependent, the metathesis product Cp 2ZrCl{(μ-H)2B(C6F5)2}, 4, was formed in the toluene solution, whereas the ionic complex [Cp 2ZrCl(OEt2)][HB(C6F5)3], 5, was isolated from the ether solution. The reaction of titanocene dichloride, Cp2TiCl2, with LiBH3Ph produced a 17-electron, paramagnetic complex, Cp2Ti{(μ-H)2BHPh}, 6. Single crystal X-ray structures of 1, 2, 3, 4, 5, and 6 were also determined. A coplanar structure of the four bridge hydrogens in 2 was observed.
Synthesis and reactivity of the metal-substituted borane (CO)4CoBH2·THF. Preparation of the ambiphilic clusters (CO)9Co3C(CH2)nOH (n = 4, 5)
Basil, John D.,Aradi, Allen A.,Bhattacharyya, Nripendra K.,Rath, Nigam P.,Eigenbrot, Charles,Fehlner, Thomas P.
, p. 1260 - 1270 (2008/10/08)
The reaction Co2(CO)8 + 2BH3·THF → 2(CO)4CoBH2·THF (I) + H2 has been demonstrated to occur cleanly at -15°C in THF. I has been characterized by low-temperature 11B NMR and infrared spectroscopies as well as classical chemical analysis. The formation of I bears a remarkable similarity to that of (CO)4CoSiR3. Displacement of the bound THF of I occurs with Lewis bases, and the Lewis acidity of I relative to that of BH3·THF for SMe2 has been estimated. Displacement of [Co(CO)4]- from I occurs easily; e.g., reaction with PhMgBr yields PhBH2. I readily accepts hydride from [HFe2(CO)8]-, losing [Co(CO)4]- but reduces the CO ligands of hydride-free metal carbonylate anions. I is a very active reducing agent and above 10°C cleaves THF and condenses with hydrocarbyl and metal fragments to yield a mixture of clusters including an unusual tailed cluster (CO)9Co3C(CH2)nOH (n = 4,5) (II). A deuterium labeling experiment showed that four of the n carbons in the hydrocarbyl chain of II arise from THF. The results of an X-ray diffraction study suggest association of II in the solid state. [Crystals of II (the ratio of II with n = 5/n = 4 is 4) form in the space group R3 with unit cell parameters a = 34.409 (15) A?, b = 34.398 (21) A?, c = 8.575 (5) A?; β = γ = 90°, γ = 120°, V = 8789.8 A?3, and Z = 18. Solution was by direct methods, and all atoms were refined to R1 = 0.077 and R2 = 0.096 for 1443 independent reflections (Fo > 3σ(Fo)). Because of the disorder caused by the cocrystallization of species with different chain lengths, the last two atoms at the OH end of the chain could not be fully defined.] Association of II in solution is shown by a 1H NMR study, thereby demonstrating that II behaves as an ambiphilic cluster.
