4096-88-2Relevant articles and documents
Metallacycle-catalyzed SNAr reaction in water: Supramolecular inhibition by means of host-guest complexation
Lopez-Vidal, Eva M.,Fernandez-Mato, Antonio,Garcia, Marcos D.,Perez-Lorenzo, Moises,Peinador, Carlos,Quintela, Jose M.
, p. 1265 - 1270 (2014)
The performance of a PtII diazapyrenium-based metallacycle as a reusable substoichiometric catalyst for the SNAr reaction between halodinitrobenzenes and sodium azide at rt in aqueous media is reported. The results suggest that the c
Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model
Jia, Yan,Si, Lihui,Lin, Ruixin,Jin, Hongjuan,Jian, Wenwen,Yu, Qing,Yang, Shuli
, p. 62 - 70 (2019/04/04)
In the present study a library of thiophenol-formaldehyde-triazole (TFT) derivatives was synthesized and screened against CAOV3, CAOV4 and ES-2 ovary cancer cell lines. Initial screening revealed that five-compounds 5a, 5b, 5j, 5h and 5i inhibited the viability of tested cell lines. Analysis of apoptosis revealed that increase in compound 5a (most active) concentration from 0.25 to 2.0 μM enhanced apoptotic cell proportion. Transwell assay showed reduction in invasive potential of CAOV3 cells on treatment with compound 5a. In wound healing assay increasing the concentration of compound 5a from 0.5 to 2.0 μM caused a significant (P 0.05) decrease in the migration potential. Western blotting showed that compound 5a treatment markedly decreased the level of matrix metalloproteinase (MMP)-2 and ?9 in CAOV3 cells. Treatment of CAOV3 cells with compound 5a caused a marked decrease in Focal Adhesion Kinase (FAK) activation. Tumor growth was inhibited in the compound 5a treated mice markedly than those of untreated group. The tumor metastasis to liver, intestine, spleen and peritoneal cavity was markedly decreased in mice treated with 10 mg/kg dose of compound 5a. Examination of Von Willebrand factor (vWF) expression in liver, intestinal and pulmonary lesions showed a marked decrease in the compound 5a-treated mice. The infiltration of macrophages in the metastatic lesions showed a significant decrease in compound 5a-treated mice. In conclusion, the compound 5a inhibited ovary cancer cell viability and induced apoptosis through decrease in expression of vWF and metalloproteinase, suppression of FAK activation and decrease in infiltration of macrophages. The compound 5a therefore can be investigated further for the treatment of ovary cancer.
The α-effect in the SNAr reaction of 1-(4-nitrophenoxy)-2,4-dinitrobenzene with anionic nucleophiles: Effects of solvation and polarizability on the α-effect
Um, Ik-Hwan,Kim, Min-Young,Cho, Hyo-Jin,Dust, Julian M.,Buncel, Erwin
, p. 1109 - 1114 (2015/10/06)
A kinetic study on SNAr reactions of 1-(4-nitrophenoxy)-2,4-dinitrobenzene (1a) with various anionic nucleophiles in 80 mol% water-20 mol% DMSO at 25.0 °C is reported. The Bronsted-type plot for the reaction of 1a with a series of substituted phenoxides and HOO- results in an excellent linear correlation with βnuc = 1.17. However, OH- exhibits dramatic negative deviation from the Bronsted-type plot, while N3-, C6H5S-, and butane-2,3-dione monoximate (Ox-) deviate positively from linearity. HOO- is 680-fold more reactive than OH- but does not exhibit the α-effect. In contrast, Ox- is 166-fold more reactive than isobasic 4-Cl-C6H4O- and exhibits the α-effect. Differential solvation effects have been suggested to be responsible for the α-effect in this study, i.e., Ox- exhibits the α-effect, since it is 5.7 kcal/mol less strongly solvated than 4-Cl-C6H4O- in the reaction medium, while HOO- does not show the α-effect due to a strong requirement for partial desolvation before nucleophilic attack. The highly enhanced reactivity of polarizable N3- and C6H5S- and extremely decreased reactivity of nonpolarizable OH- are in accord with the hard-soft acid and base principle.