21099-35-4Relevant academic research and scientific papers
The possible tautomerism of the potential rotary switch 2-(2-(2-Hydroxy-4-nitrophenyl)hydrazono)-1-phenylbutane-1,3-dione
Hristova, Silvia,Kamounah, Fadhil S.,Molla, Nevse,Hansen, Poul Erik,Nedeltcheva, Daniela,Antonov, Liudmil
, p. 249 - 261 (2017)
The title compound is potentially tautomeric and its tautomerism was studied by means of molecular spectroscopy (1H and 13C NMR and UV–Vis) in DMSO as well as by quantum chemical calculations (M06-2X/TZVP). The detailed assignment of the NMR signals supported by the theoretical calculations clearly shows that the previous interpretation, available in the literature, about the coexistence of two tautomeric forms is not correct. The compound exists as major and minor isomer of a single tautomeric form. In addition, a 2-methoxy derivative (the OH group replaced by a methoxy group) is also investigated and show similar trends.
2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma
Viswanathan, Anisha,Kute, Dinesh,Musa, Aliyu,Konda Mani, Saravanan,Sipil?, Vili,Emmert-Streib, Frank,Zubkov, Fedor I.,Gurbanov, Atash V.,Yli-Harja, Olli,Kandhavelu, Meenakshisundaram
, p. 291 - 303 (2019/02/07)
Nerve growth factor receptor (NGFR), a member of kinase protein, is emerging as an important target for Glioblastoma (GBM) treatment. Overexpression of NGFR is observed in many metastatic cancers including GBM, promoting tumor migration and invasion. Hydrazones have been reported to effectively interact with receptor tyrosine kinases (RTKs). We report herein the synthesis of 23 arylhydrazones of active methylene compounds (AHAMCs) compounds and their anti-proliferative activity against GBM cell lines, LN229 and U87. Compound R234, 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile, was identified as the most active anti-neoplastic compound, with the IC50 value ranging 87 μM - 107 μM. Molecular docking simulations of the synthesized compounds into the active site of tyrosine receptor kinase A (TrkA), demonstrated a strong binding affinity with R234 and concurs well with the obtained biological results. R234 was found to be a negative regulator of PI3K/Akt/mTOR pathway and an enhancer of p53 expression. In addition, R234 treated GBM cells exhibited the downregulation of cyclins, cyclin-dependent kinases and other key molecules involved in cell cycle such as CCNE, E2F, CCND, CDK6, indicating that R234 induces cell cycle arrest at G1/S. R234 also exerted its apoptotic effects independent of caspase3/7 activity, in both cell lines. In U87 cells, R234 induced oxidative effects whereas LN229 cells annulled oxidative stress. The study thus concludes that R234, being a negative modulator of RTKs and cell cycle inhibitor, may represent a novel class of anti-GBM drugs.
Quantum chemical simulations of solvent influence on UV-vis spectra and orbital shapes of azoderivatives of diphenylpropane-1,3-dione
Kuznik,Kityk,Kopylovich,Mahmudov,Ozga,Lakshminarayana,Pombeiro
supporting information; experimental part, p. 1287 - 1294 (2011/04/16)
The DFT modeling of novel synthesized azoderivatives of β-diketones - 2-(2-(2-hydroxyphenyl)hydrazono)-1,3-diphenylpropane-1,3-dione (1), 2-(2-(2-hydroxy-4-nitrophenyl)hydrazono)-1,3-diphenylpropane-1,3-dione (2), 3-(2-(1,3-dioxo-1,3-diphenylpropan-2-ylid
