24756-10-3Relevant academic research and scientific papers
Arylazo-3,5-dimethylisoxazoles: Azoheteroarene Photoswitches Exhibiting High Z-Isomer Stability, Solid-State Photochromism, and Reversible Light-Induced Phase Transition
Devi, Sudha,Kumar, Pravesh,Sah, Chitranjan,Srivastava, Anjali,Venkataramani, Sugumar
supporting information, (2019/08/21)
Reversibly photoswitchable phenylazo-3,5-dimethylisoxazole and 37 aryl-substituted derivatives were synthesized. Excellent photoswitching ability of these compounds in solution and the solid state was demonstrated. Through kinetics studies by means of NMR spectroscopy, high Z-isomer stability was demonstrated. Interestingly, the majority of the derivatives showed light-induced contrasting color changes in solution and the solid state. Besides, many of the derivatives exhibit partial phase transition upon UV irradiation. The highlight of this class of photoswitches is the reversible light-induced phase transition between solid and liquid phases in the parent compound, which can be used in patterned crystallization. These results show that this new class of azoheteroarene based photoswitches has opportunities to be useful in various domains.
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.
Synthesis and structural study of 2′- and 2′,6′- positioned methyl- and nitro-substituted 3-(arylhydrazono)pentane-2,4-diones
Marten, Jan,Seichter, Wilhelm,Weber, Edwin,Boehme, Uwe
, p. 716 - 731 (2008/03/13)
A systematic series of ortho-methyl- and nitro-substituted arylhydrazones 2-6 formed by Japp-Klingemann reaction between pentane-2,4-dione and the respective aryldiazonium salts have been synthesized and studied by X-ray crystal structure analysis, with a
Arylamidrazones as novel corticotropin releasing factor receptor antagonists
Wilson, Dean M.,Termin, Andreas P.,Mao, Long,Ramirez-Weinhouse, Michele M.,Molteni, Valentina,Grootenhuis, Peter D. J.,Miller, Keith,Keim, Susan,Wise, Gwendolyn
, p. 2123 - 2126 (2007/10/03)
The arylamidrazones have been found to be potent corticotropin releasing factor (CRF) receptor antagonists structurally distinct from previously reported CRF1 antagonists. Attempts to modify the arylamidrazone core suggested an important role f
13C N.M.R. Examination of Ethyl Cyano(arylhydrazono)acetates
Prasad, Durgeshwari,Prasad, Nagendra,Prasad, Radha M.,Ferrier, Robert J.,Milgate, Stephen M.
, p. 1397 - 1399 (2007/10/02)
The products of the condensation of aryldiazonium salts with ethyl cyanoacetate are the (Z)- and (E)-isomers of the hydrazono forms.These have been examined separately by 13C n.m.r. spectroscopy which allows their specific identification.The ef
