74568-19-7

Upstream product

• 118-92-3 anthranilic acid 
• 123-54-6 acetylacetone 
• 1608-42-0 benzenedizolium-2-carboxylate 
• 4661-46-5 2-carboxybenzene diazonium chloride 

Downstream Products

• 129302-61-0 3-(N-Nitro-N-2-carboxyphenylhydrazono)pentane-2,4-dione 
• 1422054-51-0 C₂₇H₃₄CdN₄O₁₁ 
• 1422054-48-5 C₂₈H₃₈MnN₄O₁₂ 
• 1421765-20-9 [Zn(2-[N'-(1-acetyl-2-oxopropylidene)hydrazino]benzoic acid(-1H))2(2,2'-bipyridine)] 

Relevant academic research and scientific papers

Ultra-Low Molecular Weight Photoswitchable Hydrogelators

Two photoswitchable arylazopyrozoles form hydrogels at a concentration of 1.2 % (w/v). With a molecular weight of 258.28 g mol?1, these are the lowest known molecular weight hydrogelators that respond reversibly to light. Photoswitching of the E- to the Z-form by exposure to 365 nm light results in a macroscopic gel→sol transition; nearly an order of magnitude reduction in the measured elastic and loss moduli. In the case of the meta-arylazopyrozole, cryogenic transmission electron microscopy suggests that the 29±7 nm wide sheets in the E-gel state narrow to 13±2 nm upon photoswitching to the predominantly Z-solution state. Photoswitching for meta-arylazopyrozole is reversible through cycles of 365 nm and 520 nm excitation with little fatigue. The release of a rhodamine B dye encapsulated in gels formed by the arylazopyrozoles is accelerated more than 20-fold upon photoswitching with 365 nm light, demonstrating these materials are suitable for light-controlled cargo release.

2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma

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.

Complexes of Zn(II) containing (o-)/(p-) carboxylato phenyl azo pentane 2,4-dione and 2,2′ bipyridine as ligands: Synthesis, characterization, colorimetric and fluorometric modulation in the presence of Ag+ ions

Azo-enol based ligands 2-[N′-(1-acetyl-2-oxo-propylidene) hydrazino]-benzoic acid (L1H2) and 4-[N′-(1 acetyl-2 oxo-propylidene)-hydrazino]-benzoic acid (L2H2) and their complexes [Zn(L1H)2(

New arylhydrazones of β-diketones and their optical and thermal properties

New arylhydrazones of β-diketones, 2-(2-(4,4-dimethyl-2,6- dioxocyclohexylidene)hydrazinyl) benzoic acid (1) and (Z)-ethyl-2-(2-(2- nitrophenyl)hydrazono)-3-oxobutanoate (2), have been synthesized by reaction of activated β-diketones with the corresponding aryldiazonium salts, and characterized by IR, 1H and 13C NMR spectroscopies and elemental analysis. In DMSO solution, 1 is stable exclusively in the hydrazone form, while 2 exists in DMSO and H2O solutions as a mixture of enol-azo and hydrazone tautomeric forms. In the latter case, an increase in the solvent polarity shifts the tautomeric balance to the enol-azo form. Solvatochromic, thermal and photoluminescent properties of 1, 2 and the known related 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzoic acid (3), (2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)phenyl)arsonic acid (4), (Z)-2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid (5) and 5-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2,3-dihydrophthalazine-1,4-dione (6) were studied. The obtained UV-vis absorption spectra confirm that m depends on the solvent and on the nature of AHBD, but no clear correlation was found. Upon heating, 1-3, 5 and 6 are stable up to 474 K and decompose in two steps whereas 4 decomposes in three steps starting from 343 K. The kinetic parameters of the thermal decomposition were estimated suggesting a low rate of the thermal decomposition. Compounds 2 and 3 exhibit luminescence with intense emission bands with maxima at λem of 466.0 (λex = 318 nm) and 532.5 nm (λex = 315 nm), respectively, while compounds 4 and 6 show low-intensity bands at λem of 501 (λex = 396 nm) and 503 nm (λex = 389 nm). Compounds 1 and 5 display no photoluminescence.

High-Resolution 1H and 13C NMR Spectroscopy of Some Hydrazo Compounds

o-Benzenediazonium carboxylates couple with methylene-active compounds to yield hydrazo derivatives with high purity.The 1H and 13C NMR data of eleven such products are presented and analysed.The predominance of the hydrazo over the azo form is consistent with accepted criteria.Furthermore, evidence for the preference of the carbethoxy group over the acetyl group for intramolecular hydrogen bonding is suggested.KEY WORDS 1H NMR 13C NMR o-Benzenediazonium carboxylates Hydrazo compounds