24756-07-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4-PENTANETRIONE 3-[N-(4-CHLOROPHENYL)HYDRAZONE] is used as a chemical intermediate for the synthesis of various pharmaceuticals and organic compounds, leveraging its unique chemical structure to facilitate the creation of new medicinal agents.
Used in Chemical Research:
In the field of chemical research, 2,3,4-PENTANETRIONE 3-[N-(4-CHLOROPHENYL)HYDRAZONE] is utilized as a ligand in coordination chemistry, contributing to the study of metal complexation and the development of novel metal-organic frameworks.
Used in Industrial Applications:
2,3,4-PENTANETRIONE 3-[N-(4-CHLOROPHENYL)HYDRAZONE] is employed in various industrial applications, capitalizing on its specific chemical properties to enhance the performance of different products and processes.

Upstream product

• 20265-96-7 p-chloroaniline hydrochloride 
• 123-54-6 acetylacetone 
• 106-47-8 4-chloro-aniline 
• 56075-36-6 1-(4-chlorophenyl)-2-(methylsulfonyl)diazene 
• 25145-04-4 (Z)-4-trimethylsiloxypent-3-en-2-one 
• 2028-74-2 p-chlorobenzenediazonium chloride 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 139038-68-9 N-(4-Chloro-phenyl)-N'-(5,7-dimethyl-2,3-dihydro-[1,4]diazepin-6-ylidene)-hydrazine 
• 139038-78-1 (Z)-3-(4-Chloro-phenylazo)-4-{2-[(Z)-2-(4-chloro-phenylazo)-1-methyl-3-oxo-but-1-enylamino]-ethylamino}-pent-3-en-2-one 
• 183273-24-7 1-(4-chlorophenyl)-3-[3-(dimethylamino)prop-2-enoyl]pyridazin-4(1H)-one 

Relevant academic research and scientific papers

Trends in properties of para-substituted 3-(phenylhydrazo)pentane-2,4- diones

Trends between the Hammett's σp and related normal, inductive σI, resonance σR, negative and positive polar conjugation and Taft's σp° substituent constants and the distance, δN-H NMR chemical shift,

Synthesis, characterization and cytotoxicity of mixed ligand Mn(II), Co(II) and Ni(II) complexes

Complexes of the type [ML'L(OH)(H2O)], where M = Ni(II), Co(II) or Mn(II), L' = isatin and HL = 3-(2-phenylhydrazono)acetylacetone, 3-(2-(4- -chlorophenyl)hydrazono)acetylacetone or 3-(2-(4-bromophenyl)hydrazono)- acetylacetone, were synthesize

Mixed isatin with 3-(2-(aryl)hydrazono)acetylacetone mn(ii), co(ii) and ni(ii) complexes: Antibacterial evaluation and molecular properties prediction

The metal complexes {Ni (II), Co (II) and Mn (II)} of 3-(2-(aryl)hydrazono)acetylacetone with isatin were synthesized and screened for their in vitro antibacterial activity against four pathogenic microorganisms {two Gram-positive and two Gram negative}.

Aryldiazenyl Radicals from Arylazo Sulfones: Visible Light-Driven Diazenylation of Enol Silyl Ethers

A versatile protocol for the diazenylation of enol silyl ethers under visible light irradiation is presented herein. The reaction is based on the underused reaction of a nitrogen-based radical (the diazenyl radical) with an enol silyl ether. Arylazo sulfones were used as photoactivatable precursors of these diazenyl radicals. The resulting azaderivatives are potentially bioactive compounds as well as starting materials for the synthesis of N-containing heterocycles. (Figure presented.).

Arylazo-3,5-dimethylisoxazoles: Azoheteroarene Photoswitches Exhibiting High Z-Isomer Stability, Solid-State Photochromism, and Reversible Light-Induced Phase Transition

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

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.

Structure-Based Rational Design of Novel Inhibitors Against Fructose-1,6-Bisphosphate Aldolase from Candida albicans

Class II fructose-1,6-bisphosphate aldolases (FBA-II) are attractive new targets for the discovery of drugs to combat invasive fungal infection, because they are absent in animals and higher plants. Although several FBA-II inhibitors have been reported, none of these inhibitors exhibit antifungal effect so far. In this study, several novel inhibitors of FBA-II from C. albicans (Ca-FBA-II) with potent antifungal effects were rationally designed by jointly using a specific protocols of molecular docking-based virtual screening, accurate binding-conformation evaluation strategy, synthesis and enzymatic assays. The enzymatic assays reveal that the compounds 3c, 3e-g, 3j and 3k exhibit high inhibitory activity against Ca-FBA-II (IC50 50 value of 2.7 μM. Importantly, the compounds 3f, 3g, and 3l possess not only high inhibitions against Ca-FBA-II, but also moderate antifungal activities against C. glabrata (MIC80 = 4-64 μg/mL). The compounds 3g, 3l, and 3k in combination with fluconazole (8 μg/mL) displayed significantly synergistic antifungal activities (MIC80 0.0625 μg/mL) against resistant Candida strains, which are resistant to azoles drugs. The probable binding modes between 3g and the active site of Ca-FBA-II have been proposed by using the DOX (docking, ONIOM, and XO) strategy. To our knowledge, no FBA-II inhibitors with antifungal activities against wild type and resistant strains from Candida were reported previously. The positive results suggest that the strategy adopted in this study are a promising method for the discovery of novel drugs against azole-resistant fungal pathogens in the future.

Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: Design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties

A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

Synthesis, characterization and antibacterial screening of new pyrazole and pyrazoline-5-one derivatives

A series of N′-(p-toluene sulphonyl)-3-methyl-4-(substituted arylhydrazono)-2-pyrazoline-5-ones and N′-(2-hydroxybenzoyl)-3,5-dimethyl- 4-(substituted arylazo)pyrazoles have been synthesized and characterized by chemical analysis, IR and 1H NMR spectral data. The compounds have been screened for antibacterial activity against Staphylococcus aureus and Escherichia coli.

Pyridazinone compounds

The present invention provides a compound which has the effect of PDE inhibition, and which is useful as a medicament for preventing or treating schizophrenia or so on. A compound of formula (I0): wherein R1 represents a substituent, R2 represents a hydrogen atom, or a substituent, R3 represents a hydrogen atom, or a substituent, Ring A represents an aromatic ring which can be substituted, and Ring B represents a 5-membered heteroaromatic ring which can be substituted, or a salt thereof.