59394-91-1

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 141736-86-9 Benzoic acid N-benzoyl-N'-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 1124127-48-5 dimethyl 2-[N-benzoyl-N'-(4-nitro-benzylidene)-hydrazino]-3-(cyclohexyliminomethylene)succinate 
• 1242159-25-6 (S)-N'-[1-(4-nitrophenyl)but-3-enyl]benzohydrazide 
• 1192113-36-2 (R)-N'-[1-(4-nitrophenyl)but-3-enyl]benzohydrazide 
• 134022-08-5 2-(4-nitrophenyl)-3-acetyl-5-phenyl-2,3-dihydro-1,3,4-oxadiazole 
• 32252-83-8 1-chloro-4-(4-nitrophenyl)-1-phenyl-2,3-diazabutadiene 
• 1090-82-0 2-(4-nitrophenyl)-5-phenyl-1,3,4-oxadiazole 
• 1392047-97-0 (S)-5,6-dihydro-6-(4-nitrophenyl)pyridin-2(1H)-one 
• 1392047-89-0 C₁₃H₁₄N₂O₃ 
• 1392047-82-3 (2S)-2-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine 
• 1392047-75-4 C₁₃H₁₆N₂O₂ 
• 1366284-27-6 N-(2,2-difluoro-1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)benzohydrazide 
• 1111149-05-3 dimethyl 3-(triphenyl-λ(5)-phosphanylidene)-2-(N-benzoyl-N'-(4-nitrobenzylidene)hydrazino)succinate 
• 30082-73-6 (N-(4-nitrobenzylidene)-4H-3,5-diphenyl-1,2,4-triazole-4-amine) 

Relevant academic research and scientific papers

Crystal structure of benzoic acid 4-nitrobenzylidenhydrazide

The crystal structure of benzoic acid 4-nitrobenzylidenhydrazide has been determined. Crystal data: crystal system - monoclinic, a = 7.101(9) A, b = 25.48(3) A, c = 7.730(11) A; β = 112.43(9)°, space group P21/n, Z = 4, R = 0.038. The compound under investigation has a non-planar structure in general, and the substituents at azomethine N-C bond are in E-position. Root-mean-square planes of the six-memebered heterocycles make angles of 29.9° and 37.7° to fairly planar hydrazine fragment. In crystalline state the compound forms layers, the molecules within the layers being linked by C-H...O bonds. Neighboring layers are connected by hydrogen bonds between carbonyl oxygen atoms and amide hydrogens.

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

Synthesis and biological evaluation in vitro and in silico of N-propionyl-N′-benzeneacylhydrazone derivatives as cruzain inhibitors of Trypanosoma cruzi

Abstract: An N-acylhydrazone scaffold has been used to develop new drugs with diverse biological activities, including trypanocidal activity against different strains of Trypanosoma cruzi. However, their mechanism of action is not clear, although in T. cr

Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones

The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.

Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions

Acylhydrazones formation has been widely applied in materials science and biolabeling. However, their sluggish condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional anilinecatalyzed reaction at neutral conditions. The identified indoline catalyst was successfully applied in hydrogel formation.

Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists

Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERRα emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERRβ/γ selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERRα agonism. We successfully engineered high affinity ERRα agonism into a chemical scaffold that displays selective ERRβ/γ agonist activity (GSK4716), providing novel ERRα/β/γ pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERRα. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERRα and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1α and PGC-1β, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.

Lanthanide-EDTA complexes covalently bonded on Fe3O4@SiO2 magnetic nanoparticles promote the green, stereoselective synthesis of: N-Acylhydrazones

In the last few years, many synthetic methods have been developed using magnetic nanomaterial-based catalysts with considerable advantages for the efficiency, selectivity and applicability of green procedures. In this work, lanthanide-EDTA complexes coval

Aniline Catalysed Hydrazone Formation Reactions Show a Large Variation in Reaction Rates and Catalytic Effects

Hydrazone formation reactions from aldehydes and hydrazides have the remarkable qualities that they proceed in water and the kinetics can be controlled by organocatalysis. For these reasons, this class of reactions finds widespread use in biological as well as material settings. We recently reported a protected aniline catalyst for hydrazone formation that can be activated using a chemical signal. In our search to find a suitable hydrazone formation reaction to investigate the activation of this pro-catalyst, we found a wide variety in reaction rates and response to catalysis. Here we report an overview of hydrazone formation reactions, their reaction rates and response to aniline catalysis, their compatibility for kinetic analysis by UV/Vis spectroscopy, and their compatibility with the reaction environment and with the pro-catalyst pro-aniline. (Figure presented.).

2,5-Diaryloxadiazoles and their precursors as novel inhibitors of cathepsins B, H and L

High levels of cathepsins indicated in various pathological conditions like arthritis, cancer progressions, and atherosclerosis explains the need to explore potential inhibitors of these proteases which can be of great therapeutic significance. We, in the present work, report the synthesis of some 2,5-diaryloxadiazoles from N-subsitutedbenzylidenebenzohydrazides. The synthesized compounds were screened for their inhibitory potential on cathepsins B, H and L. Structure Activity Relationship studies show that 2,5-diaryloxadiazoles were less inhibitory than their precursors. 1i and 2k have been found to be most inhibitory to cathepsins B and L. Their Ki values have been calculated as 11.38 × 10-8 M and 66.4 × 10-8 M for cathepsin B and 4.2 × 10-9 M and 47.31 × 10-9 M for cathepsin L, respectively. However, cathepsin H activity was maximally inhibited by compounds, 1e and 2c with Ki values of 4.4 × 10-7 M and 5.6 × 10-7 M, respectively. Enzyme kinetic studies suggest that these compounds are competitive inhibitors to the enzymes. The results have been compared with docking results obtained using iGemDock.

Study on DDQ-promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles from acid hydrazides and aldehydes

A facile stepwise synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles proceeding via oxidative cyclization of N-acylhydrazones is reported. The reaction is efficiently promoted by 2, 3-dichloro-5, 6-dicyano-1, 4- benzoquinone (DDQ) to afford the desired products mostly in high yields and in relatively short times. The final 1, 3, 4-oxadiazole derivatives are also synthesized directly from acid hydrazides and aldehydes in a one-pot procedure. The substrate scope and limitations of the reported transformation are discussed in detail.