622-73-1

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-methoxybenzylidene)-2-phenylhydrazine is used as an intermediate compound for the synthesis of various pharmaceuticals. Its application is due to its structural properties that can be further modified to create new drugs with potential therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(4-methoxybenzylidene)-2-phenylhydrazine is used as a building block for the development of new agrochemicals. Its use is attributed to its ability to be incorporated into molecules with pesticidal or herbicidal properties.
Used in Antitumor Applications:
1-(4-methoxybenzylidene)-2-phenylhydrazine is used as an antitumor agent due to its potential to exhibit antitumor activity. 1-(4-methoxybenzylidene)-2-phenylhydrazine is being studied for its ability to target and inhibit the growth of cancer cells.
Used in Antifungal Applications:
1-(4-methoxybenzylidene)-2-phenylhydrazine is also used as an antifungal agent, leveraging its potential to combat fungal infections by disrupting the growth and survival of fungi.
Used in Alzheimer's Disease Research:
1-(4-methoxybenzylidene)-2-phenylhydrazine is used in the research and development of treatments for Alzheimer's disease, as it has shown activity against the neurodegenerative condition.
Used in Antioxidant Therapies:
Due to its antioxidant and free radical scavenging properties, 1-(4-methoxybenzylidene)-2-phenylhydrazine is a potential candidate for use in the development of antioxidant therapies, which could help in the treatment of various diseases and conditions associated with oxidative stress.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 100-63-0 phenylhydrazine 
• 6292-71-3 4-methoxybenzaldehyde semicarbazone 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 16061-98-6 4-methoxybenzaldehyde oxime benzoyl ester 
• 59-88-1 phenylhydrazine hydrochloride 
• 40277-63-2 4-methoxy-N'-phenylbenzohydrazonoyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 108-98-5 thiophenol 
• 62-53-3 aniline 
• 3717-21-3 p-methoxyl benzaldoxime 
• 22013-86-1 1-(2-bromo-2-nitrovinyl)-4-methoxybenzene 

Downstream Products

• 62031-25-8 phenylazo-p-anisoylaldoxime 
• 104936-70-1 3-(4-Methoxy-phenyl)-5-methyl-1-phenyl-1H-[1,2,4]triazole 
• 123-11-5 4-methoxy-benzaldehyde 
• 104936-71-2 5-Ethyl-3-(4-methoxy-phenyl)-1-phenyl-1H-[1,2,4]triazole 
• 123560-34-9 4-methoxybenzaldehyde α-chloroformylphenylhydrazone 
• 128737-93-9 2,4,7-Trinitro-fluoren-9-one; compound with N-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-N'-phenyl-hydrazine 
• 129159-29-1 2-{4-[2-4-methoxybenzylidenehydrazino]phenyl}ethylene-1,1,2-tricarbonitrile 
• 128738-02-3 2-(2,4,7-Trinitro-fluoren-9-ylidene)-malononitrile; compound with N-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-N'-phenyl-hydrazine 
• 134122-61-5 3-(p-methoxyphenyl)-5-(1,2,3,4,5-penta-O-acetyl-D-galacto-pentitol-1-yl)-1-phenylpyrazole 
• 56156-39-9 1,5-diphenyl-3-(p-methoxyphenyl)formazane 
• 112718-20-4 2-[3-(4-methoxy-phenyl)-N'''-phenyl-formazano]-benzoic acid 
• 92-52-4 biphenyl 
• 7684-30-2 N,N-dimethyl-N'-phenylcarbamimidic chloride 
• 874-90-8 4-methoxybenzonitrile 

Relevant academic research and scientific papers

Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol

This research work involved preparation of heterogeneous pent lateral cyclic compounds (thiazolidine -4- one, benzothiazole, triazole, 4-oxothiazolidin) using thiophenol as raw materials: Thiophenol was reacted with mono chloroacetic acid in the presence of potassium hydroxide to prepare (sh1) followed by ortho amino aniline results the (sh2). The reaction of thiophenol with ethylchloroacetate afforded (sh3) and the reaction of (sh3) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4- triazole (sh5). A treatment of thiophenol with hydrazine hydrate to obtain the intermediate (sh6) with aromatic aldehyde synthesized azomethines (sh7- sh9) then treated with mercaptoacetic acid to obtained (sh10-sh12). A treatment of thiophenol with chloroacetyl chloride produced (sh13) compound then treated with hydrazine hydrate to obtain (sh14) compound followed by bromobenzaldehyde synthesized azomethine (sh15) compound then treated with mercaptoacetic acid to obtained (sh16) compound. Characterization results for the prepared compounds using IR spectroscopy, NMR and melting points confirmed their chemical structures.

Synthesis of 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) and 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) Perchlorates

Abstract: New bis-formazans and bis(5,6-dihydro-1,2,4,5-tetrazin-1-ium) perchlorates were synthesized with high yields under mild conditions. 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) were obtained by diazo coupling of para-substituted benzaldehyde phenylhydrazones with [1,1′-biphenyl]-4,4′-bis(diazonium chloride). Treatment of the obtained bis-formazans with formaldehyde in the presence of perchloric acid in dioxane afforded 1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) diper-chlorates. The structure of the synthesized compounds was confirmed by elemental analyses and UV, IR, and 1H and 13C NMR spectra.

Broad-Spectrum Antifungal Agents: Fluorinated Aryl- and Heteroaryl-Substituted Hydrazones

Fluorinated aryl- and heteroaryl-substituted monohydrazones displayed excellent broad-spectrum activity against various fungal strains, including a panel of clinically relevant Candida auris strains relative to a control antifungal agent, voriconazole (VRC). These monohydrazones displayed less hemolysis of murine red blood cells than that of VRC at the same concentrations, possessed fungicidal activity in a time-kill study, and exhibited no mammalian cell cytotoxicity. In addition, these monohydrazones prevented the formation of biofilms that otherwise block antibiotic effectiveness and did not trigger the development of resistance when exposed to C. auris AR Bank # 0390 over 15 passages.

Colorimetric quantification of α-tocopherol (vitamin E) in pure form and different comestible samples by using newly synthesized tetrazolium salts

A quick, susceptible, and viable spectrophotometric procedure for the assay of α-tocopherol by newly synthesized tetrazolium reagents 2-phenyl-3-(2-thiazolyl)-5-(4-methoxyphenyl)tetrazolium bromide (PTMPT) and 2-phenyl-3-(2-thiazolyl)-5-(4-nitrophenyl)tet

Identification of novel 1,3-diaryl-1,2,4-triazole-capped histone deacetylase 6 inhibitors with potential anti-gastric cancer activity

Histone deacetylase 6 (HDAC6) has emerged as a critical regulator of many cellular pathways in tumors due to its unique structure basis and abundant substrate types. Over the past few decades, the role played by HDAC6 inhibitors as anticancer agents has sparked great interest of biochemists worldwide. However, they were less reported for gastric cancer therapy. In this paper, with the help of bioisosteric replacement, in-house library screening, and lead optimization strategies, we designed, synthesized and verified a series of 1,3-diaryl-1,2,4-triazole-capped HDAC6 inhibitors with promising anti-gastric cancer activities. Amongst, compound 9r displayed the best inhibitory activity towards HDAC6 (IC50 = 30.6 nM), with 128-fold selectivity over HDAC1. Further BLI and CETSA assay proved the high affinity of 9r to HDAC6. In addition, 9r could dose-dependently upregulate the levels of acetylated α-tubulin, without significant effect on acetylated histone H3 in MGC803 cells. Besides, 9r exhibited potent antiproliferative effect on MGC803 cells, and promoted apoptosis and suppressed the metastasis without obvious toxicity, suggesting 9r would serve as a potential lead compound for the development of novel therapeutic agents of gastric cancer.

Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs

A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is

1,3-dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene-PTAD and biological activities of adducts formed selectively

After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4-phenyl-1,2,4-triazoline-3,5-dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3-dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (α-Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.

Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation

The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.

Synthesis and Electrochemical Properties of 2-(4-R1-Phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro1,2,4,5-tetrazin-1(2H)-yls

Abstract: A new methodology for creating electroactive components for organic batteries,based on the construction of a molecular platform including stable3,4-dihydro-1,2,4,5-tetrazin-1(2H)-ylradicals was described. A series of2-(4-R1-phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yls with substituents of various nature wasobtained. It was shown that the substituents R1 inthe aromatic ring at position 2 of the tetrazinyl fragment influence the valueof the oxidation potential in the radical, but do not influence the value of thereduction potentials, while the substituent R2 of thearomatic ring at position 6 influence the values of the reduction potentials andpractically do not influence oxidation potential values. Based on the obtainedelectrochemical data, a correlation structure–potential value was revealed forthe cathodic and anodic process, with the help of which triarylsubstituted3,4-dihydro-1,2,4,5-tetrazin-1(2H)-ylradicals with high values of the electrochemical gap were obtained.

Triarylverdazyl radicals as promising redox-active components of rechargeable organic batteries

A novel design of electroactive components of rechargeable organic batteries based on stable verdazyl radicals bearing various substituents is proposed. 3-Positioned aromatic substituents at the verdazyl moiety affect the reduction potentials and almost do not affect the oxidation potential, while 1-positioned aromatic substituents affect contrariwise the oxidation potential of this radical without any influence on the reduction potential. The acquired electrochemical data allowed us to reveal the structure—potential relationship for the cathodic and anodic processes, which provided the design of triarylverdazyl radicals possessing record-breaking parameters of the “electrochemical gap”.