622-73-1

Basic information

• Product Name: 1-(4-methoxybenzylidene)-2-phenylhydrazine
• CAS NO: 622-73-1
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.2738
• Mol File: 622-73-1.mol
• Article Data: 59

Chemical Properties

• Boiling Point: 364.8°C at 760 mmHg
• Flash Point: 174.5°C
• Density: 1.04g/cm³
• Vapor Pressure: 1.64E-05mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 1-(4-methoxybenzylidene)-2-phenylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxybenzylidene)-2-phenylhydrazine(622-73-1)
• EPA Substance Registry System: 1-(4-methoxybenzylidene)-2-phenylhydrazine(622-73-1)

Safety Data

• Hazardous Substances Data: 622-73-1(Hazardous Substances Data)

Usage

Description

1-(4-methoxybenzylidene)-2-phenylhydrazine is a hydrazine derivative with the chemical formula C15H15N3O, featuring a benzylidene group and a phenyl group. This chemical compound is known for its potential applications in the pharmaceutical and agrochemical industries, as well as its biological activities.

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 
• 108-88-3 toluene 
• 836-41-9 p-methoxybenzylidene-phenylamine 
• 64-17-5 ethanol 
• 22013-86-1 1-(2-bromo-2-nitrovinyl)-4-methoxybenzene 
• 16061-98-6 4-methoxybenzaldehyde oxime benzoyl ester 
• 59-88-1 phenylhydrazine hydrochloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 108-98-5 thiophenol 
• 2746-25-0 p-Methoxybenzyl bromide 
• 40277-63-2 4-methoxy-N'-phenylbenzohydrazonoyl chloride 

Downstream Products

• 62031-25-8 phenylazo-p-anisoylaldoxime 
• 69084-29-3 4-(4-methoxyphenyl)-2,7-diphenyl-6,8-dioxo-2,3,7-triazabicyclo<3.3.0>octane 
• 104707-28-0 C₂₁H₁₉N₃O₂ 
• 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 
• 100-09-4 4-methoxybenzoic acid 
• 909774-67-0 (4-methoxy-α-nitro-benzylidene)-phenyl-hydrazine 
• 1833-18-7 4-methoxy-N²-(4-methoxy-benzylidene)-N¹,N⁴-diphenyl-benzohydrazidine 

Relevant articles and documents

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.

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.

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.