2216-75-3

Basic information

• Product Name: Furaldehyde phenylhydrazone
• Synonyms: Furaldehyde phenylhydrazone
• CAS NO: 2216-75-3
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.21
• Mol File: 2216-75-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 320.7°C (rough estimate)
• Flash Point: 137.8°C
• Appearance: /
• Density: 1.1458 (rough estimate)
• Vapor Pressure: 0.000884mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• PKA: 14.44±0.10(Predicted)
• CAS DataBase Reference: Furaldehyde phenylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Furaldehyde phenylhydrazone(2216-75-3)
• EPA Substance Registry System: Furaldehyde phenylhydrazone(2216-75-3)

Safety Data

• Hazardous Substances Data: 2216-75-3(Hazardous Substances Data)

Usage

General Description

Furaldehyde phenylhydrazone is a chemical compound that is derived from furaldehyde and phenylhydrazine. It is commonly used in organic synthesis as a reagent for the detection and determination of carbonyl compounds. It forms bright yellow crystals and has a strong odor. Furaldehyde phenylhydrazone is also used as a selective reagent for the determination of aldehydes and ketones in various samples. It has been found to have potential applications in the pharmaceutical and agrochemical industries as well. Additionally, it has been studied for its potential antioxidant and antimicrobial properties, making it a versatile and valuable chemical compound.

InChI:InChI=1/C11H10N2O/c1-2-5-10(6-3-1)13-12-9-11-7-4-8-14-11/h1-9,13H/b12-9-

Upstream product

• 62-53-3 aniline 
• 98-01-1 furfural 
• 59-88-1 phenylhydrazine hydrochloride 
• 64-17-5 ethanol 
• 100873-48-1 4-furfurylidene-3-phenyl-4H-isoxazol-5-one 
• 100-63-0 phenylhydrazine 

Downstream Products

• 3688-57-1 N-phenylfuran-2-carboximidamide 
• 53616-21-0 3-[2]Furyl-1,5-diphenyl-formazan 
• 88-14-2 2-furanoic acid 
• 62-53-3 aniline 
• 617-89-0 furan-2-ylmethanamine 
• 1416008-60-0 tert-butyl 4'-tert-butyl-5'-(furan-2-yl)-2-oxo-2'-phenyl-2',4'-dihydrospiro[indoline-3,3'-pyrazole]-1-carboxylate 
• 36668-19-6 N'-phenylfuran-2-carbohydrazonoyl chloride 

Relevant articles and documents

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.

Nitrofuran drugs beyond redox cycling: Evidence of Nitroreduction-independent cytotoxicity mechanism

Nitrofurans (5-nitro-2-hydrazonylfuran as pharmacophore) are a group of widely used antimicrobial drugs but also associated to a variety of side effects. The molecular mechanisms that underlie the cytotoxic effects of nitrofuran drugs are not yet clearly understood. One-electron reduction of 5-nitro group by host enzymes and ROS production via redox cycling have been attributed as mechanisms of cell toxicity. However, the current evidence suggests that nitrofuran ROS generation by itself is uncapable to explain the whole toxic effects associated to nitrofuran consumption, proposing a nitro-reduction independent mechanism of toxicity. In the present work, a series of nitrated and non-nitrated derivatives of nitrofuran drugs were synthesized and evaluated in vitro for their cytotoxicity, ROS-producing capacity, effect on GSH-S-transferase and antibacterial activity. Our studies showed that in human cells non-nitrated derivatives were less toxic than parental drugs but, unexpectedly preserved the ability to generate intracellular ROS in similar amounts to nitrofurans despite not entering into a redox cycle mechanism. In addition, some non-nitrated derivatives although being uncapable to generate ROS exhibited the highest cell toxicity among all derivatives. Inhibition of cytosolic glutathione-S-transferase activity by some derivatives was also observed. Finally, only nitrofuran derivatives displayed antibacterial effect. Results suggest that the combined 2-hydrazonylfuran moiety, redox cycling of 5-nitrofuran, and inhibitory effects on antioxidant enzymes, would be finally responsible for the toxic effects of the studied nitrofurans on mammalian cells.

Nano BF3·SiO2: A green heterogeneous solid acid for synthesis of formazan dyes under solvent-free condition

A solvent-free, efficient and rapid approach for synthesis of formazan dyes was developed by diazotization of aromatic amines with NaNO2, nano silica-supported boron trifluoride (nano BF3·SiO2), then diazo coupling with aldehyde phenylhydrazones by grinding method at room temperature. This study aimed to overcome the limitations and drawbacks of the previous reported methods such as: low temperature, using corrosive and toxic acids and solvents, using buffer solutions, instability of aryl diazonium salts, modest yields, and long reaction times.