726-50-1

Basic information

• Product Name: 1-[(5-nitrofuran-2-yl)methylidene]-2-phenylhydrazine
• CAS NO: 726-50-1
• Molecular Formula: C₁₁H₉N₃O₃
• Molecular Weight: 231.2075
• Mol File: 726-50-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 382.1°C at 760 mmHg
• Flash Point: 184.9°C
• Density: 1.32g/cm³
• Vapor Pressure: 4.84E-06mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 1-[(5-nitrofuran-2-yl)methylidene]-2-phenylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(5-nitrofuran-2-yl)methylidene]-2-phenylhydrazine(726-50-1)
• EPA Substance Registry System: 1-[(5-nitrofuran-2-yl)methylidene]-2-phenylhydrazine(726-50-1)

Safety Data

• Hazardous Substances Data: 726-50-1(Hazardous Substances Data)

Usage

Chemical structure

A hydrazine derivative with a furan ring and a nitro group

Usage

Often used as a precursor in the synthesis of various pharmaceuticals and organic compounds

Biological activities

Studied for its potential antimicrobial and anticancer properties

Field of interest

Medicinal chemistry and drug discovery due to its structural features

Safety concerns

Potential hazards to human health and the environment; should be handled with care

Upstream product

• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 100-63-0 phenylhydrazine 

Downstream Products

• 27301-59-3 3-(5-nitro-furan-2-yl)-1-phenyl-1H-pyrazole 
• 27301-64-0 3-(5-nitro-furan-2-yl)-1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole 
• 20066-89-1 4-benzyl-6-(5-nitro-furan-2-yl)-2-phenyl-2,3,4,5-tetrahydro-[1,2,4]triazine 
• 104707-71-3 5-(5-Nitro-furan-2-yl)-4-(4-nitro-phenyl)-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 104707-38-2 C₁₈H₁₃N₅O₆ 
• 104707-68-8 4-(3-Methoxy-phenyl)-5-(5-nitro-furan-2-yl)-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 104707-69-9 4-(4-Bromo-phenyl)-5-(5-nitro-furan-2-yl)-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 104707-70-2 4-(4-Chloro-phenyl)-5-(5-nitro-furan-2-yl)-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 104707-35-9 C₁₉H₁₆N₄O₅ 
• 104707-36-0 C₁₈H₁₃BrN₄O₄ 
• 104707-37-1 C₁₈H₁₃ClN₄O₄ 
• 104707-67-7 5-(5-Nitro-furan-2-yl)-2,4-diphenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 104707-34-8 C₁₈H₁₄N₄O₄ 
• 104707-46-2 5-nitro-2-furaldehyde 2-chloroformyl-2-phenylhydrazone 

Relevant articles and documents

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.

The Reaction of Aniline with 5-Nitro-2-furaldehyde. A Model for Non-Enzymic Browning Reactions

The condensation between 5-nitro-2-furaldehyde and aniline, a model for food browning reactions, yields the corresponding Schiff base, 5-nitro-2-furfurylideneaniline, cleanly.The corresponding reaction with 2-furaldehyde itself yields, in contrast, a mixture of products.Since the equilibrium constant for formation of the Schiff base from 5-nitro-2-furaldehyde and aniline, 177 dm3mol-1, is not large enough to drive the reaction to completion at moderate concentrations of aniline, phenylhydrazine was employed to trap the Schiff base as it was formed: that is, the reaction with aniline was studied by examining aniline-catalysed phenylhydrazone formation.