153708-69-1

Basic information

• Product Name: 1-(3,5-DICHLORO-4-PYRIDYL)HYDRAZINE
• Synonyms: 1-(3,5-DICHLORO-4-PYRIDYL)HYDRAZINE;BUTTPARK 91\18-52;1-(3,5-Dichloropyridin-4-yl)hydrazine;Pyridine,3,5-dichloro-4-hydrazino-(9CI);3,5-DICHLOROPYRIDIN-4-YLHYDRAZINE;3,5-Dichloro-4-hydrazinopyridine;(3,5-Dichloropyrdin-4-yl)hydrazine
• CAS NO: 153708-69-1
• Molecular Formula: C₅H₅Cl₂N₃
• Molecular Weight: 178.02
• Product Categories: HYDRAZINE
• Mol File: 153708-69-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 113-115°C
• Boiling Point: 264.3°Cat760mmHg
• Flash Point: 113.6°C
• Appearance: /
• Density: 1.572g/cm³
• Vapor Pressure: 0.00978mmHg at 25°C
• Refractive Index: 1.677
• PKA: 3.10±0.33(Predicted)
• CAS DataBase Reference: 1-(3,5-DICHLORO-4-PYRIDYL)HYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-DICHLORO-4-PYRIDYL)HYDRAZINE(153708-69-1)
• EPA Substance Registry System: 1-(3,5-DICHLORO-4-PYRIDYL)HYDRAZINE(153708-69-1)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• Hazardous Substances Data: 153708-69-1(Hazardous Substances Data)

Usage

General Description

1-(3,5-Dichloro-4-pyridyl)hydrazine is a chemical compound with the formula C5H5Cl2N3. It is a hydrazine derivative that is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. 1-(3,5-DICHLORO-4-PYRIDYL)HYDRAZINE is known for its biological activity and has been extensively studied for its potential applications in the treatment of cancer and other diseases. It is also used as a pesticide and is known to exhibit herbicidal properties. 1-(3,5-Dichloro-4-pyridyl)hydrazine is considered to be a potentially hazardous chemical and should be handled and stored with caution.

InChI:InChI=1/C5H5Cl2N3/c6-3-1-9-2-4(7)5(3)10-8/h1-2H,8H2,(H,9,10)

Upstream product

• 343781-41-9 3,5-dichloro-4-iodopyridine 
• 33216-52-3 3,4,5-trichloropyridine 

Downstream Products

• 1370286-97-7 N-benzyl-2-(3,5-dichloropyridin-4-yl)hydrazinecarboxamide 
• 1370286-80-8 N'-(3,5-dichloropyridin-4-yl)-N-methyl-3-phenylpropanehydrazide 
• 1370286-87-5 2-(4-chlorophenyl)-N'-(3,5-dichloropyridin-4-yl)acetohydrazide 
• 1370286-92-2 N'-(3,5-dichloropyridin-4-yl)-2-phenylacetohydrazide 
• 1370286-83-1 N'-(3,5-dichloropyridin-4-yl)-3-(4-fluorophenyl)propanehydrazide 
• 1370286-98-8 (E)-N'-(3,5-dichloropyridin-4-yl)cinnamoylhydrazide 
• 1370286-84-2 3-(4-chlorophenyl)-N'-(3,5-dichloropyridin-4-yl)propanehydrazide 
• 1370286-88-6 2-(2,4-dichlorophenyl)-N'-(3,5-dichloropyridin-4-yl)-acetohydrazide 
• 1370286-94-4 N'-(3,5-dichloropyridin-4-yl)-6-phenylhexanehydrazide 
• 1370286-86-4 N'-(3,5-dichloropyridin-4-yl)-3-(4-methoxyphenyl)propanehydrazide 
• 1370286-95-5 N'-(3,5-dichloropyridin-4-yl)-7-phenylheptanehydrazide 
• 1370287-09-4 2-cyclohexyl-N'-(3,5-dichloropyridin-4-yl)acetohydrazide 
• 1370287-10-7 4-cyclohexyl-N'-(3,5-dichloropyridin-4-yl)butanehydrazide 
• 1370287-07-2 3-cyclohexyl-N'-(3,5-dichloropyridin-4-yl)propanehydrazide 

Relevant articles and documents

Nanoparticle-encapsulated P2X7 receptor antagonist in a pH-sensitive polymer as a potential local drug delivery system to acidic inflammatory environments

We have developed nanoparticles of anti-inflammatory P2X7 receptor antagonist encapsulated in a pH-sensitive polymer, poly(tetrahydropyran-2-yl methacrylate) (poly(THPMA)), as a potential local drug delivery system to target to acidic inflammatory environments, in which P2X7 receptors are implicated in the pathology of inflammation via the activation of immune cells. The nanoparticles were prepared using single emulsion methods, also their size and shape were confirmed by microscopy and spectroscopy, etc. The profiles of the pH-dependent degradation, release of antagonist and biological activities were investigated. The nanoparticles that encapsulated the 3,5-dichloropyridine derivative (2) with poly(THPMA), were observed to be more slowly cleaved than the blank nanoparticles. Moreover, the free P2X7 receptor antagonists potently inhibited the receptor activation, whereas the nanoparticles of the 3,5-dichloropyridine derivative (2) encapsulated poly(THPMA) exhibited much lower P2X7 antagonistic activity through sustained encapsulation. Thus, the nanoparticles of the 3,5-dichloropyridine derivative (2) encapsulated poly(THPMA) may be utilized to develop a pH-sensitive local drug delivery system for controlled release of anti-inflammatory therapeutics in acidic physiological environments.

Structure-activity relationships and optimization of 3,5-dichloropyridine derivatives as novel P2X7 receptor antagonists

Screening of a library of chemical compounds showed that the dichloropyridine-based analogue 9 was a novel P2X7 receptor antagonist. To optimize its activity, we assessed the structure-activity relationships (SAR) of 9, focusing on the hydrazide linker, the dichloropyridine skeleton, and the hydrophobic acyl (R2) group. We found that the hydrazide linker and the 3,5-disubstituted chlorides in the pyridine skeleton were critical for P2X7 antagonistic activity and that the presence of hydrophobic polycycloalkyl groups at the R2 position optimized antagonistic activity. In the EtBr uptake assay in hP2X7-expressing HEK293 cells, the optimized antagonists, 51 and 52, had IC50 values of 4.9 and 13 nM, respectively. The antagonistic effects of 51 and 52 were paralleled by their ability to inhibit the release of the pro-inflammatory cytokine, IL-1β, by LPS/IFN-γ/BzATP stimulation of THP-1 cells (IC50 = 1.3 and 9.2 nM, respectively). In addition, 52 strongly inhibited iNOS/COX-2 expression and NO production in THP-1 cells, further indicating that this compound blocks inflammatory signaling and suggesting that the dichloropyridine analogues may be useful in developing P2X7 receptor targeted anti-inflammatory agents.