6206-85-5

Basic information

• Product Name: (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole
• CAS NO: 6206-85-5
• Molecular Formula: C₉H₈N₄O
• Molecular Weight: 188.186
• Mol File: 6206-85-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 255.7°C at 760 mmHg
• Flash Point: 108.5°C
• Density: 1.31g/cm³
• Vapor Pressure: 0.016mmHg at 25°C
• Refractive Index: 1.663
• CAS DataBase Reference: (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole(6206-85-5)
• EPA Substance Registry System: (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole(6206-85-5)

Safety Data

• Hazardous Substances Data: 6206-85-5(Hazardous Substances Data)

Usage

Description

(5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole is a chemical compound belonging to the triazole family, characterized by a molecular formula of C9H8N4O. (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole features a nitrosomethylidene group attached to the 5th position of the triazole ring, which contributes to its unique structure and reactivity. Its potential pharmacological and biological activities have made it a subject of interest for drug development and medicinal chemistry research.

Uses

Used in Pharmaceutical Research:
(5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole is used as a drug candidate for exploring its potential therapeutic applications. Its unique structure and reactivity make it a promising starting point for the development of new medications targeting various diseases and conditions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole serves as a valuable compound for further research and development. Its properties can be harnessed to design and synthesize novel molecules with improved pharmacological profiles, potentially leading to the discovery of new drugs with enhanced efficacy and safety profiles.
Used in Drug Discovery:
(5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole is utilized in drug discovery processes to identify new molecular targets and develop innovative therapeutic strategies. Its unique chemical structure allows for the exploration of various biological pathways and mechanisms, which could lead to the creation of novel drugs with specific and effective actions against targeted diseases.
Used in Chemical Synthesis:
As a triazole derivative with a nitrosomethylidene group, (5E)-5-(nitrosomethylidene)-2-phenyl-2,5-dihydro-1H-1,2,3-triazole can be employed in chemical synthesis to create a variety of new compounds with diverse applications. Its reactivity and structural features make it a versatile building block for the development of new molecules with potential uses in various industries, including pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 3213-80-7 2-phenyl-1,2,3-triazole-4-carboxaldehyde 
• 100-63-0 phenylhydrazine 
• 534-97-4 glucosazone 
• 6341-06-6 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole 

Downstream Products

• 3213-80-7 2-phenyl-1,2,3-triazole-4-carboxaldehyde 
• 36386-83-1 2-phenyl-1,2,3-triazole-4-carbonitrile 
• 765306-42-1 α-chloro-2-phenyl-2H-[1,2,3]triazole-4-formaldehyde oxime 

Relevant articles and documents

1-Aryl-1H- and 2-aryl-2H-1,2,3-triazole derivatives blockade P2X7 receptor in?vitro and inflammatory response in?vivo

Fifty-one 1,2,3-triazole derivatives were synthesized and evaluated with respect to P2X7 receptor (P2X7R) activity and its associated pore. These triazoles were screened in vitro for dye uptake assay and its cytotoxicity against mammalian cell types. Seven 1,2,3-triazole derivatives (5e, 6e, 8h, 9d, 9i, 11, and 12) potently blocked P2X7 receptor pore formation in vitro (J774.G8 cells and peritoneal macrophages). All blockers displayed IC50 value inferior to 500 nM, and they have low toxicity in either cell types. These seven selected triazoles inhibited P2X7R mediated interleukin-1 (IL-1β) release. In particular, compound 9d was the most potent P2X7R blocker. Additionally, in mouse acute models of inflammatory responses induced by ATP or carrageenan administration in the paw, compound 9d promoted a potent blocking response. Similarly, 9d also reduced mouse LPS-induced pleurisy cellularity. In silico predictions indicate this molecule appropriate to develop an anti-inflammatory agent when it was compared to commercial analogs. Electrophysiological studies suggest a competitive mechanism of action of 9d to block P2X7 receptor. Molecular docking was performed on the ATP binding site in order to observe the preferential interaction pose, indicating that binding mode of the 9d is by interacting its 1,2,3-triazole and ether moiety with positively charged residues and with its chlorobenzene moiety orientated toward the apolar end of the ATP binding site which are mainly composed by the Ile170, Trp167 and Leu309 residues from α subunit. These results highlight 9d derivative as a drug candidate with potential therapeutic application based on P2X7 receptor blockade.

Synthesis of new heterocyclic compounds having 1,2,3-triazole and isoxazole rings in a single molecule

(Chemical Equation Presented) Five series of new heterocyclic compounds of 1,2,4-triazole Mannich bases, 1,3,4-oxadiazole Mannich bases, 1,3,4-oxadiazolines, 1,2,4-triazolo[3,4-b]1,3,4-thiadiazines and 1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles, in which 1,2

6-(SUBSTITUTED)METHYLENE-PENICILLANIC AND 6-(SUBSTITUTED)HYDROXYMETHYL-PENICILLANIC ACIDS AND DERIVATIVES THEREOF

Beta-lactamase inhibiting compounds of the formula: or a pharmaceutically acceptable acid addition or carboxylate salt thereof; where n is zero, 1 or 2; X.3 is H or Br, R1 is H, the residue of certain carboxy-protecting groups or the residue of an ester group readily hydrolyzable in vivo; one of R12 and R13 is H and the other is vinyl, certain aryl, alkylthio, alkylsulfonyl or certain heterocyclyl, aminomethyl, thiocarboxamido or amidino groups; one or R2 and R3 is H and the other is as disclosed for the other of R12 and R13, or is Cl or CH2 OH, and R18 is H or certain acyl groups; intermediates useful in their production, methods for their preparation and use, and pharmaceutical compositions containing them