53919-74-7

Basic information

• Product Name: 1,2,4-OXADIAZOLE, 5-(2-CHLOROETHYL)-3-PHENYL
• Synonyms: 1,2,4-OXADIAZOLE, 5-(2-CHLOROETHYL)-3-PHENYL;5-(2-CHLOROETHYL)-3-PHENYL-1,2,4-OXADIAZOLE
• CAS NO: 53919-74-7
• Molecular Formula: C₁₀H₉ClN₂O
• Molecular Weight: 208.64
• Mol File: 53919-74-7.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2,4-OXADIAZOLE, 5-(2-CHLOROETHYL)-3-PHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-OXADIAZOLE, 5-(2-CHLOROETHYL)-3-PHENYL(53919-74-7)
• EPA Substance Registry System: 1,2,4-OXADIAZOLE, 5-(2-CHLOROETHYL)-3-PHENYL(53919-74-7)

Safety Data

• Hazardous Substances Data: 53919-74-7(Hazardous Substances Data)

Usage

Chemical Structure

1,2,4-Oxadiazole ring with a 2-chloroethyl group and a phenyl group

Usage

Commonly used in the synthesis of pharmaceuticals, agrochemicals, and dye stuffs

Biological Activities

Potential antifungal and antimicrobial activities

Derivatives

Shown anti-inflammatory, anticancer, and antiviral properties

Safety

Important to handle with caution and follow proper safety protocols due to potential toxicity and harmful effects if not used correctly

Upstream product

• 10560-64-2 N-[(3-chloropropanoyl)oxy]benzenecarboximidamide 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 625-36-5 2-chloropropionyl chloride 
• 100-47-0 benzonitrile 
• 613-92-3 N-hydroxybenzamidine 
• 10560-64-2 N-[(chloropropionyl)oxy]benzenecarboximidamide 
• 20495-99-2 3-chloropropionic anhydride 
• 613-92-3 N-hydroxyl-benzamidine 
• 10560-64-2 (Z)-N’-(2-chloropropanoyloxy)benzimidamide 
• 542-76-7 3-Chloropropionitrile 

Downstream Products

• 1043537-84-3 isopropyl-[2-(3-phenyl-[1,2,4]oxadiazol-5-yl)ethyl]amine 
• 959-14-8 oxolamine 
• 21891-79-2 N,N-dimethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine 
• 92439-99-1 3-phenyl-5-[2-(pyrrolidin-1-yl)ethyl]-1,2,4-oxadiazole 
• 94090-96-7 1-methyl-4-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]piperazine 
• 92440-21-6 4-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]morpholine 

Relevant articles and documents

Synthesis and Biological Evaluation of Sigma-1 (σ1) Receptor Ligands Based on Phenyl-1,2,4-oxadiazole Derivatives

In this study, a series of phenyl-1,2,4-oxadiazole derivatives were synthesized and evaluated for anti-allodynic activity. Structure–activity relationship studies identified 1-{4-[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl]butyl}piperidine (39) with excellent affinity for the σ1 receptor and selectivity for the σ2 receptor, with poor activity to other central nervous system neurotransmitter receptors and transporters associated with pain. Compound 39 exhibited dose-dependent efficacy in suppressing the formalin-induced flinching and attenuating mechanical allodynia in chronic constriction injury-induced neuropathic rats. These results suggest that compound 39 exerts potent antihyperalgesic activity and could be considered as a promising candidate for treating neuropathic pain.

Discovery of novel heteroarylmethylcarbamodithioates as potent anticancer agents: Synthesis, structure-activity relationship analysis and biological evaluation

A series of new analogs based on the structure of lead compound 10 were designed, synthesized and evaluated for their in vitro anti-cancer activities against four selected human cancer cell lines (HL-60, Bel-7402, SK-BR-3 and MDA-MB-468). Several synthesized compounds exhibited improved anti-cancer activities comparing with lead compound 10. Among them, 1,3,4-oxadiazole analogs 17o showed highest bioactivity with IC50 values of 1.23, 0.58 and 4.29 μM against Bel-7402, SK-BR-3 and MDA-MB-468 cells, respectively. It is noteworthy that 17o has potent anti-proliferation activity toward a panel of cancer cells with relatively less cytotoxicity to nonmalignant cells. The further mechanistic study showed that it induced apoptosis and cell cycle arrest through disrupting spindle assembly in mitotic progression, indicating these synthesized dithiocarbamates represented a novel series of anti-cancer compounds targeting mitosis.

Efficient and convenient protocol for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using HClO4-SiO2 as a heterogeneous recyclable catalyst

Silica-supported perchloric acid (HClO4SiO2) was found to be a new, highly efficient, inexpensive, and reusable catalyst for a rapid and efficient synthesis of various 1,2,4-oxadiazoles with good to excellent yields under solvent-free conditions. The present methodology has been effectively utilized for the synthesis of oxolamine, an anti-inflammatory drug.