166179-37-9

Basic information

• Product Name: 3-(CHLOROMETHYL)-5-(4-FLUOROPHENYL)-1,2,4-OXADIAZOLE
• Synonyms: 3-(CHLOROMETHYL)-5-(4-FLUOROPHENYL)-1,2,4-OXADIAZOLE
• CAS NO: 166179-37-9
• Molecular Formula: C₉H₆ClFN₂O
• Molecular Weight: 212.61
• Mol File: 166179-37-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(CHLOROMETHYL)-5-(4-FLUOROPHENYL)-1,2,4-OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CHLOROMETHYL)-5-(4-FLUOROPHENYL)-1,2,4-OXADIAZOLE(166179-37-9)
• EPA Substance Registry System: 3-(CHLOROMETHYL)-5-(4-FLUOROPHENYL)-1,2,4-OXADIAZOLE(166179-37-9)

Safety Data

• Hazardous Substances Data: 166179-37-9(Hazardous Substances Data)

Upstream product

• 166179-36-8 2-chloro-N-((4-fluorobenzoyl)oxy)acetimidamide 
• 403-43-0 4-fluorobenzoyl chloride 
• 3272-96-6 2-chloro-N-hydroxyethanimidamide 
• 166179-36-8 C₉H₈ClFN₂O₂ 

Downstream Products

• 1622982-20-0 C₁₅H₉FN₄OS 
• 1352565-29-7 (R)-1-((5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)methyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate 
• 1026800-76-9 3-[5-(4-fluoro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-benzaldehyde 
• 1027225-19-9 N-{4-[5-(4-fluoro-phenyl)-[1,2,4]oxadiazol-3-ylmethoxy]-benzyl}-hydroxylamine 

Relevant articles and documents

Novel N-Substituted oseltamivir derivatives as potent influenza neuraminidase inhibitors: Design, synthesis, biological evaluation, ADME prediction and molecular docking studies

The discovery of novel potent neuraminidase (NA) inhibitors remains an attractive approach for treating infectious diseases caused by influenza. In this study, we describe the design and synthesis of novel N-substituted oseltamivir derivatives for probing the 150-cavity which is nascent to the activity site of NA. NA inhibitory studies showed that new derivatives demonstrated the inhibitory activity with IC50 values at nM level against NA of a clinical influenza virus strain. Moreover, the in silico ADME predictions showed that the selected compounds had comparable properties with oseltamivir carboxylate, which demonstrated the druggablity of these derivatives. Furthermore, molecular docking studies showed that the most potent compound 6f and 10i could adopt different modes of binding interaction with NA, which may provide novel solutions for treating oseltamivir-resistant influenza. Based on the research results, we consider that compounds 6f and 10i have the potential for further studies as novel antiviral agents.

ALKALOID AMINOESTER DERIVATIVES AND MEDICINAL COMPOSITION THEREOF

The present invention relates to alkaloid aminoester derivatives acting as muscarinic receptor antagonists, processes for their preparation, compositions comprising them and therapeutic uses thereof.

New GABA-modulating 1,2,4-oxadiazole derivatives and their anticonvulsant activity

A series of 3- and 5-aryl-1,2,4-oxadiazole derivatives were prepared and tested for anticonvulsant activity in a variety of models. These 1,2,4-oxadiazoles exhibit considerable activity in both pentylenetetrazole (PTZ) and maximal electroshock seizure (MES) models. Compound 10 was protective in the PTZ model in rats with an oral ED50 of 25.5 mg/kg and in the MES model in rats with an oral ED50 of 14.6 mg/kg. Neurotoxicity (rotarod) was observed with an ED50 of 335 mg/kg. We found several oxadiazoles that acted as selective GABA potentiating compounds with no interaction to the benzodiazepine binding site.

The discovery of a selective, high affinity A2B adenosine receptor antagonist for the potential treatment of asthma

Adenosine has been suggested to play a role in asthma, possibly via activation of A2B adenosine receptors on mast cells and other pulmonary cells. We describe our initial efforts to discover a xanthine based selective A2B AdoR antagonist that resulted in the discovery of CVT-5440, a high affinity A2B AdoR antagonist with good selectivity (A2B AdoR Ki = 50 nM, selectivity A1 > 200: A2A > 200: A3 > 167).

CVT-4325: A potent fatty acid oxidation inhibitor with favorable oral bioavailability

New inhibitors of palmitoyl-CoA oxidation are based on the introduction of nitrogen heterocycles in the 'Western Portion' of the molecule. SAR studies led to the discovery of CVT-4325, a potent FOXi (IC50 = 380 nM, rat mitochondria) with favorable PK properties (F = 93%, t1/2 = 13.6 h, dog). New inhibitors of palmitoyl-CoA oxidation are based on the introduction of nitrogen heterocycles in the 'Western Portion' of the molecule. SAR studies led to the discovery of CVT-4325 (shown), a potent FOXi (IC50 = 380 nM rat mitochondria) with favorable PK properties (F = 93%, t1/2 = 13.6 h, dog).

NEW COMPOUNDS

The present invention relates to new compounds of formula I, (I) a process for their preparation and new intermediates prepared therein, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.