500025-07-0

Basic information

• Product Name: 3-[3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL]PROPANOIC ACID
• Synonyms: BUTTPARK 85\04-45;AKOS BB-7077;3-[3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL]PROPANOIC ACID;ZERENEX E/5111169;1,2,4-oxadiazole-5-propanoic acid, 3-(4-fluorophenyl)-;3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]propionic acid;ZERO/009511
• CAS NO: 500025-07-0
• Molecular Formula: C₁₁H₉FN₂O₃
• Molecular Weight: 236.2
• Mol File: 500025-07-0.mol

Chemical Properties

• Melting Point: 146-147 °C(Solv: chloroform (67-66-3))
• Boiling Point: 426.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.372±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.06±0.10(Predicted)
• CAS DataBase Reference: 3-[3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL]PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL]PROPANOIC ACID(500025-07-0)
• EPA Substance Registry System: 3-[3-(4-FLUOROPHENYL)-1,2,4-OXADIAZOL-5-YL]PROPANOIC ACID(500025-07-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 500025-07-0(Hazardous Substances Data)

Upstream product

• 1194-02-1 4-fluorobenzonitrile 
• 108-30-5 succinic acid anhydride 
• 22179-78-8 4-fluoro-benzamidoxime 

Downstream Products

• 1051372-24-7 N-(9-ethyl-9H-carbazol-3-yl)-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)propanamide 

Relevant articles and documents

Development of fluorinated CB2 receptor agonists for PET studies

A convergent strategy was followed to modify systematically carbazole based CB2 receptor ligands. The length of the N-(fluoroalkyl) group (n in 7), the length of the alkanamide (m in 7) and the substitution pattern of the phenyl moiety (X and Y in 7) were varied systematically. The highest CB 2 affinity was found for the 2-fluoroethyl substituted carbazole derivative 20a (Ki = 5.8 nM) containing the propionamide and the 2-bromo-4-fluorophenyl moiety. According to docking studies 20a fits nicely into the binding pocket of the CB2 receptor, but elongation of the fluoroethyl side chain leads to a different binding mode of the ligands. The high CB2 affinity together with the high selectivity over the CB 2 subtype qualifies the fluoroethyl derivative 20a to be developed as a PET tracer.

Discovery and optimization of a novel series of N-arylamide oxadiazoles as potent, highly selective and orally bioavailable cannabinoid receptor 2 (CB 2) agonists

The CB2 receptor is an attractive therapeutic target for analgesic and anti-inflammatory agents. Herein we describe the discovery of a novel class of oxadiazole derivatives from which potent and selective CB 2 agonist leads were developed. Initial hit 7 was identified from a cannabinoid target-biased library generated by virtual screening of sample collections using a pharmacophore model in combination with a series of physicochemical filters. 7 was demonstrated to be a selective CB2 agonist (CB2 EC50 = 93 nM, Emax = 98%, CB 1 EC50 > 10 μM). However, this compound exhibited poor solubility and relatively high clearance in rat, resulting in low oral bioavailability. In this paper, we report detailed SAR studies on 7 en route toward improving potency, physicochemical properties, and solubility. This effort resulted in identification of 63 that is a potent and selective agonist at CB2 (EC50 = 2 nM, Emax = 110%) with excellent pharmacokinetic properties.