24088-59-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-Phenyl-1,2,4-oxadiazol-5-yl)propanoate is used as a reactant for the preparation of N-arylamide oxadiazoles, which are selective oral CB2 agonists. These agonists have potential therapeutic applications in various medical conditions, including pain management, inflammation, and neurodegenerative diseases. The compound's reactivity and structural features make it a valuable building block in the synthesis of these pharmaceutical agents.

InChI:InChI=1/C11H10N2O3/c14-10(15)7-6-9-12-11(13-16-9)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,14,15)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 613-92-3 N-hydroxyl-benzamidine 
• 155500-79-1 C₁₂H₁₂N₂O₃ 
• 1175001-94-1 4-(((amino(phenyl)methylene)amino)oxy)-4-oxobutanoic acid 
• 100-47-0 benzonitrile 

Downstream Products

• 433717-33-0 3-(phenyl-1,2,4-oxadiazol-5-yl)propionyl chloride 
• 172678-75-0 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanol 
• 322723-65-9 N-(9-ethyl-9H-carbazol-3-yl)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanamide 
• 1187182-65-5 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propionic acid prop-2-ynyl ester 

Relevant academic research and scientific papers

A handy and solventless direct route to primary 3-[3-aryl-1,2,4-oxadiazol- 5-yl]propionamides using microwave irradiation

A one-step, simple and straightforward synthesis of the title amides from the corresponding carboxylic acids, urea and imidazole under microwave irradiation is described.

Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety

An efficient and mild one-pot protocol has been developed for the synthesis of 1,2,4-oxadiazoles via the reaction of amidoximes with dicarboxylic acid anhydrides in a NaOH/DMSO medium. The method allows the synthesis of diversely substituted carboxylic acids bearing the 1,2,4-oxadiazole motif, – a popular building block for pharmaceutical research, in moderate to excellent yields. The reaction scope includes aromatic and heteroaromatic amidoximes as well as five-, six- and seven-membered anhydrides. The advantages of this procedure are proven gram-scalability and the use of inexpensive starting materials, which from a process chemistry point of view are essential for future industrial applications.

Improved microwave-mediated synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl) propionic acids and their larvicidal and fungal growth inhibitory properties

The synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids from arylamidoximes and succinic anhydride under focused microwave irradiation conditions is described. The new synthetic method furnished the desired products in 2-3 min and good yields. Fur

Synthesis, characterization, and antimicrobial activities of clubbed [1,2,4]-oxadiazoles with fluorobenzimidazoles

(Chemical Equation Presented) In this study, a novel series of substituted 4,6-difluoro-2-{2-[3-(substituted-phenyl)-[1,2,4]-oxadiazol-5-yl]-ethyl} -1H-benzo[d]imidazole derivatives were synthesized by condensation of 2,4-difluoro-6-nitrophenyl amine with 3-(substitutedphenyl-[1,2,4]-oxadiazol- 5yl) propionic acid by using 2,4,6-trichlorobenzoyl chloride in the presence of triethyl amine base. The compounds were evaluated for their preliminary in vitro antibacterial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, and Salmonella typhosa. The antibacterial data of the tested compounds indicated that most of the synthesized compounds showed moderate activity with reference standard Gentamycin.

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.

DISUBSTITUTED THIENYL COMPOUNDS AND THEIR USE AS PHARMACEUTICALS

The present invention relates to modulators of HM74a receptor, and pharmaceutical compositions thereof. The compounds of the invention can be useful in the treatment of various diseases associated with HM74a receptor.

Synthesis and structure determination of N,N-diethyl-3-[3-aryl-1,2,4- oxadiazol-5-yl]propionamides

An efficient and facile synthesis of six new 1,2,4-oxadiazoles (6a-f) with a tertiary amide group attached on the side-chain, in high yield, is described. Correct assignments of side-chain methylene, methyl protons, and carbon signals have been made with the assistance of COSY, NOESY and HETCOR NMR experiments.