28825-12-9

Upstream product

• 100-47-0 benzonitrile 
• 619-80-7 4-nitrobenzamide 
• 62-23-7 4-nitro-benzoic acid 
• 80366-00-3 C₁₄H₁₁N₃O₃ 
• 613-92-3 N-hydroxyl-benzamidine 
• 122-04-3 4-nitro-benzoyl chloride 
• 132353-24-3 4-Nitro-benzoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 109-92-2 ethyl vinyl ether 
• 188118-32-3 5-(4-Nitro-phenyl)-3-phenyl-[1,2,4]oxadiazole 4-oxide 
• 188118-39-0 N,N-Diethyl-N'-hydroxy-4-nitro-benzamidine 
• 1011-84-3 4-nitrobenzohydroximoyl chloride 
• 968-09-2 C₁₄H₁₁N₃O₄ 
• 934-16-7 phenylhydroxamoyl chloride 

Downstream Products

• 902318-46-1 4-nitro-N-(4-(3-phenyl-1,2,4-oxadiazole-5-yl)phenyl)benzamide 
• 931755-63-4 4-methoxy-N-(4-(3-phenyl-1,2,4-oxadiazole-5-yl)phenyl)-benzamide 
• 931325-39-2 4-methyl-N-(4-(3-phenyl-1,2,4-oxadiazole-5-yl)phenyl)benzamide 
• 1092342-60-3 4-chloro-N-(4-(3-phenyl-1,2,4-oxadiazole-5-yl)phenyl)benzamide 
• 1223811-01-5 4-fluoro-N-(4-(3-phenyl-1,2,4-oxadiazole-5-yl)phenyl)benzamide 
• 902306-92-7 N-(4-(3-phenyl-1,2,4-oxadiazole-5-yl)phenyl)benzamide 
• 54494-12-1 5-(4'-aminophenyl)-3-phenyl-1,2,4-oxadiazole 

Relevant academic research and scientific papers

An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage

A high-yielding method for the synthesis of 2 H -1,3,5-oxadiazines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadiazoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.

New 1,2,4-oxadiazole derivatives with positive mGlu4 receptor modulation activity and antipsychotic-like properties

Considering the allosteric regulation of mGlu receptors for potential therapeutic applications, we developed a group of 1,2,4-oxadiazole derivatives that displayed mGlu4 receptor positive allosteric modulatory activity (EC50 = 282–656 nM). Selectivity screening revealed that they were devoid of activity at mGlu1, mGlu2 and mGlu5 receptors, but modulated mGlu7 and mGlu8 receptors, thus were classified as group III-preferring mGlu receptor agents. None of the compounds was active towards hERG channels or in the mini-AMES test. The most potent in?vitro mGlu4 PAM derivative 52 (N-(3-chloro-4-(5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl)phenyl)picolinamide) was readily absorbed after i.p. administration (male Albino Swiss mice) and reached a maximum brain concentration of 949.76 ng/mL. Five modulators (34, 37, 52, 60 and 62) demonstrated significant anxiolytic- and antipsychotic-like properties in the SIH and DOI-induced head twitch test, respectively. Promising data were obtained, especially for N-(4-(5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)picolinamide (62), whose effects in the DOI-induced head twitch test were comparable to those of clozapine and better than those reported for the selective mGlu4 PAM ADX88178.

1,2,4-oxadiazole derivatives as allosteric modulators of metabotropic glutamate receptors belonging to group III

The present invention relates to the novel 1,2,4-oxadiazole derivatives of general Formula I, wherein A, B, M, X, Y, R 1 , R 2 and R 3 are defined in the application. The compounds of the invention are modulators of metabotropic glutamate receptors that b

Copper-catalyzed direct synthesis of 1,2,4-oxadiazoles from amides and organic nitriles by oxidative N-O bond formation

Herein, we report the first Cu-catalyzed one-step method for the synthesis of 1,2,4-oxadiazoles from stable, less toxic, and readily available amides and organic nitriles by a rare oxidative N-O bond formation using O2 as sole oxidant. This met

One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acids using 4-(dimethylamino)pyridinium acetate as efficient, regenerable, and green catalyst with ionic liquid character

A recyclable bifunctional acid-base organocatalyst with ionic liquid character has been prepared and its catalytic activity for the preparation of oxadiazoles has been investigated.

A metal-free tandem approach to prepare structurally diverse N-heterocycles: Synthesis of 1,2,4-oxadiazoles and pyrimidinones

A metal-free one-pot approach to the diversity oriented synthesis of N-heterocycles, 1,2,4-oxadiazoles and 2,6 disubstituted pyrimidin-4-ones is described via carboxamidation of amidines with aryl carboxylic acids and aryl propargylic acids. The reactions occur at room temperature forming N-acylamidines which undergo tandem nucleophilic addition-deamination- intramolecular cyclisation to give the corresponding heterocyclic compounds in good to excellent yields. This one pot approach has led to the successful synthesis of the drug lead molecule, ataluren, 3-(5-(2-fluorophenyl)-1,2,4- oxadiazol-3-yl) benzoic acid in two steps. the Partner Organisations 2014.

Design, synthesis and biological evaluation of some oxadiazole derivatives as novel amide-based inhibitors of soluble epoxide hydrolase

Soluble epoxide hydrolase (sEH) enzyme plays an important role in the metabolism of endogenous chemical mediators which are involved in the regulation of blood pressure and inflammation. Although the most reported potent sEH inhibitors are urea derivatives, these compounds have limited pharmacokinetic profile. In order to improve physicochemical properties, besides having favorable potency, amide non-urea derivatives with oxadiazole ring as a novel secondary pharmacophore against sEH enzyme were developed. Most of the novel compounds with appropriate physical properties, had comparable in vitro sEH inhibitory activity to 12-(3-Adamantan-1-yl-ureido)-dodecanoic acid (AUDA), a potent urea-based sEH inhibitor. The IC50value of the most potent compound (15c) was 0.43 nM.

Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 ± 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 ± 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure.

A simple and straightforward protocol to 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids

A convenient one-pot synthesis of 1,2,4-oxadiazoles is described. The condensation of carboxylic acids and amidoximes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NM1 B) has been employed to synthesize a variety of 3,5-disubstituted 1,2,4-oxadiazoles in good to excellent yields. The methodology has been applied for the synthesis of a metabotropic glutamate subtype 5 (mGlu5) receptor antagonist.

1,2,4-Oxadiazole 4-oxides as nitrones in 1,3-dipolar cycloaddition reactions to vinyl ethers

1,2,4-Oxadiazole 4-oxides display nitronic reactivity and selectivities identical to those of N-methyl-C-phenyl nitrone, which is a typical acyclic nitrone, affording comparable amounts of endo- and exo-5-alkoxyisoxazolidines. The exo stereoisomers undergo an easy rearrangement under the reaction conditions to yield oxadiazolinic esters. The structures of the adducts have been confirmed by X-ray structures and spectroscopic data. A donor p-methoxyphenyl at the nitronic carbon slows down the cycloaddition rate, while an acceptor p-nitrophenyl retards the rearrangement of the exo adduct. 1,2,4-Oxadiazole 4-oxides undergo 1,3-dipolar cycloaddition reactions with vinyl ethers to afford endo adducts and labile exo adducts that rearrange to oxadiazolinicesters. The structures of the isolated products were assigned on the basis of spectroscopic data and X-ray analyses. Copyright