95124-68-8

Usage

Uses

Used in Medicinal Chemistry:
4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BENZOIC ACID is used as a potential scaffold for drug development due to its distinctive structural features. Its 1,2,4-oxadiazole ring provides opportunities for the design of new pharmaceutical agents with improved pharmacological properties, such as enhanced bioavailability, selectivity, and potency.
Used in Materials Science:
In the field of materials science, 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BENZOIC ACID may be utilized as a component in the development of novel materials with specific properties. Its incorporation into polymers or other materials could lead to advancements in areas such as electronics, coatings, or sensors, where its electronic and structural characteristics could be advantageous.
Used in Organic Synthesis:
4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BENZOIC ACID serves as a valuable intermediate in organic synthesis. Its reactivity and functional group compatibility make it a versatile building block for the synthesis of more complex organic molecules, which could have applications in pharmaceuticals, agrochemicals, or other specialty chemicals.
Further studies on the properties and reactions of 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BENZOIC ACID are essential to fully explore and understand its potential applications across different scientific disciplines.

InChI:InChI=1/C10H8N2O3/c1-6-11-9(12-15-6)7-2-4-8(5-3-7)10(13)14/h2-5H,1H3,(H,13,14)

Upstream product

• 23610-05-1 4-(N-hydroxycarbamimidoyl)-benzoic acid 
• 619-66-9 4-Carboxybenzaldehyde 
• 64-19-7 acetic acid 
• 196301-94-7 methyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 108-24-7 acetic anhydride 
• 619-65-8 4-cyanobenzoic Acid 
• 65695-05-8 methyl 4-(N’-hydroxycarbamimidoyl)benzoate 
• 81386-30-3 5-methyl-3-(4-methylphenyl)-1,2,4-oxadiazole 
• 184778-33-4 4-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester 
• 184778-33-4 methyl (Z)-4-(N’-hydroxycarbamimidoyl)benzoate 

Downstream Products

• 222541-76-6 4-(5-methyl-1,2,4-oxadiazol-3-yl)-benzoyl chloride 
• 1449701-94-3 4-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoyl azide 
• 49787-02-2 4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol 
• 340736-46-1 methyl 2-[(2S)-4-[2-(tert-butoxy)-2-oxoethyl]-1-[(2S)-3-(4-methoxyphenyl)-2-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)benzoyl]amino]propanoyl]-3-oxopiperazinyl]acetate 

Relevant academic research and scientific papers

Evaluation of 5-(Trifluoromethyl)-1,2,4-oxadiazole-Based Class IIa HDAC Inhibitors for Huntington's Disease

Using an iterative structure-activity relationship driven approach, we identified a CNS-penetrant 5-(trifluoromethyl)-1,2,4-oxadiazole (TFMO, 12) with a pharmacokinetic profile suitable for probing class IIa histone deacetylase (HDAC) inhibition in vivo.

Synthesis, Antifungal Activity, DFT Study and Molecular Dynamics Simulation of Novel 4-(1,2,4-Oxadiazol-3-yl)-N-(4-phenoxyphenyl)benzamide Derivatives

In order to find novel potential antifungal agrochemicals, a series of new 4-(1,2,4-oxadiazol-3-yl)-N-(4-phenoxyphenyl)benzamide derivatives 3a–j were designed, synthesized and characterized by their 1H-, 13C-NMR and HRMS spectra. Th

Synthesis of benzoic acids containing a 1,2,4-oxadiazole ring

A new approach to the synthesis of 4and 3-(5-R-1,2,4-oxadiazol-3-yl)benzoic acids via a selective oxidation of 5-R-3-tolyl-1,2,4-oxadiazoles with air oxygen in the presence of a catalytic system based on cobalt acetate was suggested. This synthesis allowed us to obtain the products in higher yields and with shorter sequence of steps as compared to the known procedures.

MODULATORS OF ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTORS AND THERAPEUTIC USES THEREOF

The present invention relates to compounds with α7 nAChR agonistic activity, processes for their preparation, pharmaceutical compositions containing the same and the use thereof for the treatment of neurological, psychiatric, cognitive, immunological and inflammatory disorders.

Orally active GPIIb/IIIa antagonists: Synthesis and biological activities of masked amidines as prodrugs of 2-[(3S)-4-[(2S)-2-(4-amidinobenzoylamino)-3-(4-methoxyphenyl)propanoyl]-3- (2-methoxy-2-oxoethyl)-2-oxopiperazinyl]acetic acid

To improve the in vivo potency of the potent GPIIb/IIIa antagonist 2-[(3S)-4-[(2S)-2-(4-amidinobenzoylamino)-3-(4-methoxyphenyl)propanoyl]-3- (2-methoxy-2-oxoethyl)-2-oxopiperazinyl]lacetic acid (4), the amidino group was converted to an oxadiazole ring, thiadiazole ring of substituted amidoxime group. These groups were expected to be metabolized to an amidino group in vivo. The compounds synthesized were evaluated for their potency to inhibit the ex vivo adenosine 5′-diphosphate (ADP)-induced aggregation of guinea pig platelets. Among the compounds examined, the methoxycarbonyloxyamidine 8a exhibited the most potent ex vivo inhibitory activity with a fast onset and prolonged duration of action after oral administration.

Direct Synthesis of 5-Methyl-3-aryl-1,2,4-oxadiazoles from Aryl Aldehydes, Nitroethane, and Ammonium Acetate

The condensation of 2,5-dimethoxybenzaldehyde (1b) with nitroethane and ammonium acetate in glacial acetic acid has been found to give three diffrent products, depending on reactant ratio and reaction time.At an aldehyde:nitroethane:ammonium acetate ratio of 1:1.5:0.8 a normal Knoevenagel condensation occured, yielding 1-(2,5-dimethoxyphenyl)-2-nitropropene.At a reactant ratio of 1:3:2 (same reactant sequence), the primary product was 2,5-dimethoxybenzonitrile, and at a reactant ratio of 1:40:8, with extended reflux time, the major product was 3-(2,5-dimethoxyphenyl)-5-methyl-1,2,4-oxadiazole (8b).This last reaction served as a prototype for a new oxadiazole synthesis which was then extended to include six additional 5-methyl-3-aryl-1,2,4-oxadiazoles (8a,c-g; where aryl = Ph, 2,5-dimethoxyphenyl, 2,4-dichlorophenyl, m-chlorophenyl, p-tolyl, 3,5-dimethoxyphenyl, and p-carboxyphenyl), whose structures were assigned on the basis of 13C NMR characteristics of known reference compounds.Benzonitrile also reacted with excess nitroethane and ammonium acetate to yield 5-methyl-3-phenyl-1,2,4-oxadiazole (8a).The overall mechanism of oxadiazole formation is shown to be dependent on a preliminary reaction wherein the nitroalkane, in the presence of ammonium acetate and acetic acid, is first transformed into the corresponding alkanoic acid and hydroxylamine.Hydroxylamine then converts the aromatic aldehyde, via the intermediary nitrile, to the oxadiazoles following reactions of established precedent.