Production Method 1

81386-30-3

95124-68-8

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cobalt diacetate ,  Sodium bromide Solvents: Acetic acid ;  11 h, 95 °C

Reference

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

Krasouskaya, G. G.; Danilova, A. S.; Baikov, S. V.; Kolobov, A. V.; Kofanov, E. R., Russian Chemical Bulletin, 2015, 64(1), 142-145

Production Method 2

19227-13-5

95124-68-8

Reaction Conditions

1.1 rt → 120 °C; 4 h, 120 °C; cooled
1.2 Reagents: Oxygen Catalysts: Cobalt diacetate ,  Sodium bromide Solvents: Acetic acid ;  11 h, 95 °C

Reference

One-pot synthesis of (5-alkyl-1,2,4-oxadiazol-3-yl)benzoic acids

Baikov, Sergei V.; Krasovskaya, Galina G.; Kolobov, Aleksei V.; Kofanov, Evgenii R., Mendeleev Communications, 2015, 25(2), 138-139

Production Method 3

95124-68-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Hydroxylamine Solvents: Dimethylformamide ,  Tetrahydrofuran ;  2 h, reflux
1.2 0.5 h, reflux

Reference

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

Yang, Zihui ; Liu, Qingsong; Sun, Yue; Sun, Xuebao; Chen, Linlin; et al, Chemistry & Biodiversity, 2021, 18(12),

Production Method 4

196301-94-7

95124-68-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol
1.2 Reagents: Hydrochloric acid

Reference

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

Kitamura, Shuji; Fukushi, Hideto; Miyawaki, Toshio; Kawamura, Masaki; Terashita, Zen-Ichi; et al, Chemical & Pharmaceutical Bulletin, 2001, 49(3), 268-277

Production Method 5

619-66-9

95124-68-8

Reaction Conditions

1.1 Reagents: Acetic acid

Reference

Direct synthesis of 5-methyl-3-aryl-1,2,4-oxadiazoles from aryl aldehydes, nitroethane, and ammonium acetate

Young, Thomas E.; Beidler, William Thomas, Journal of Organic Chemistry, 1985, 50(8), 1182-6

Production Method 6

95124-68-8

Reaction Conditions

Reference

Preparation of 4-heterocyclylbutanamide derivatives as modulators of alpha 7 nicotinic acetylcholine receptors

, World Intellectual Property Organization, , ,

Production Method 7

95124-68-8

Reaction Conditions

Reference

Benzamide derivatives and cell adhesion inhibitors containing them

, Japan, , ,

4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid Raw materials

• 5-Methyl-3-(p-tolyl)-1,2,4-oxadiazole
• 4-Carboxybenzaldehyde
• Methyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate
• N'-Hydroxy-4-methylbenzenecarboximidamide

4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid Preparation Products

• 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid (95124-68-8)

• 1. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156
• 2. An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening
  Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai Kong Analyst, 2017,142, 3579-3587
• 3. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 4. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
• 5. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Oxadiazoles 1,2,4-oxadiazoles
• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds

Recent Advances in the Study of 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid (CAS: 95124-68-8)

4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid (CAS: 95124-68-8) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its unique structural features and potential therapeutic applications. Recent studies have explored its role as a versatile scaffold for drug discovery, particularly in the development of novel anti-inflammatory, anticancer, and antimicrobial agents. This research briefing provides an overview of the latest findings related to this compound, highlighting its synthesis, biological activity, and mechanistic insights.

One of the key areas of investigation has been the synthesis and optimization of 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid derivatives. A 2023 study published in the Journal of Medicinal Chemistry demonstrated an efficient synthetic route for this compound, utilizing a one-pot cyclization reaction that significantly improved yield and purity. The study also explored the structural-activity relationship (SAR) of various derivatives, identifying specific modifications that enhance binding affinity to target proteins such as COX-2 and HDACs.

In terms of biological activity, recent preclinical studies have revealed promising results. For instance, a 2024 paper in Bioorganic & Medicinal Chemistry Letters reported that 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid exhibits potent inhibitory effects against certain cancer cell lines, including breast and lung cancer, through the modulation of apoptosis-related pathways. Additionally, its anti-inflammatory properties were validated in a murine model of rheumatoid arthritis, where it significantly reduced pro-inflammatory cytokine levels.

Mechanistic studies have further elucidated the compound's mode of action. Advanced computational modeling and X-ray crystallography have provided insights into its binding interactions with key enzymatic targets. For example, a 2023 study in Nature Communications detailed how the oxadiazole ring of the compound forms critical hydrogen bonds with the active site of HDAC6, a target implicated in neurodegenerative diseases and cancer.

Despite these advancements, challenges remain in the clinical translation of 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid. Issues such as bioavailability, metabolic stability, and potential off-target effects need to be addressed through further research. Ongoing studies are focusing on prodrug strategies and nanoparticle-based delivery systems to overcome these limitations.

In conclusion, 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid (CAS: 95124-68-8) represents a promising candidate for therapeutic development, with recent research underscoring its potential in multiple disease areas. Continued exploration of its derivatives and mechanisms will be crucial for advancing its clinical applications.

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