57238-75-2

Usage

Uses

Used in Pharmaceutical Industry:
5-(CHLOROMETHYL)-3-(4-CHLOROPHENYL)-1,2,4-OXADIAZOLE is used as a building block for the synthesis of new drugs due to its unique reactivity and structural properties, which facilitate the creation of biologically active compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(CHLOROMETHYL)-3-(4-CHLOROPHENYL)-1,2,4-OXADIAZOLE is utilized as a component in the development of new agrochemicals, leveraging its chemical properties to enhance the effectiveness of these products.
Used in Antimicrobial Applications:
5-(CHLOROMETHYL)-3-(4-CHLOROPHENYL)-1,2,4-OXADIAZOLE is used as an antimicrobial agent for its potential to combat various microorganisms, contributing to the field of infectious disease treatment and prevention.
Used in Anticancer Applications:
5-(CHLOROMETHYL)-3-(4-CHLOROPHENYL)-1,2,4-OXADIAZOLE is also used as an anticancer agent, showing promise in preliminary studies for its ability to target and potentially treat cancer cells, offering a new avenue for cancer therapy development.

InChI:InChI=1/C9H6Cl2N2O/c10-5-8-12-9(13-14-8)6-1-3-7(11)4-2-6/h1-4H,5H2

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 613-92-3 N-hydroxyl-benzamidine 
• 93048-83-0 (Z)-N'-(2-chloroacetoxy)-4-chlorobenzimidamide 
• 79-04-9 chloroacetyl chloride 
• 5033-28-3 4-chloro-N'-hydroxybenzimidamide 
• 623-03-0 4-Cyanochlorobenzene 
• 100-47-0 benzonitrile 
• 5033-28-3 4-chlorobenzamidoxime 
• 5033-28-3 4-chloro-N-hydroxybenzimidamide 
• 93048-83-0 4-chloro-N-chloroacetoxy-benzamidine 

Downstream Products

• 93405-18-6 3-(4-chlorophenyl)-5-(pyrrolidin-1-ylmethyl)-1,2,4-oxadiazole 
• 73217-39-7 1-[3-(4-chloro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-pyridinium; chloride 
• 5372-40-7 3-(4-chlorophenyl)-5-(hydroxymethyl)-1,2,4-oxadiazole 
• 531506-44-2 7-[(2-trimethylsilyl)ethoxymethyl]-8-[4-{[3-(4-chlorophenyl)(1,2,4-oxadiazol-5-yl)]methoxy}phenyl]-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione 
• 73217-50-2 N'-[3-(4-chloro-phenyl)-[1,2,4]oxadiazol-5-ylmethylene]-N,N-dimethyl-benzene-1,4-diamine N'-oxide 
• 1138333-15-9 3-{3-[3-(4-Chloro-phenyl)-[1,2,4]oxadiazol-5-ylmethoxy]-2,6-difluorophenyl}-4H-[1,2,4]oxadiazol-5-one 
• 865666-96-2 C₂₃H₁₇ClN₆O₂S 
• 1257542-58-7 C₂₄H₂₁N₇O₂ 
• 708252-66-8 {[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl}(isopropyl)amine 
• 1401223-06-0 N-((3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)methyl)-N-isopropyl-2-(4-(trifluoromethyl)phenoxy)acetamide 
• 757201-10-8 2-(4-chlorophenoxy)-N-((3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)methyl)-N-isopropylacetamide 
• 892011-58-4 N-((3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)methyl)-N-isopropyl-2-(p-tolyloxy)acetamide 

Relevant academic research and scientific papers

CARBOXY DERIVATIVES WITH ANTIINFLAMMATORY PROPERTIES

The invention relates to compounds of formula (I) and to their use in treating or preventing an inflammatory disease or a disease associated with an undesirable immune response: (I) wherein, RA1, RA2, RC and RD are as defined herein.

One-potCuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4/1,2,4-oxadiazoles starting from available chloromethyl-1,3,4/1,2,4-oxadiazoles

The one-pot CuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4-oxadiazole and (1H-1,2,3-triazol-1-yl)methyl-1,2,4-oxadiazole derivatives via three-component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “cli

Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties

Abstract: A tetraazacrown ether,4,9-di(prop-2-yn-1-yl)-1,4,9,12-tetraazacyclohexadecane-2,11-dione, bearingpropargyl groups on two nitrogens was synthesized starting from1,4,9,12-tetraazacyclohexadecane-2,11-dione and subjected to 1,3-cycloadditionreactio

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpro

Design, synthesis, and bioactivities of novel oxadiazole-substituted pyrazole oximes

A series of novel pyrazole oxime derivatives containing a substituted oxadiazole group were designed and synthesized. The bioassay results indicated that some title compounds displayed good acaricidal and insecticidal activities against Tetranychus cinnabarinus, Aphis medicaginis, Oriental armyworm, and Nilaparvata lugens. Especially, compounds 7a, 7b, and 7c had 80%, 90%, and 90% insecticidal activities against A. medicaginis at 20 μg/mL, respectively. Interestingly, some of the designed compounds displayed wonderful fungicidal activities in vivo against cucumber Pseudoperonospora cubensis. Furthermore, compounds 7a (EC50= 4.97 μg/mL) and 7h (EC50= 0.51 μg/mL) showed excellent fungicidal activity against P. cubensis comparable or better than that of the control Pyraclostrobin (EC50= 4.59 μg/mL).

Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents

A number of acridone-based oxadiazoles 11a–n have been synthesized and evaluated for their anticonvulsant activity against pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. Also, their neurotoxicity was evaluated by the rotarod test. Most of the compounds exhibited better anticonvulsant activity and higher safety respect to the standard drug, phenobarbital. Among the tested derivatives, compounds 11l with ED50value of 2.08?mg/kg was the most potent compound in the PTZ test. The anticonvulsant effect of compound 11l was blocked by flumazenil, suggesting the involvement of benzodiazepine (BZD) receptors in the anticonvulsant activity of prototype compound 11l. Also, docking study of compound 11l in the BZD-binding site of GABAAreceptor confirms possible binding of compound 11l with BZD receptors.

Discovery and preliminary evaluation of 2-aminobenzamide and hydroxamate derivatives containing 1,2,4-oxadiazole moiety as potent histone deacetylase inhibitors

Using Entinostat as a lead compound, 2-aminobenzamide and hydroxamate derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro antiproliferative activities using the MTT-based assay against five human cancer cell lines including U937, A549, NCI-H661, MDA-MB-231 and HCT116. 2-Aminobenzamide series of compounds (10a-10j) demonstrated the most significant inhibition against human acute monocytic myeloid leukemia cell line U937, but no or poor activities against two human lung cancer cell lines. Furthermore, the target compounds were screened for their inhibitory activities against HDAC 1, 2, and 8. 2-Aminobenzamide derivatives (10) manifested a higher selectivity for HDAC 1 over HDAC 2, but were not active against HDAC 8. In contrast, most hydroxamate derivatives (11) inhibit HDAC 8 with lower IC50 values than SAHA and Entinostat. Docking study with selected compounds 10f and 11a revealed that the compounds might bind tightly to the binding pockets in HDAC 2 and HDAC 8, respectively. The results suggest that they may be promising lead compounds for the development of novel anti-tumor drug potentially via inhibiting HDACs.

Design, synthesis, biological evaluation, and docking study of acetylcholinesterase inhibitors: New acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids

In this study, novel acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids were designed, synthesized, and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activity. Among various synthesized compounds, 10-((1-((3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H)-one 10b showed the most potent anti-acetylcholinesterase activity (IC50 = 11.55 μm) being as potent as rivastigmine. Also docking outcomes were in good agreement with in vitro results confirming the dual binding inhibitory activity of compound 10b. A novel series of acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids were synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities.

Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsulfonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (1H, 13C, 2D), mass spectra, and physical characteristics (mp and Rfvalues). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors

Screening of the 50 000 ChemBridge compound library led to the identification of the oxadiazole-isopropylamide 1 (PI-1833) which inhibited chymotrypsin-like (CT-L) activity (IC50 = 0.60 μM) with little effects on the other two major proteasome proteolytic activities, trypsin-like (T-L) and postglutamyl-peptide-hydrolysis-like (PGPH-L). LC-MS/MS and dialysis show that 1 is a noncovalent and rapidly reversible CT-L inhibitor. Focused library synthesis provided 11ad (PI-1840) with CT-L activity (IC50 = 27 nM). Detailed SAR studies indicate that the amide moiety and the two phenyl rings are sensitive toward modifications. Hydrophobic residues, such as propyl or butyl in the para position (not ortho or meta) of the A-ring and a m-pyridyl group as B-ring, significantly improve activity. Compound 11ad (IC50 = 0.37 μM) is more potent than 1 (IC50 = 3.5 μM) at inhibiting CT-L activity in intact MDA-MB-468 human breast cancer cells and inhibiting their survival. The activity of 11ad warrants further preclinical investigation of this class as noncovalent proteasome inhibitors.