50737-29-6

Usage

Uses

Used in Pharmaceutical Industry:
5-(Chloromethyl)-3-(4-methylphenyl)-1,2,4-oxadiazole is used as a building block for the synthesis of bioactive compounds due to its potential antimicrobial, anti-inflammatory, and antitumor properties. Its unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Agricultural Industry:
In the agricultural sector, 5-(Chloromethyl)-3-(4-methylphenyl)-1,2,4-oxadiazole is used as a precursor for the development of novel agrochemicals with enhanced pesticidal and herbicidal properties. Its ability to act as a building block for the synthesis of bioactive compounds makes it a valuable asset in the creation of more effective and environmentally friendly agricultural products.
However, it is important to note that further research is needed to fully understand the potential uses and effects of 5-(Chloromethyl)-3-(4-methylphenyl)-1,2,4-oxadiazole. Its diverse range of biological activities and potential applications in various industries make it a compound of interest in drug discovery and development, as well as in the agricultural sector.

InChI:InChI=1/C10H9ClN2O/c1-7-2-4-8(5-3-7)10-12-9(6-11)14-13-10/h2-5H,6H2,1H3

Upstream product

• 93335-40-1 (Z)-N'-(2-chloroacetoxy)-4-methylbenzimidamide 
• 19227-13-5 (Z)-N'-hydroxy-4-methylbenzimidamide 
• 79-04-9 chloroacetyl chloride 
• 19227-13-5 N'-hydroxy-4-methyl-benzamidine 
• 19227-13-5 p-toluamidoxime 
• 104-85-8 para-methylbenzonitrile 

Downstream Products

• 1119433-31-6 3-phenyl-5-{(3-p-tolyl-1,2,4-oxadiazol-5-yl)methylthio}-1,3,4-thiadiazole-2(3H)-thione 
• 865571-13-7 C₂₃H₁₇ClN₆OS 
• 1257542-54-3 C₂₄H₂₀N₆O₃ 
• 1257542-92-9 C₂₃H₁₇ClN₆OS 
• 1247705-79-8 5-(azidomethyl)-3-p-tolyl-1,2,4-oxadiazole 
• 708284-23-5 isopropyl-([3-(p-tolyl)-[1,2,4]oxadiazol-5-yl]methyl)amine 
• 890324-74-0 C-(3-p-tolyl-[1,2,4]oxadiazol-5-yl)methylamine 
• 708994-70-1 PI-1833 
• 890324-79-5 methyl-[(3-p-tolyl-[1,2,4]oxadiazol-5-yl)methyl]amine 
• 890324-84-2 ethyl-[(3-p-tolyl-[1,2,4]oxadiazol-5-yl)methyl]amine 
• 1274723-08-8 isobutyl-[(3-p-tolyl-[1,2,4]oxadiazol-5-yl)methyl]amine 
• 876893-45-7 tert-butyl-[(3-p-tolyl-[1,2,4]oxadiazol-5-yl)methyl]amine 
• 1178398-86-1 cyclopropyl-[(3-p-tolyl-[1,2,4]oxadiazol-5-yl)methyl]amine 
• 1401223-03-7 N-isopropyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(4-(trifluoromethyl)phenoxy)acetamide 

Relevant academic research and scientific papers

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, 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.

PROTEASOME CHYMOTRYPSIN-LIKE INHIBITION USING PI-1833 ANALOGS

Focused library synthesis and medicinal chemistry on an oxadiazole- isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring?s para-position and meta-pyridyl group at the B- ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer)

Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3] triazoles

1,2,4-Oxadiazole and 1,2,3-triazole containing heterocyclic compounds continue to gain interest in synthesis of chemical entities and exhibit various biological activities as anti-protozoal and anti-cancer agents. By using the principle of bioisosterism,

AZOLE DERIVATIVES AS WTN PATHWAY INHIBITORS

The present invention relates to new compounds of formula I, to processes for their preparation, to pharmaceutical formulations containing such compounds and to their use in therapy. Such compounds find particular use in the treatment and/or prevention of conditions or diseases which are affected by over-activation of signaling in the Wnt pathway. For example, these may be used in preventing and/or retarding proliferation of tumor cells, for example carcinomas such as colon carcinomas.