53919-74-7

Usage

Chemical Structure

1,2,4-Oxadiazole ring with a 2-chloroethyl group and a phenyl group

Usage

Commonly used in the synthesis of pharmaceuticals, agrochemicals, and dye stuffs

Biological Activities

Potential antifungal and antimicrobial activities

Derivatives

Shown anti-inflammatory, anticancer, and antiviral properties

Safety

Important to handle with caution and follow proper safety protocols due to potential toxicity and harmful effects if not used correctly

Upstream product

• 10560-64-2 N-[(3-chloropropanoyl)oxy]benzenecarboximidamide 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 20495-99-2 3-chloropropionic anhydride 
• 625-36-5 2-chloropropionyl chloride 
• 100-47-0 benzonitrile 
• 613-92-3 N-hydroxybenzamidine 
• 10560-64-2 N-[(chloropropionyl)oxy]benzenecarboximidamide 
• 613-92-3 N-hydroxyl-benzamidine 
• 10560-64-2 (Z)-N’-(2-chloropropanoyloxy)benzimidamide 
• 542-76-7 3-Chloropropionitrile 

Downstream Products

• 92440-21-6 4-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]morpholine 
• 94090-96-7 1-methyl-4-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]piperazine 
• 959-14-8 oxolamine 
• 1043537-84-3 isopropyl-[2-(3-phenyl-[1,2,4]oxadiazol-5-yl)ethyl]amine 
• 21891-79-2 N,N-dimethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine 
• 92439-99-1 3-phenyl-5-[2-(pyrrolidin-1-yl)ethyl]-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Sigma-1 (σ1) Receptor Ligands Based on Phenyl-1,2,4-oxadiazole Derivatives

In this study, a series of phenyl-1,2,4-oxadiazole derivatives were synthesized and evaluated for anti-allodynic activity. Structure–activity relationship studies identified 1-{4-[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl]butyl}piperidine (39) with excellent affinity for the σ1 receptor and selectivity for the σ2 receptor, with poor activity to other central nervous system neurotransmitter receptors and transporters associated with pain. Compound 39 exhibited dose-dependent efficacy in suppressing the formalin-induced flinching and attenuating mechanical allodynia in chronic constriction injury-induced neuropathic rats. These results suggest that compound 39 exerts potent antihyperalgesic activity and could be considered as a promising candidate for treating neuropathic pain.

Nitrogenous heterocyclic compound with nematocidal activity, preparation method and application thereof

The invention relates to a nitrogenous heterocyclic compound with nematocidal activity, a preparation method and application thereof. Specifically, the invention discloses a compound with a formula (I) or an optical isomer, cis-trans isomer or acceptable salt in agricultural pharmacology and a preparation method thereof. The invention further discloses an agricultural composition containing the compound and application thereof. The compound has excellent nematocidal activity.

Discovery of novel heteroarylmethylcarbamodithioates as potent anticancer agents: Synthesis, structure-activity relationship analysis and biological evaluation

A series of new analogs based on the structure of lead compound 10 were designed, synthesized and evaluated for their in vitro anti-cancer activities against four selected human cancer cell lines (HL-60, Bel-7402, SK-BR-3 and MDA-MB-468). Several synthesized compounds exhibited improved anti-cancer activities comparing with lead compound 10. Among them, 1,3,4-oxadiazole analogs 17o showed highest bioactivity with IC50 values of 1.23, 0.58 and 4.29 μM against Bel-7402, SK-BR-3 and MDA-MB-468 cells, respectively. It is noteworthy that 17o has potent anti-proliferation activity toward a panel of cancer cells with relatively less cytotoxicity to nonmalignant cells. The further mechanistic study showed that it induced apoptosis and cell cycle arrest through disrupting spindle assembly in mitotic progression, indicating these synthesized dithiocarbamates represented a novel series of anti-cancer compounds targeting mitosis.

Pyridine methylamino dithio formic acid heteroaryl naphthenic base ester compound and preparation method and application thereof

The invention relates to a compound as shown in a general formula (I) or pharmaceutically acceptable salts or solvates thereof, and relates to a preparation method of the compound and application thereof in preparing anti-tumor drugs. Please see the general formula (I) in the description.

Efficient and convenient protocol for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using HClO4-SiO2 as a heterogeneous recyclable catalyst

Silica-supported perchloric acid (HClO4SiO2) was found to be a new, highly efficient, inexpensive, and reusable catalyst for a rapid and efficient synthesis of various 1,2,4-oxadiazoles with good to excellent yields under solvent-free conditions. The present methodology has been effectively utilized for the synthesis of oxolamine, an anti-inflammatory drug.

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)