1201-68-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole serves as a valuable building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and functional groups make it a key component in the development of new drugs and pesticides, enhancing their efficacy and selectivity.
Used in Fluorescence Sensing Applications:
3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole has demonstrated potential as a fluorescence sensor for the detection of metal ions. Its ability to selectively bind and respond to specific metal ions makes it a promising candidate for environmental monitoring, medical diagnostics, and other analytical applications.
Used in Antimicrobial and Antifungal Research:
3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole has exhibited antimicrobial and antifungal activities, making it a valuable compound for research and development in the fields of medicine and agriculture. Its broad-spectrum activity against various pathogens highlights its potential as a novel therapeutic agent or as a component in antimicrobial formulations.
Used in the Chemical Industry:
3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole is used as a key intermediate in the synthesis of various organic compounds. Its reactivity and functional groups make it a versatile building block for the preparation of a wide range of chemical products, including dyes, polymers, and other specialty chemicals.

InChI:InChI=1/C9H7ClN2O/c10-6-8-11-9(13-12-8)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 3272-96-6 (Z)-2-chloro-N'-hydroxyethanimidamide 
• 98-88-4 benzoyl chloride 
• 3272-96-6 2-chloro-N-hydroxyethanimidamide 
• 1403889-97-3 (E)-2-chloro-N'-hydroxy ethenimidamide 
• 3272-96-6 2-chloro-N'-hydroxyacetimidamide 
• 255876-57-4 C₉H₉ClN₂O₂ 

Downstream Products

• 73217-28-4 1-(5-phenyl-[1,2,4]oxadiazol-3-ylmethyl)-pyridinium; chloride 
• 73217-37-5 (5-phenyl-[1,2,4]oxadiazol-3-yl)-methanol 
• 1026239-20-2 1-[3-(5-phenyl-[1,2,4]oxadiazol-3-ylmethoxy)-phenyl]-ethanone 
• 174180-70-2 2-[2,4-Dioxo-5-phenyl-3-(5-phenyl-[1,2,4]oxadiazol-3-ylmethyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenyl acetamide 
• 1073475-52-1 C₂₉H₂₆N₆O₂ 
• 1195981-95-3 (R)-3-(9-hydroxy-9H-xanthene-9-carbonyloxy)-1-(5-phenyl[1,2,4]oxadiazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 96127-40-1 diethyl (5-phenyl-1,2,4-oxadiazol-3-yl)methylphosphonate 
• 1273329-62-6 diethyl 1-(5-phenyl-1,2,4-oxadiazol-3-yl)ethylphosphonate 
• 1352565-21-9 (3R)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-(2-phenyl-2-(o-tolylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride 
• 1352565-20-8 (R)-3-(2-(3-(methylcarbamoyl)phenylamino)-2-phenylacetoxy)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1352565-19-5 (R)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride 
• 1352565-27-5 (3R)-1-methyl-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-(2-phenyl-2-(phenylamino)acetoxy)pyrrolidinium 2,2,2-trifluoroacetate 
• 1352565-23-1 (3R)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-(2-(phenylamino)-2-(thiophen-2-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate 
• 1352565-25-3 (3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate 

Relevant academic research and scientific papers

Novel N-Substituted oseltamivir derivatives as potent influenza neuraminidase inhibitors: Design, synthesis, biological evaluation, ADME prediction and molecular docking studies

The discovery of novel potent neuraminidase (NA) inhibitors remains an attractive approach for treating infectious diseases caused by influenza. In this study, we describe the design and synthesis of novel N-substituted oseltamivir derivatives for probing the 150-cavity which is nascent to the activity site of NA. NA inhibitory studies showed that new derivatives demonstrated the inhibitory activity with IC50 values at nM level against NA of a clinical influenza virus strain. Moreover, the in silico ADME predictions showed that the selected compounds had comparable properties with oseltamivir carboxylate, which demonstrated the druggablity of these derivatives. Furthermore, molecular docking studies showed that the most potent compound 6f and 10i could adopt different modes of binding interaction with NA, which may provide novel solutions for treating oseltamivir-resistant influenza. Based on the research results, we consider that compounds 6f and 10i have the potential for further studies as novel antiviral agents.

QUINUCLIDINE ESTERS OF 1-AZAHETEROCYCLYLACETIC ACID AS ANTIMUSCARINIC AGENTS, PROCESS FOR THEIR PREPARATION AND MEDICINAL COMPOSITIONS THEREOF

The invention relates to compounds of formula (I), wherein A, R1, R2, X, m and n are as defined in the specification, as selective M3 receptor antagonists, process for their preparation, composition comprising them and the therapeutic use thereof. Said co

QUINUCLIDINE ESTERS OF 1-AZAHETEROCYCLYLACETIC ACID AS ANTIMUSCARINIC AGENTS, PROCESS FOR THEIR PREPARATION AND MEDICINAL COMPOSITIONS THEREOF

Compounds of formula (I): wherein A, R1, R2, X, m, and n are as defined in the specification, are selective M3 receptor antagonists and may be used in the treatment of, inter alia, a respiratory disease such as asthma and COPD.

ALKALOID AMINOESTER DERIVATIVES AND MEDICINAL COMPOSITION THEREOF

The present invention relates to alkaloid aminoester compounds which act as muscarinic receptor antagonists, processes for the preparation of such a compound, compositions which contain such a compound, and therapeutic uses of such a compound.

ALKALOID AMINOESTER DERIVATIVES AND MEDICINAL COMPOSITION THEREOF

The present invention relates to alkaloid aminoester derivatives acting as muscarinic receptor antagonists, processes for their preparation, compositions comprising them and therapeutic uses thereof.

New GABA-modulating 1,2,4-oxadiazole derivatives and their anticonvulsant activity

A series of 3- and 5-aryl-1,2,4-oxadiazole derivatives were prepared and tested for anticonvulsant activity in a variety of models. These 1,2,4-oxadiazoles exhibit considerable activity in both pentylenetetrazole (PTZ) and maximal electroshock seizure (MES) models. Compound 10 was protective in the PTZ model in rats with an oral ED50 of 25.5 mg/kg and in the MES model in rats with an oral ED50 of 14.6 mg/kg. Neurotoxicity (rotarod) was observed with an ED50 of 335 mg/kg. We found several oxadiazoles that acted as selective GABA potentiating compounds with no interaction to the benzodiazepine binding site.

Novel 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)-xanthine derivatives as high affinity and selective A2B adenosine receptor antagonists

A series of new 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)- xanthine derivatives as A2B-AdoR antagonists have been synthesized and evaluated for their binding affinities for the A2B, A 1, A2A, and A3-AdoRs. 8-(1-((3-phenyl-1,2,4- oxadiazol-5-yl)methyl)-1H-pyrazol-4-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione (4) displayed high affinity (Ki = 1 nM) and selectivity for the A2B-AdoR versus A1, A2A, and A 3-AdoRs (A1/A2B, A2A/A2B, and A3/A2B selectivity ratios of 370, 1100, and 480, respectively). The synthesis and SAR of this novel class of compounds are presented herein.

New azolidinediones as inhibitors of protein tyrosine phosphatase lb with antihyperglycemic properties

Insulin resistance in the liver and peripheral tissues together with a pancreatic cell defect are the common causes of type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibiton of PTPases may be an effective method in the treatment of type 2 diabetes. A series of azolidinediones has been prepared as protein tyrosine phosphatase 1B (PTP1B) inhibitors. Several compounds were Potent inhibitors against the recombinant rat and human PTP1B enzymes with submicromolar IC50 values. Elongated spacers between the azolidinedione moiety and the central aromatic portion of the molecule as well as hydrophobic groups at the vicinity of this aromatic region were very important to the inhibitory activity. Oxadiazolidinediones 87 and 88 and the corresponding acetic acid analogues 119 and 120 were the best h-PTP1B inhibitors with IC50 values in the range of 0.12-0.3 μM. Several compounds normalized plasma glucose and insulin levels in the ob/ob and db/db diabetic mouse models.