51802-78-9

Basic information

• Product Name: 5-(CHLOROMETHYL)-3-(3-CHLOROPHENYL)-1,2,4-OXADIAZOLE
• Synonyms: 5-(CHLOROMETHYL)-3-(3-CHLOROPHENYL)-1,2,4-OXADIAZOLE;5-Chloromethyl-3-(3-chloro-phenyl)-;1,2,4-Oxadiazole, 5-(chloromethyl)-3-(3-chlorophenyl)-
• CAS NO: 51802-78-9
• Molecular Formula: C₉H₆Cl₂N₂O
• Molecular Weight: 229.06
• Mol File: 51802-78-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 356.8°C at 760 mmHg
• Flash Point: 169.6°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 5.87E-05mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-(CHLOROMETHYL)-3-(3-CHLOROPHENYL)-1,2,4-OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(CHLOROMETHYL)-3-(3-CHLOROPHENYL)-1,2,4-OXADIAZOLE(51802-78-9)
• EPA Substance Registry System: 5-(CHLOROMETHYL)-3-(3-CHLOROPHENYL)-1,2,4-OXADIAZOLE(51802-78-9)

Safety Data

• Hazardous Substances Data: 51802-78-9(Hazardous Substances Data)

Usage

General Description

5-(Chloromethyl)-3-(3-chlorophenyl)-1,2,4-oxadiazole is a chemical compound with the molecular formula C9H6Cl2N2O. It is a member of the oxadiazole family, which are heterocyclic compounds with a five-membered ring containing oxygen and nitrogen atoms. This particular compound is characterized by the presence of a chloromethyl group and a 3-chlorophenyl group on the oxadiazole ring. It is commonly used in pharmaceutical research and is being investigated for its potential biological activities, including its potential as an antiviral, antimicrobial, and anticancer agent. Its chemical structure and properties make it a versatile compound for various applications in the field of medicinal chemistry and drug discovery.

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

Upstream product

• 22179-77-7 3-chloro-N-hydroxy-benzamidine 
• 93048-81-8 C₉H₈Cl₂N₂O₂ 
• 22179-77-7 (Z)-3-chloro-N’-hydroxybenzimidamide 
• 766-84-7 3-chloro-benzonitrile 
• 79-04-9 chloroacetyl chloride 
• 93048-81-8 C₉H₈Cl₂N₂O₂ 
• 93048-81-8 3-chloro-N-chloroacetoxy-benzamidine 
• 22179-77-7 3-chloro-N-hydroxybenzimidamide 

Downstream Products

• 1359486-87-5 C₁₇H₁₂ClN₃O₃ 
• 1396013-15-2 C₁₉H₁₆ClN₃O₃ 

Relevant articles and documents

N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators

A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties.

The discovery of a selective, high affinity A2B adenosine receptor antagonist for the potential treatment of asthma

Adenosine has been suggested to play a role in asthma, possibly via activation of A2B adenosine receptors on mast cells and other pulmonary cells. We describe our initial efforts to discover a xanthine based selective A2B AdoR antagonist that resulted in the discovery of CVT-5440, a high affinity A2B AdoR antagonist with good selectivity (A2B AdoR Ki = 50 nM, selectivity A1 > 200: A2A > 200: A3 > 167).

Antikinetoplastid activity of 3-aryl-5-thiocyanatomethyl-1,2,4-oxadiazoles

A series of 5-thiocyanatomethyl- and 5-alkyl-3-aryl-1,2,4-oxadiazoles were synthesized and evaluated for their activity against kinetoplastid parasites. Formation of the oxadiazole ring was accomplished through the reaction of benzamidoximes with acyl chlorides, while the thiocyanate group was inserted by reacting the appropriate 5-halomethyl oxadiazole with ammonium thiocyanate. The thiocyanate-containing compounds possessed low micromolar activity against Leishmania donovani and Trypanosoma brucei, while the 5-alkyl oxadiazoles were less active against these parasites. 3-(4-Chlorophenyl)-5-(thiocyanatomethyl)-1, 2,4-oxadiazole (compound 4b) displayed modest selectivity for L. donovani axenic amastigote-like parasites over J774 macrophages, PC3 prostate cancer cells, and Vero cells (6.4-fold, 3.8-fold, and 9.1-fold, respectively), while 3-(3,4-dichlorophenyl)-5-(thiocyanatomethyl)-1,2,4-oxadiazole (compound 4h) showed 30-fold selectivity against Vero cells but was not selective against PC3 cells. In a murine model of visceral leishmaniasis, compound 4b decreased liver parasitemia caused by L. donovani by 48% when given in five daily i.v. doses at 5mg/kg and by 61% when administered orally for 5days at 50mg/kg. These results indicate that aromatic thiocyanates hold promise for the treatment of leishmanial infections if the selectivity of these compounds can be improved.