93048-81-8

Basic information

• Product Name: Benzenecarboximidamide, 3-chloro-N-[(chloroacetyl)oxy]-
• CAS NO: 93048-81-8
• Molecular Formula: C9H8Cl2N2O2
• Molecular Weight: 247.081
• Mol File: 93048-81-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzenecarboximidamide, 3-chloro-N-[(chloroacetyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenecarboximidamide, 3-chloro-N-[(chloroacetyl)oxy]-(93048-81-8)
• EPA Substance Registry System: Benzenecarboximidamide, 3-chloro-N-[(chloroacetyl)oxy]-(93048-81-8)

Safety Data

• Hazardous Substances Data: 93048-81-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 1396013-15-2 C₁₉H₁₆ClN₃O₃ 
• 51802-78-9 3-(3-chlorophenyl)-5-(chloromethyl)-1,2,4-oxadiazole 
• 97256-11-6 [3-(3-chloro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-diethyl-amine 

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.

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.