93335-40-1

Basic information

• Product Name: Benzenecarboximidamide, N-[(chloroacetyl)oxy]-4-methyl-
• CAS NO: 93335-40-1
• Molecular Formula: C10H11ClN2O2
• Molecular Weight: 226.663
• Mol File: 93335-40-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenecarboximidamide, N-[(chloroacetyl)oxy]-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenecarboximidamide, N-[(chloroacetyl)oxy]-4-methyl-(93335-40-1)
• EPA Substance Registry System: Benzenecarboximidamide, N-[(chloroacetyl)oxy]-4-methyl-(93335-40-1)

Safety Data

• Hazardous Substances Data: 93335-40-1(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 111457-42-2 3-p-Tolyl-4H-[1,2,4]oxadiazin-5-one 
• 50737-29-6 3-(4-methylphenyl)-5-(chloromethyl)-1,2,4-oxadiazole 
• 1401223-38-8 N-cyclopropyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(p-tolyloxy)acetamide 
• 1401223-37-7 N-tert-butyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(p-tolyloxy)acetamide 
• 891031-77-9 N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(p-tolyloxy)acetamide 
• 916029-86-2 N-methyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(p-tolyloxy)acetamide 
• 1004392-23-7 N-ethyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(p-tolyloxy)acetamide 
• 1401223-36-6 N-isobutyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(p-tolyloxy)acetamide 
• 1401223-34-4 N-isopropyl-2-(4-propylphenoxy)-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 892009-19-7 N-isopropyl-2-phenoxy-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 727363-91-9 2-(4-chlorophenoxy)-N-isopropyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-03-7 N-isopropyl-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)-2-(4-(trifluoromethyl)phenoxy)acetamide 
• 1178398-86-1 cyclopropyl-[(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 

Relevant articles and documents

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.

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).

REACTION OF AMIDOXIMES WITH α-CHLOROACID CHLORIDES: NOVEL SYNTHESIS OF 1,2,4-OXADIAZIN-5-ONES

The reaction of amidoximes with α-chloroacid chlorides gives under thermal reaction conditions 5-(1-chloroalkyl)-1,2,4-oxadiazoles.In presence of a strong base, the reaction follows a different path leading to the formation of 4H-1,2,4-oxadiazin-5(6H)-one