180207-82-3

Basic information

• Product Name: Isopropyl-(2-Methyl-6-nitro-phenyl)-aMine
• Synonyms: Isopropyl-(2-Methyl-6-nitro-phenyl)-aMine;N-Isopropyl-2-Methyl-6-nitroaniline
• CAS NO: 180207-82-3
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23036
• Mol File: 180207-82-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isopropyl-(2-Methyl-6-nitro-phenyl)-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl-(2-Methyl-6-nitro-phenyl)-aMine(180207-82-3)
• EPA Substance Registry System: Isopropyl-(2-Methyl-6-nitro-phenyl)-aMine(180207-82-3)

Safety Data

• Hazardous Substances Data: 180207-82-3(Hazardous Substances Data)

Upstream product

• 41085-43-2 2-bromo-3-nitrotoluene 
• 75-31-0 isopropylamine 
• 570-24-1 2-Methyl-6-nitroaniline 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 240143-40-2 1-isopropyl-7-methyl-1,3-dihydro-benzoimidazol-2-one 
• 180207-83-4 1-isopropyl-6-methyl-1,2-phenylenediamine 

Relevant articles and documents

2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamides with selective affinity for the 5-HT4 receptor: Synthesis and structure-affinity and structure-activity relationships of a new series of partial agonist and antagonist derivatives

A series of 2,3-dihydro-2-oxo-1H-benzimidazole-l-carboxamide derivatives bearing a piperazine moiety was synthesized. Their in vitro 5-HT4, 5-HT3, and D2 receptors affinities were evaluated by radioligand binding assay. For selected compounds functional studies at the 5-HT4 receptor were made by using precontracted (by carbachol) preparations of rat esophageal tunica muscularis mucosae (TMM). The influence of the 3-substituent of the benzimidazole ring, the 4-substituent of the piperazine moiety, and the alkylene spacer was studied. Compounds with an ethyl or a cyclopropyl substituent in the 3-position of the benzimidazole ring showed moderate to high affinity (K(i) = 6.7-75.4 nM) for the 5-HT4 receptor with selectivity over 5-HT3 and D2 receptors and moderate antagonist activity (pK(b) = 6.19- 7.73). Compounds with an isopropyl substituent in the 3-benzimidazole position exhibited moderate and selective 5-HT4 affinity (K(i) ≥ 38.9 nM) and a partial agonist activity (5a, i.a. = 0.94) higher than that of the reference compound BIMU 8 (i.a. = 0.70). This reversal of the pharmacological activity due only to a small structural difference might confirm the existence of two binding sites on the 5-HT4 receptor. In the alkylene spacer, a two-methylene chain is favorable to optimize the affinity and the antagonist or the partial agonist activity. In the ethyl and cyclopropyl series, 5-HT4 antagonist activity seems to be unrelated to the size of the 4-substituent of the piperazine moiety, whereas a methyl group is optimal for high partial agonist activity in the isopropyl series; however, the presence of a butyl substituent is a favorable pattern for 5-HT4 antagonism and even causes a reversal of the pharmacological profile in the isopropyl series (5h, pK(b) = 7.94). N-Butyl quaternization of 5a led to an improvement in affinity for the 5-HT4 receptor and maintained the high partial agonist activity (5r, K(i) = 66.3 nM, i.a. = 0.93).

3-Phenyl-substituted imidazo[1,5-a]quinoxalin-4-ones and imidazo[1,5- a]quinoxaline ureas that have high affinity at the GABA(A)/benzodiazepine receptor complex

A series of imidazo[1,5-a]quinoxalin-4-ones and imidazo[1,5- a]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo-[1,5-a]quinoxaline urea series had high affinity for the GABA(A)/benzodiaze