503859-26-5

Basic information

• Product Name: 3-Nitro-4-(Cyclohexylamino) Benzoic Acid Methyl Ester
• Synonyms: 3-Nitro-4-(Cyclohexylamino) Benzoic Acid Methyl Ester;Benzoic acid, 3-nitro-4-(cyclohexylamino)-,methyl ester;Methyl 4-(cyclohexylaMino)-3-nitrobenzoate
• CAS NO: 503859-26-5
• Molecular Formula: C₁₄H₁₈N₂O₄
• Molecular Weight: 278.30372
• Mol File: 503859-26-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 88 °C
• Boiling Point: 440.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.258±0.06 g/cm3(Predicted)
• PKA: -1.16±0.20(Predicted)
• CAS DataBase Reference: 3-Nitro-4-(Cyclohexylamino) Benzoic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitro-4-(Cyclohexylamino) Benzoic Acid Methyl Ester(503859-26-5)
• EPA Substance Registry System: 3-Nitro-4-(Cyclohexylamino) Benzoic Acid Methyl Ester(503859-26-5)

Safety Data

• Hazardous Substances Data: 503859-26-5(Hazardous Substances Data)

Upstream product

• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 108-91-8 cyclohexylamine 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 329-59-9 4-fluoro-3-nitro-benzoic acid methyl ester 

Downstream Products

• 503859-27-6 methyl 3-amino-4-(cyclohexylamino)benzoate 
• 1239608-90-2 methyl 6-oxo-8,8-dimethyl-11-cyclohexyl-5-(4-methoxyphenyl)-5,6,7,8,9,11-hexahydro-7H-4b,10,11-triazabenzo[b]fluorene-3-carboxylate 
• 1430101-87-3 C₂₀H₂₂N₄O₂ 
• 1430101-76-0 methyl 1-cyclohexyl-2-(3-(cyclohexylamino)-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-7-yl)-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-75-9 methyl 1-cyclohexyl-2-(3-(cyclohexylamino)-2-p-tolylimidazo[1,2-a]pyridin-7-yl)-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-74-8 methyl 2-(3-(benzylamino)-2-(furan-2-yl)imidazo[1,2-a]pyridin-7-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-73-7 methyl 2-(3-(benzylamino)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-72-6 methyl 2-(3-(benzylamino)-2-phenylimidazo[1,2-a]pyridin-7-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate 

Relevant articles and documents

Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization

Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds. An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray analysis and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney d-amino acid oxidase (pkDAO).

Novel Ferroptosis Inhibitors with Improved Potency and ADME Properties

Ferroptosis is a nonapoptotic, iron-catalyzed form of regulated necrosis that is critically dependent on glutathione peroxidase 4 (GPX4). It has been shown to contribute to liver and kidney ischemia reperfusion injury in mice. A chemical inhibitor discovered by high-throughput screening displayed inhibition of ferroptosis with nanomolar activity and was dubbed ferrostatin-1 (fer-1). Ferrostatins inhibit oxidative lipid damage, but suffer from inherent stability problems due to the presence of an ester moiety. This limits the application of these molecules in vivo, due to rapid hydrolysis of the ester into the inactive carboxylic acid. Previous studies highlighted the importance of the ethyl ester and suggested steric modifications of the ester for generating improved molecules. In this study, we report the synthesis of novel ferroptosis inhibitors containing amide and sulfonamide moieties with improved stability, single digit nanomolar antiferroptotic activity, and good ADME properties suitable for application in in vivo disease models.

COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS

The present invention provides, inter alia, a compound having the structure: (Formula (I). Also provided are compositions containing a pharmaceutically acceptable carrier and a compound according to the present invention. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, and methods for treating or ameliorating the effects of a neurodegenerative disease.