1449372-46-6

Basic information

• Product Name: N-(4-amino-3-nitrophenyl)-N-[(4-fluorophenyl)methyl](phenylmethoxy)carboxamide
• Synonyms: N-(4-amino-3-nitrophenyl)-N-[(4-fluorophenyl)methyl](phenylmethoxy)carboxamide
• CAS NO: 1449372-46-6
• Molecular Weight: 395.39
• Mol File: 1449372-46-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4-amino-3-nitrophenyl)-N-[(4-fluorophenyl)methyl](phenylmethoxy)carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-amino-3-nitrophenyl)-N-[(4-fluorophenyl)methyl](phenylmethoxy)carboxamide(1449372-46-6)
• EPA Substance Registry System: N-(4-amino-3-nitrophenyl)-N-[(4-fluorophenyl)methyl](phenylmethoxy)carboxamide(1449372-46-6)

Safety Data

• Hazardous Substances Data: 1449372-46-6(Hazardous Substances Data)

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 150812-22-9 2-amino-5-(4-fluorobenzylideneamino)nitrobenzene 
• 5307-14-2 2-nitro-1,4-phenylenediamine 

Downstream Products

• 150812-12-7 Retigabine 
• 1449372-53-5 benzyl (4-((ethoxycarbonyl)amino)-3-nitrophenyl)(4-fluorobenzyl)carbamate 

Relevant articles and documents

Discovery of Aromatic Carbamates that Confer Neuroprotective Activity by Enhancing Autophagy and Inducing the Anti-Apoptotic Protein B-Cell Lymphoma 2 (Bcl-2)

Neurodegenerative diseases share certain pathophysiological hallmarks that represent common targets for drug discovery. In particular, dysfunction of proteostasis and the resultant apoptotic death of neurons represent common pathways for pharmacological intervention. A library of aromatic carbamate derivatives based on the clinically available drug flupirtine was synthesized to determine a structure-activity relationship for neuroprotective activity. Several derivatives were identified that possess greater protective effect in human induced pluripotent stem cell-derived neurons, protecting up to 80% of neurons against etoposide-induced apoptosis at concentrations as low as 100 nM. The developed aromatic carbamates possess physicochemical properties desirable for CNS therapeutics. The primary known mechanisms of action of the parent scaffold are not responsible for the observed neuroprotective activity. Herein, we demonstrate that neuroprotective aromatic carbamates function to increase the Bcl-2/Bax ratio to an antiapoptotic state and activate autophagy through induction of beclin 1.

Synthesis and evaluation of potent KCNQ2/3-specific channel activators

KQT-like subfamily (KCNQ) channels are voltage-gated, non-inactivating potassium ion channels, and their down-regulation has been implicated in several hyperexcitability-related disorders, including epilepsy, neuropathic pain, and tinnitus. Activators of these channels reduce the excitability of central and peripheral neurons, and, as such, have therapeutic utility. Here, we synthetically modified several moieties of the KCNQ2-5 channel activator retigabine, an anticonvulsant approved by the U.S. Food and Drug Administration. By introducing a CF3-group at the 4-position of the benzylamine moiety, combined with a fluorine atom at the 3-position of the aniline ring, we generated Ethyl (2-amino-3-fluoro-4-((4-(trifluoromethyl)benzyl)amino)phenyl)carbamate (RL648-81), a new KCNQ2/3-specific activator that is >15 times more potent and also more selective than retigabine. We suggest that RL648-81 is a promising clinical candidate for treating or preventing neurologic disorders associated with neuronal hyperexcitability.