54029-53-7

Basic information

• Product Name: Benzenamine, 2-nitro-4-[(phenylmethyl)thio]-
• CAS NO: 54029-53-7
• Molecular Formula: C13H12N2O2S
• Molecular Weight: 260.316
• Mol File: 54029-53-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenamine, 2-nitro-4-[(phenylmethyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2-nitro-4-[(phenylmethyl)thio]-(54029-53-7)
• EPA Substance Registry System: Benzenamine, 2-nitro-4-[(phenylmethyl)thio]-(54029-53-7)

Safety Data

• Hazardous Substances Data: 54029-53-7(Hazardous Substances Data)

Upstream product

• 54029-45-7 2-nitro-4-thiocyanoaniline 
• 100-39-0 benzyl bromide 
• 80983-47-7 4-amino-3-nitrobenzenethiol 
• 875-51-4 4-Bromo-2-nitroaniline 
• 100-53-8 phenylmethanethiol 
• 55791-06-5 benzyl mesylate 

Downstream Products

• 99314-90-6 5⁽⁶⁾-benzylsulphonobenzimidazole 
• 99314-89-3 5-Benzylsulfanyl-2-methyl-1H-benzoimidazole 
• 99314-88-2 5⁽⁶⁾-benzylthiobenzimidazole 
• 54029-70-8 4-benzylmercapto-o-phenylenediamine 

Relevant articles and documents

Sulfonamides as Selective NaV1.7 Inhibitors: Optimizing Potency, Pharmacokinetics, and Metabolic Properties to Obtain Atropisomeric Quinolinone (AM-0466) that Affords Robust in Vivo Activity

Because of its strong genetic validation, NaV1.7 has attracted significant interest as a target for the treatment of pain. We have previously reported on a number of structurally distinct bicyclic heteroarylsulfonamides as NaV1.7 inhibitors that demonstrate high levels of selectivity over other NaV isoforms. Herein, we report the discovery and optimization of a series of atropisomeric quinolinone sulfonamide inhibitors [ Bicyclic sulfonamide compounds as sodium channel inhibitors and their preparation. WO 2014201206, 2014 ] of NaV1.7, which demonstrate nanomolar inhibition of NaV1.7 and exhibit high levels of selectivity over other sodium channel isoforms. After optimization of metabolic and pharmacokinetic properties, including PXR activation, CYP2C9 inhibition, and CYP3A4 TDI, several compounds were advanced into in vivo target engagement and efficacy models. When tested in mice, compound 39 (AM-0466) demonstrated robust pharmacodynamic activity in a NaV1.7-dependent model of histamine-induced pruritus (itch) and additionally in a capsaicin-induced nociception model of pain without any confounding effect in open-field activity.

Bicyclic sulfonamide compounds as sodium channel inhibitors

The present invention provides compounds of Formula I, and pharmaceutically acceptable salts thereof, that are inhibitors of voltage-gated sodium channels, in particular Nav1.7. The compounds are useful for the treatment of diseases associated with the activity of sodium channels such as pain disorders and itch. Also provided are pharmaceutical compositions containing compounds of the present invention.

Certain thiazolidine and tetrahydrothiazine compounds

Benzene derivatives of the formula: STR1 wherein R1 is alkyl, R2 is a group --SR3, --SOR3, --SO2 R3 or --OR3, in which R3 is alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl or cycloalkylalkyl, whose position on the benzene ring is either para to --NHCOAZ or para to the heterocyclo group, A is a C1-4 aliphatic hydrocarbon radical, B is a bivalent methylene or ethylene group, and Z is a primary, secondary or tertiary amino group, and acid addition salts and quaternary ammonium derivatives thereof, are new compounds useful as anthelmintics and antifungal agents.