92109-03-0

Basic information

• Product Name: 3-NITRO-4-(HEXAMETHYLENEIMIN-1-YL)BENZOIC ACID
• Synonyms: 1-(4-Carboxy-2-nitrophenyl)azepane, 1-(4-Carboxy-2-nitrophenyl)homopiperidine
• CAS NO: 92109-03-0
• Molecular Formula: C₁₃H₁₆N₂O₄
• Molecular Weight: 264.28
• Mol File: 92109-03-0.mol

Chemical Properties

• Boiling Point: 462°Cat760mmHg
• Flash Point: 233.2°C
• Appearance: /
• Density: 1.296g/cm³
• Vapor Pressure: 2.47E-09mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 3-NITRO-4-(HEXAMETHYLENEIMIN-1-YL)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITRO-4-(HEXAMETHYLENEIMIN-1-YL)BENZOIC ACID(92109-03-0)
• EPA Substance Registry System: 3-NITRO-4-(HEXAMETHYLENEIMIN-1-YL)BENZOIC ACID(92109-03-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 92109-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Nitro-4-(hexamethyleneimin-1-yl)benzoic acid is used as a precursor in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry Reactions:
As a reagent in organic chemistry, 3-Nitro-4-(hexamethyleneimin-1-yl)benzoic acid facilitates various chemical reactions, enabling the synthesis of complex organic molecules for research and industrial purposes.
Used in Polymer Production:
3-Nitro-4-(hexamethyleneimin-1-yl)benzoic acid is utilized in the production of polymers, where its properties can influence the polymer's characteristics, such as stability, solubility, and reactivity.
Used in Material Development:
3-NITRO-4-(HEXAMETHYLENEIMIN-1-YL)BENZOIC ACID serves as a component in the development of new materials, where its unique structure and properties can contribute to the creation of innovative materials with specific functionalities.

InChI:InChI=1/C13H16N2O4/c16-13(17)10-5-6-11(12(9-10)15(18)19)14-7-3-1-2-4-8-14/h5-6,9H,1-4,7-8H2,(H,16,17)

Upstream product

• 71302-98-2 ethyl 4-(azepan-1-yl)-3-nitrobenzoate 
• 111-49-9 hexamethylene imine 
• 453-71-4 3-nitro-4-fluorobenzoic acid 

Relevant articles and documents

Mechanisms of action of novel influenza A/M2 viroporin inhibitors derived from hexamethylene amiloride

The increasing prevalence of influenza viruses with resistance to approved antivirals highlights the need for new anti-influenza therapeutics. Here we describe the functional properties of hexamethylene amiloride (HMA)'derived compounds that inhibit the wildtype and adamantane-resistant forms of the influenza A M2 ion channel. For example, 6-(azepan-1-yl)-N-carbamimidoylnicotinamide (9) inhibits amantadine-sensitive M2 currents with 3- to 6-fold greater potency than amantadine or HMA (IC50 5 0.2 vs. 0.6 and 1.3 μM, respectively). Compound 9 competes with amantadine for M2 inhibition, and molecular docking simulations suggest that 9 binds at site(s) that overlap with amantadine binding. In addition, tert-butyl 4′-(carbamimidoylcarbamoyl)-2′,3-dinitro- [1,1′-biphenyl]-4-carboxylate (27) acts both on adamantanesensitive and a resistantM2variant encoding a serine to asparagine 31 mutation (S31N) with improved efficacy over amantadine and HMA (IC5050.6 μMand4.4mM, respectively).Whereas 9 inhibited in vitro replication of influenza virus encoding wild-type M2 (EC505 2.3 μM), both 27 and tert-butyl 4′-(carbamimidoylcarbamoyl)-2′,3- dinitro-[1,1′-biphenyl]-4-carboxylate (26) preferentially inhibited viruses encoding M2(S31N) (respective EC50 5 18.0 and 1.5 μM). This finding indicates thatHMAderivatives can be designed to inhibit viruses with resistance to amantadine. Our study highlights the potential of HMA derivatives as inhibitors of drug-resistant influenza M2 ion channels.

OXADIAZOLE DIARYL COMPOUNDS

The invention relates to compounds of formula (I): wherein R1, R2, Ra , Rb,Rc and W, have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.