133387-31-2

Upstream product

• 123-75-1 pyrrolidine 
• 611-06-3 2,4-dichloronitrobenzene 
• 120-94-5 1-Methylpyrrolidine 
• 2106-50-5 2-chloro-4-fluoro-1-nitrobenzene 

Relevant academic research and scientific papers

Substituted N-(4-amino-2-chlorophenyl)-5-chloro-2-hydroxybenzamide analogues potently inhibit respiratory syncytial virus (RSV) replication and RSV infection-associated inflammatory responses

Respiratory syncytial virus (RSV) is a leading cause of lower respiratory tract infection in young children, and specific treatment for RSV infections remains unavailable. We herein reported a series of substituted N-(4-amino-2-chlorophenyl)-5-chloro-2-hydroxybenzamide analogues as potent RSV inhibitors. Among them, six low cytotoxic compounds (11, 12, 15, 22, 26, and 28) have been identified and selected to study associated inhibitory mechanisms. All these compounds suppressed not only the viral replication but also RSV-induced IRF3 and NF-κB activation and associated production of cytokines/chemokines. The two most potent compounds (15 and 22) were selected for further molecular mechanism studies associated with their suppression effect on RSV-activated IRF3 and NF-κB. These two compounds decreased RSV-induced IRF3 phosphorylation at serine 396 and p65 phosphorylation at serine 536 at both early and late infection phases. In addition, compound 22 also inhibited RSV-induced p65 phosphorylation at serine 276 at the late phase of RSV infection.

Reaction of Mono-, Di-, and Trichloronitrobenzenes with N-Methyl Substituted Cyclic Tertiary Amines under High Pressure

The reactions of mono-, di-, and trichloronitrobenzenes with 1-methylpyrrolidine under high pressure gave products of demethylation and ring-opening through a quaternary pyrrolidinium chloride intermediate formed by the SNAr reaction.On the other hand, the reactions with 1-methylpiperidine and 4-methylmorpholine gave only demethylation products.The selectivities of the resctions of 1-methylpyrrolidine with these chloronitrobenzenes were found to be effected by the neighboring substituent to the pyrrolidinium group.

Nucleophilic Substitution Reaction of Aromatic Chlorides with Cyclic Tertiary Amines under High Pressure

The reaction of p-chloronitrobenzene with N-methylpyrrolidine under high pressure gave demethylation product and ring opening products through quaternary ammonium chloride intermediate formed by the SNAr reaction.On the other hand, the reactions with N-methylpiperidine and N-methylmorpholine gave only demethylation products.The reactions of o-chloronitrobenzene and 2,4-dichloronitrobenzene with above amines gave similar results.

Aromatic Nucleophilic Substitution of Halobenzenes with Amines under High Pressure

The nucleophilic substitution reactions of aromatic halides having electron-attracting groups on ortho or para position with various primary and secondary amines were accelerated by high pressure to give the corresponding N-substituted anilines in high yields.The bulkiness of amines affects its reactivity to lower the yields of the products.Although the secondary amines are usually less reactive than primary amines, cyclic secondary amines such as morpholine, piperidine, and pyrrolidine were found very reactive. 1,4-Diazabicyclooctane and quinuclidine gave N-quarternary ammonium halides in high yields in contrast to the low reactivity of acyclic tertiary amines.Dichloro- and trichloro-nitrobenzenes also react with diethylamine, pyrrolidine, and morpholine to give mono-, di-, and trisubstitution products depending upon the amount of amine and the position of nitro group in these chlorides.