85355-46-0

Upstream product

• 108-05-4 vinyl acetate 
• 119-08-4 4-methyl-2-nitrobenzenediazonium chloride 
• 624-91-9 methyl nitrite 
• 126759-35-1 4-methyl-2-nitro-1-vinylbenzene 
• 20357-22-6 2-nitro-4-methylbenzaldehyde 
• 89-62-3 4-methyl-2-nitroaniline 

Downstream Products

• 1313592-01-6 methyl 1-[4-(1-methoxy-1-oxopropan-2-yl)-3-nitrobenzyl]-2-oxocyclopentanecarboxylate 
• 1313592-04-9 sodium 2-{2-nitro-4-[(2-oxocyclopentyl)methyl]phenyl}propanoate 
• 916845-88-0 methyl 2-(4-methyl-2-nitrophenyl)propanoate 
• 29640-90-2 (4-methyl-2-nitro-phenyl)-acetic acid 
• 29640-91-3 methyl 2-(4-methyl-2-nitrophenyl)acetate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of loxoprofen derivatives

Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-{4′-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID.

Palladium-Catalyzed Synthesis of Indoles from 2-Nitrostyrenes

In the presence of palladium salts, oxidation of 2-nitrostyrenes 1 with nitrous acid alkyl esters 2 resulted in the formation of 2-nitrophenylacetaldehyde dialkyl acetals 3.Reductive cyclization of the acetals 3 with iron powder in acetic acid afforded indoles 5 in good yield.

Synthesis of Substituted Indoles via Meerwein Arylation

A new method for the synthesis of substituted indoles is detailed.Meerwein arylation of 4- and 6-substituted 2-nitrobenzenediazonium chlorides with vinyl acetate or vinyl bromide and subsequent reductive cyclization of the resulting adducts affords the corresponding 6- and 4-substituted (CH3, OCH3, Cl, Br, CF3) indoles.The diazonium bisulfates of weakly basic 2-nitroanilines (4-Cl, 6-Br, 4-CF3) gave higher yields of Meerwein arylation adducts than the corresponding diazonium chlorides.Coupling of 2-nitrobenzenediazonium chloride with 2-acetoxy-1-alkenes followed byreductive cyclization affords 2-alkylindoles.